Sample Chapter Tax and Family Business Succession Planning,

Sample Chapter Tax and Family Business Succession Planning, 3rd Edition Chapter 10: Spinouts

Sample Chapter Tax and Family Business Succession Planning, 3rd Edition Chapter 10: Spinouts The attached sample chapter, which is a work in progress, has been prepared to illustrate the general form and content of the forthcoming volume, Tax and Family Business Succession Planning, 3rd Edition. The contents of the chapter may be subject to change, and may contain grammatical or other editorial errors or omissions. In any event, it does not purport and is not intended to be advice on any particular matter. The authors do not accept any responsibility or liability to any person in respect of anything done or omitted to be done by any such person in reliance, sole or partial, on the whole or any part of the contents of this sample. This sample is made available solely for evaluation purposes.

Chapter 10 1000 Spinouts CONTENTS Paragraph Introduction... 1001 General Example of Spinout Transaction... 1002 Subsection 55(2)... 1003 Significant Exceptions to Subsection 55(2)... 1004 Purifications and Asset Protection Spinouts... 1005 Series of Transactions or Events... 1006 Case Law Series of Transactions/Transactions in Contemplation of Series... 1007 U.K. Case Law... 1008 Canadian Case Law... 1009 Spinouts to Family Members... 1010 Paragraph 55(3)(a) and Related Provisions... 1011 Examples of Spinouts... 1012 Example 3: Spinout to Family Trust... 1013 Example 4: Spinout to Children... 1014 Series of Transactions... 1015 1001 Introduction At various points during the life of a business and a succession plan, it will be advisable to effect a divisive reorganization whereby the assets of a corporation are spun out into sister corporations or to a holding company. A 413 1001

414 Tax and Family Business Succession Planning spinout transaction contemplates the division of a corporation s assets among its shareholders in a series of tax-deferred transfers. Within the context of succession planning, some of the reasons for such a spinout are as follows: (a) Asset Protection. To enhance the protection of particular assets from creditor claims. For example, if real estate or other valuable investment assets are held in the same corporation as business operations subject to potential creditor risk, it may be advisable to spin these out to a separate sister corporation. (b) Spinout to Certain Family Members. To divide up the corporation s assets, e.g., so that specific assets will be held by a particular family member. As will be seen later in the Chapter, this can be difficult to achieve, short of a true proportional butterf ly. Alternatively, a spinout reorganization might be used, for example, to cash-out Freezor so that the children can operate the business. (c) Small Business Corporation Status. In order to maintain status as a small business corporation. This status is essential in order to utilize a number of provisions under the Act, including the capital gains exemption. (For further discussion, reference should be made to 1005.) (d) Wholesale Division. To split the frozen corporation amongst the children, for example, after the death of the Freezor. Unfortunately, one instance in which this may be advisable is if the succession plan has not worked and there are various assets which the children now wish to split-up amongst themselves and go their separate ways. A spinout reorganization might also be effected prior to a sale to a third party, e.g., to remove assets not to be sold and/or to ensure that the corporation s shares qualif y for the capital gains exemption. For some examples of spinouts in this context, reference should be made to 1012. 1002 General Example of Spinout Transaction The objective of a butterf ly-t ype transaction is to separate the interests of shareholders and in effect demerge the corporation. For example, an operating corporation with a number of businesses or properties might be owned by t wo holding companies, with equal shareholdings, that wish to 1002

Ch. 10/Spinouts 415 separate their interests. The operating corporation might wind up and distribute one-half of its assets to each holding company, which would then continue as independent operating companies. This procedure may not be feasible if the assets have appreciated in value over cost (or have other deferred tax exposure), because of the operation of subsection 69(5). In this case, a butterf ly transaction might be adopted. Suppose, for example, that t wo individual shareholders, Mr. Louis and Ms. Prasad, each own 50% of the shares of an operating company ( Opco ) and wish to separate their interests. They might undertake the following procedure: Example 1 (a) Each shareholder would form a holding company (Louis Holdco, and Prasad Holdco, respectively) to which he or she would transfer shares of Opco, making an election under subsection 85(1). (b) As shown in Figure X, Opco would transfer one-half of its assets to each of these holding companies in consideration for shares (and possibly a note receivable from the holding companies), making elections under subsection 85(1). The shares of the holding companies held by Opco would have a paid-up capital which would not exceed the cost amount of the assets of Opco (net of assumed liabilities). 1 (c) Louis Holdco and Prasad Holdco would redeem their shares held by the operating company producing a deemed dividend to the operating company but no capital gain. (d) Opco would wind up, distributing its assets (cash or notes of the holding companies) to the holding companies, producing a deemed dividend to the holding companies but not a capital gain. 1 Subsection 85(2.1), which normally restricts paid-up capital to the elected amount, is subject to section 84.1 and section 212.1, neither of which is applicable here. 1002

416 Tax and Family Business Succession Planning Figure X Mr. Louis Ms. Prasad Louis Holdco Prasad Holdco 50% Common 50% Common Preferred Shares Preferred Shares Assets Opco Assets If structured properly, the entire transaction would take place free of tax. The deemed dividends would not be taxed by virtue of the intercorporate dividend deduction found in subsection 112(1). As will be seen shortly, the proper structuring of the foregoing transaction involves the avoidance of subsection 55(2), which potentially transmogrifies the deemed dividends mentioned above into deemed capital gains. Note: In the foregoing example, it is possible to transfer Opco s assets directly into Louis Holdco and Prasad Holdco, respectively because neither of these corporations controls Opco; other wise, corporate law issues arise, forcing a more complex reorganization. 1002

Ch. 10/Spinouts 417 1003 Subsection 55(2) Central to such a divisive reorganization is the potential application of subsection 55(2) of the Act. Essentially, subsection 55(2) provides that intercorporate dividends, which would generally pass free of tax under Part I of the Act, pursuant to subsection 112(1), will be treated as capital gains to the recipient if received as part of a transaction or series of transactions, the purpose of which or in the case of a dividend pursuant to subsection 84(3), the result of which was to effect a significant reduction in the capital gain that would have been realized on a sale of shares at fair market value, assuming the dividend had not been paid. It is important to realize that by virtue of subsection 248(10), a dividend declared in contemplation of a series of steps to effect a reduction in what would other wise be a capital gain, may also lead to the tax results described under subsection 55(2). Safe Income. Subsection 55(2) does allow an inter-corporate taxable dividend to pass tax-free, provided it is wholly paid out of income earned or realized (per subsection 55(2)), by the payor corporation after 1971, after the acquisition of the shares on which the dividend is paid (or deemed to be paid) and before safe income determination time, (which is determined with reference to certain transactions within the series of transactions or events in question). This income is referred to as safe income. 2 The CRA has discussed the components of safe income and, in general, the application of subsection 55(2) in a number of instances. See especially Robertson, Capital Gains Strips: A Revenue Canada Perspective on the Provisions of Section 55, Canadian Tax Foundation 1981 Conference Report, 81; Hiltz, Section 55: An Update, 1984 CMTC 40; and Read, Section 55: A Review of Current Issues, Canadian Tax Foundation 1988 Conference Report, 18:1. The CRA takes the position that any portion of a dividend which is derived from non-safe income will cause the entire dividend to be considered a capital gain. Consequently, it is imperative that a thorough calculation of safe income be done before any dividends are declared where a third party sale might occur. It is important to realize that safe income does not necessarily equal the retained earnings of the corporation. In calculating the safe income of the corporation or of particular shares of the corporation, the guidelines in 2 Per subsection 55(1), safe-income determination time for a transaction or event or a series of transactions or events means the time that is the earlier of: (a) the time that is immediately after the earliest disposition or increase in interest described in any of subparagraphs (3)(a)(i) to (v) that resulted from the transaction, event or series, and (b) the time that is immediately before the earliest time that a dividend is paid as part of the transaction, event or series. 1003

418 Tax and Family Business Succession Planning the above-noted articles should be followed, as well as the statutor y requirements of subsection 55(5). Safe income is pro-rated over all shares outstanding at the time the dividend is paid. The first dividends paid on a share come from the share s safe income. Thus, it is possible to pay a series of dividends in order to minimize the possibility that a portion of a dividend comes from unsafe earnings. In the alternative, paragraph 55(5)(f) allows a dividend to be designated as two separate dividends. The CRA has indicated that it would accept multiple paragraph 55(5)(f) designations if there was reasonable doubt as to different components of safe income. 3 In the case of uncertainty, therefore, where a dividend is paid, it should be designated as a number of dividends so that as much as possible of the dividend will be considered to be paid out of safe income. 1004 Significant Exceptions to Subsection 55(2) Apart from dividends paid out of the safe income, subsection 55(3) contains t wo significant exceptions to subsection 55(2): Paragraph 55(3)(a) is generally directed at limiting the operation of subsection 55(2) in cases where the reorganization is part of a transaction or event, or a series of transactions or events where there is not a sale or other disposition of assets on a rollover basis to an unrelated person, 4 nor a transaction that increases such a person s percentage or value of a corporation. The subsection imposes a number of technical tests pertaining to unrelated persons (as defined in subsection 55(3.01)), all of which must be met in order for the exception to subsection 55(2) (which other wise triggers deemed capital gains) to be applicable. It should be noted that the paragraph 55(3)(a) exemption may not be applicable in a number of situations which might normally be considered to be within a related person milieu. 3 CRA Doc. No. ACC9323, August 14, 1990. This Technical Interpretation adds restrictions that were not expressed by Michael Hiltz in his 1984 Corporate Management Tax Conference paper Section 55: An Update, in Selected Income Tax Aspects of the Purchase and Sale of a Business, 1984 Corporate Management Tax Conference (Toronto: Canadian Tax Foundation, 1984). 4 I.e., a person who is unrelated to the dividend recipient. 1004

Ch. 10/Spinouts 419 For a summar y of paragraph 55(3)(a) and related provisions, reference should be made to 1011. Paragraph 55(3)(b) contains the so-called butterf ly exception. This provision essentially allows a corporation to distribute its assets among its shareholders, so long as each shareholder receives its proportional share of each type of property of the corporation. The CRA has stated that there are essentially three types of property: cash and near cash, business assets, and investment assets. The intricacies of paragraph 55(3)(b) are beyond the scope of this book. For more information on the butterfly transaction, see Sider & Ton-That, Understanding Section 55 and Butter f ly Reorganizations (CCH Canadian Limited, 1999). In most situations where family business succession planning is involved, a spinout will be accomplished through the paragraph 55(3)(a) exemption if possible. For one thing, while paragraph 55(3)(a) certainly can have complexities in certain situations (especially where spinouts to family members are involved), paragraph 55(3)(b) is even more complex and, as mentioned above, is limited to a proportional division of assets. The intricacies of the paragraph 55(3)(a) exception come into play where there are issues as to whether unrelated persons are involved in a transaction, particularly spinouts to family members. In this respect, it should be noted that, for the purpose of section 55, siblings are deemed to be at arm s length and unrelated to one another so that the spinout of assets to children could be quite problematic, short of a full-scale proportional butterf ly. Before getting into such intricacies, let us deal with examples where the parties to the reorganization are related. This tends to be the case for capital gains purifications (where no third-part y sale is contemplated, at least) and asset-protection spinouts, as these may involve that split-up of corporatelevel assets where the shareholder is a single individual or spouses. 1005 Purifications and Asset Protection Spinouts If it is desired to keep the operating company in existence and simply purif y it for the purposes of the small business corporation rules/capital gains crystallization, or spinout assets to achieve a degree of asset 1005

420 Tax and Family Business Succession Planning protection, as illustrated in Figures A and B, a paragraph 55(3)(a) spinout could be implemented as follows. Example 2 (a) A new holding company ( Newco ) would be incorporated with both common shares and a fixed number of preferred shares, whose redemption amount would equal the fair market value of the consideration received on the first issuance of the preferred shares (the Newco Redemption Amount). (b) The operating corporation s ( Opco ) share capital would be reorganized pursuant to subsection 86(1) so that the existing issued common shares owned by the shareholder(s) are changed into for new common shares and preferred shares, whose redemption value would equal the fair market value of the assets to be transferred (the Opco Redemption Amount ). (c) Opco would transfer its investment assets to Newco in exchange for all of Newco s preferred shares pursuant to subsection 85(1), at an elected amount equaling the cost amount of those assets i.e., no immediate tax consequences (see Figure A). (d) The preference shares of Opco would be rolled into Newco under subsection 85(1) in exchange for common shares in Newco for an elected amount equal to the cost base of the preferred shares, usually low (see Figure B). (e) Newco would redeem its preferred shares held by Opco in consideration for a non-interest bearing demand promissor y note, the principal amount of which would be the Newco Redemption Amount (the Newco Note ). (f ) Opco would redeem its preferred shares held by Newco, in exchange for the cancellation of the Newco Note. ( g) There will be a tax-free inter-corporate dividend under subsection 84(3) to Newco and Opco for the excess of the redemption proceeds over the paid-up capital of the preferred shares. 1005

Ch. 10/Spinouts 421 Figure A David Common Shares Preferred Shares Opco Preferred Shares Investment Assets Newco Figure B David Common Shares Common Shares Opco Preferred Shares Preferred Shares Newco Investment Assets Notes: When Opco reorganizes its share capital under subsection 86(1), and there is a significant cost base in the pre-existing common shares of Opco, it would be averaged pro rata as to the fair market value in the course of the section 86 reorganization. The cost base allocable to the redeemable/retractable shares would disappear as a result of the rollover of those shares by Opco to Newco pursuant to subsection 85(1) (as noted in paragraph (d) above, and their consequent redemption (per paragraph (e)). 1005

422 Tax and Family Business Succession Planning One way of eliminating this problem would be to issue the preferred shares as a so-called high-low stock dividend, so that the cost base of the common shares would not average with the preferred shares. The significance of low stated capital is that this will minimize the deemed dividend by virtue of the issuance of the preferred shares, since this is based on the increase in stated capital thereof. In some provinces, e.g., British Columbia, it is clear that a high-low stock dividend can be paid. In others, such as Ontario and Alberta, there has in the past been some debate as to whether this is permissible under corporate law. Consequently, both provinces have recently passed legislation which eliminates the uncertaint y. The Newco and Opco redemption amounts are based on the fair market value of the non-business assets of Opco. This number is partially based on the fair market value of Opco. The value of an operating company is not a hard and fast science, and any value may be open to dispute by the CRA. Therefore, it is advisable to utilize special shares (as noted in the above example) rather than common shares so as to be able to have formula redemption and price adjustment clauses in the event that there is a dispute in the value of the non-business assets. 5 The result of the foregoing transactions would be that the investments would be owned by Newco, and the business assets would be owned by Opco. Opco would then meet the definition of a small business corporation in the event that a cr ystallization of the capital gains exemption is desired. In addition, the removal of investment assets will hopefully result in an additional degree of asset protection. It should be noted that, because it does not involve a pro rata distribution of different t ypes of properties, this last example contemplates a paragraph 55(3)(a) situation e.g., where there is only one owner-manager. Where there is more than one (unrelated) owner-manager, the abilit y to utilize the purification process outlined may be restricted, for example, due to the application of subparagraph 55(3)(a)(ii), which, in essence, knocks out the paragraph 55(3)(a) exemption when there is a significant increase in the interest in any corporation of persons unrelated to the corporation prior to the butterfly. The CRA has taken the position that a significant increase in a corporation can be either a proportionate increase or a dollar value increase. In the multiple owner-manager situation, the incorporation of Newco and the transfer of shares to Newco by each owner-manager could be interpreted as a significant increase of each owner-manager in Newco. If this 5 However, as noted at 210, it appears that the CRA is not willing to recognize the effect of a price adjustment clause in connection with shares issued pursuant to a stock dividend freeze on the basis that the stock dividend freeze does not involve a transfer of property in a non-arm s length transaction (see Doc. No. 2003-0004125, April 1, 2003 (French only)). 1005

Ch. 10/Spinouts 423 is the case, the inter-corporate deemed dividends on the cross-redemption of shares may fall afoul of subsection 55(2), and be deemed to be capital gains. It should be noted in this regard that siblings are considered to deal at arm s length and be unrelated to each other by virtue of paragraph 55(5)(e). 6 As stated previously, two objectives of the type of reorganization depicted above could be maintenance of small business corporation status and asset protection. Small Business Corporation ( SBC ): SBC status has become increasingly significant due to various income tax provisions which depend on this status. Besides being a prerequisite for the small business capital gains exemption, it is also significant with respect to the following: the corporate attribution rules; allowable business investment losses; the 10-year reserve for intergenerational transfers; and the capital gains deferral for investments in small business per recently enacted section 44.1. A small business corporation (defined in subsection 248(1)) must, first of all, be a Canadian-controlled private corporation. Second (subject to subsection 110.6(15), which refers to the valuation of life insurance policies and proceeds and ignoring net income stabilization accounts), all or substantially all of the fair market value of the assets of the corporation must be attributable to assets that are: used principally in an active business carried on primarily in Canada by the corporation or a corporation related to it. The meaning of the term active business as presently found in subsection 125(7) applies to this paragraph (see section 248(1) active business definition): shares or indebtedness of one or more small business corporations that are connected (see below) 7 with the particular corporation; or any combination of the assets described above. 6 There was some initial concern as to whether the CRA would apply GA AR to this method of purification. Paragraph 15 of Information Circular IC 88-2 provides an example of a situation in which a corporation was purified. The CRA indicated that GA AR would not be applied in the particular circumstances described. The example did not mention the use of section 85 rollovers to defer taxable gains on appreciated assets in the course of implementing the purification procedures. However, purifications involving section 85 rollovers have generally become accepted practice. 7 Within the meaning of subsection 186(4) on the assumption that the small business corporation is at the time a payer corporation within the meaning of that subsection. 1005

424 Tax and Family Business Succession Planning Basically, a corporation is connected with another corporation if it controls that other corporation (within the extended meaning of subsection 186(2) of the Act) or owns more than 10% of the voting issued share capital and shares representing a fair market value in excess of 10% of the total fair market value of all issued capital of that corporation. The CR A uses a 90% or more benchmark in respect of the all or substantially all test. (For further discussion, reference should be made to 402, Chapter 4, Capital Gains Exemption, Cr ystallization & Multiplication, et seq.) Asset Protection. It should be noted that, if asset protection is an objective of the transaction, certain transfers of propert y discussed in the foregoing discussion may be subject to the various statutor y provisions that are intended to protect creditors interests. In the above discussion, it should be noted that the butterf lies basically involve the spin out of corporate assets through the redemption of shares, i.e., vis-à-vis holding companies which may be formed to receive the assets. Accordingly, the solvency tests found in subsection 32(2) of the OBCA relating to the redemption of shares would come into play where the shares involved in the butterfly are redeemable. If the shares involved are not redeemable, there is also a solvency test under subsection 30(2) of the OBCA relating to the reacquisition of such shares by the corporation. If the solvency tests are not met, there could be directors liabilit y within subsection 130(2) of the OBCA, or the violation could form the basis of an oppression action by creditors. Even if these solvency tests are met, there is also the possibilit y that aggrieved creditors could bring other actions. (For further discussion, reference should be made to Chapter 7, Asset Protection; the solvency tests of various provisions of the OBCA are summarized at 708a.) Note on Part IV Tax Where there is a cross-redemption of shares, as shown in the above examples, the effect of refundable tax balances should be considered carefully. The CRA has taken the position that where the two corporations are connected, as would t ypically be the case with a purification, a crossredemption of shares causes a cascade effect with respect to Part IV tax and dividend refunds: where a dividend refund is generated on a redemption, there will be corresponding Part IV tax to the recipient corporation. The redemption of the recipient corporation s shares, in turn, generates a dividend refund, based at least in part on such Part IV tax. This in turn enlarges Part IV tax to the first corporation, thus enlarging its dividend 1005

Ch. 10/Spinouts 425 refund and therefore the amount of Part IV tax to the recipient corporation, and so on. The result a mathematical iterative (circular) calculation whereby the dividend refund and Part IV tax cascade appears to generate significant Part IV tax/dividend refund. (A similar calculation was upheld by the Tax Court of Canada in Les Entreprises Michele L Heureux Inc. v. The Queen, 94 DTC 1693.) One possible solution to this Part IV tax problem would be to structure the transaction so that the cross-redemption of shares could straddle a yearend. One share redemption would happen before the year-end and the other after. The ordering of redemptions would depend on where the taxpayer wanted the RDTOH to end up. In a typical purification, the paid-up capital will be lower in the corporation which is being purified: the paid-up capital of the recipient corporation will normally ref lect the cost base of assets transferred (see subsection 85(2.1)). Under these circumstances, the corporation with the higher paid-up capital (t ypically the recipient) will experience a significant net liability for Part IV tax, while the payor corporation will enjoy a net dividend refund. Although it appears that the net result is self-cancelling, it should be remembered that there could be cash f low problems/opportunities, e.g., due to differing year-ends and so on. It further appears that if the deemed dividends in respect of both corporations are equal, the final position (when the reorganization is considered in isolation, at least) may be that each corporation will experience a self-cancelling liabilit y for Part IV tax equal to its dividend refund and that each corporation will continue to have a balance of RDTOH at the beginning of its next fiscal period equal to its opening balance before the butterf ly transaction. In this respect, it may be possible to limit or reduce the recipient corporation s paid-up capital under applicable corporate law, such that the amount of the deemed dividend generated by each corporation would be identical. Of course, the foregoing is not a problem if there is no refundable tax balance to begin with. (There may be different effects depending on whether both corporations are connected with one another, or dividends are paid other than as a result of the butterfly.) For further discussion of the cascade effect see Part IV Complications in Butterfly Transactions, Christopher J. Potter, 1992 Canadian Tax Journal, Vol. 4, p. 992 et seq. 1005

426 Tax and Family Business Succession Planning 1006 Series of Transactions or Events As stated previously, the so-called paragraph 55(3)(a) exemption may be critical to a spinout. Central to this is the concept of whether the purification is part of a series of transactions involving a sale or other disposition of assets on a rollover basis to an unrelated person, or a transaction that increases such a person s percentage or value of a corporation. Subsection 248(10) states that a series of transactions or events will include any related transactions or events completed in contemplation of the series. The CRA appears to take a very wide view of the application of subsection 248(10). The following is CR A s standard response regarding the issue: A preliminar y transaction will form part of a series determined with reference to subsection 248(10) if, at the time the preliminary transaction is carried out, the taxpayer intends to implement the subsequent transactions constituting the series, and the subsequent transactions are eventually carried out. Thus, the preliminar y and subsequent transactions will be part of a series even though at the time of the completion of the preliminary transaction the taxpayer either had not determined all the important elements of the subsequent transactions including, possibly, the identity of other taxpayers involved or had lacked the ability to implement the subsequent transactions. 8 The CRA s views on this and related issues are also discussed in Hiltz, Section 245 of the Income Tax Act, Canadian Tax Foundation 1988 Conference Report, 7:1; Robertson, Capital Gains Strips: A Revenue Canada Perspective on the Provisions of Section 55, Canadian Tax Foundation 1981 Conference Report, 81; Hiltz, Section 55: An Update, Canadian Tax Foundation 1984 Cor porate Management Tax Conference, 40; and Read, Section 55: A Review of Current Issues, Canadian Tax Foundation 1988 Conference Report, 18:1. The CRA has also commented as to the application of subsection 248(10) in a technical interpretation involving three scenarios regarding tax-free inter-corporate dividends included in a series of transactions designed to purif y a corporation. 9 1. The shareholders have no intention to sell their shares in the next three years. 8 Revenue Canada Round Table, 1992 APFF Conference, Question 39. 9 See, for example, Michael Hiltz, Section 245 Update in Report of Proceedings of the Fortieth Tax Conference, 1988; Conference Report (Toronto: Canadian Tax Foundation, 1989) 7:1-9, at 7:6; CRA Doc. No. 9237670, December 23, 1992. See also Doc. No. AC57939, June 30, 1989, among others. 1006

Ch. 10/Spinouts 427 2. The shareholders have not identified a purchaser and there is a general intention to sell the shares in the next three to five years. 3. The shareholders have identified a purchaser and it is anticipated that the shareholders will sell their shares within the year. The CRA s response was as follows: 1. In situation 1, the fact that the shareholders have no intention of selling their shares within the next three years is not conclusive that the receipt of the dividends is not part of the series which includes an eventual sale of the shares to an arm s length person. The facts of each particular situation would have to be reviewed to determine whether subsection 55(2) would apply to the series of transactions. 2. Where, at the time the dividends are received the shareholders have an intention to sell their shares, the purification and the eventual sale, would generally be considered to be part of the same series of transactions determined with reference to subsection 248(10), not withstanding the fact that the shareholders had not identified a purchaser and that the eventual sale may not be completed for several years. 3. The purification and the eventual sale, in such a situation, would be considered to be part of the same series of transactions, determined with reference to subsection 248(10), since the shareholders intend to sell their shares and a purchaser had been identified at the time of the reorganization. Within the context of purification transactions, such expansive views on the application of subsection 55(2) by virtue of the series of transaction provisions are premised on the notion that, in most situations, a shareholder who causes a purification reorganization to be carried out does so in order that the capital gains exemption will be available upon a disposition of the shares. In such cases, the shareholder would therefore have some intention at the time of the reorganization of eventually selling the shares. 10 With respect to the potential application of the general anti-avoidance rule in subsection 245(2), the CR A referred to paragraph 15 of Information Circular 88-2, which provides that a transaction entered into to purif y a corporation is within the scheme of the Act, and accordingly, 10 See Doc. No. 5-7939, June 30, 1989. See also notes to the introductory portion of 414a for further comments on the CRA s view of the application of subsection 248(10) in the context of a purification. 1006

428 Tax and Family Business Succession Planning subsection 245(2) would not normally be applied to the claim for the capital gains exemption. 1007 Case Law Series of Transactions/Transactions in Contemplation of Series Besides continually emerging Canadian case law on series of transactions and transactions in contemplation of a series, there is considerable U.K. case law on the former issue. In fact, as elaborated below, the Canadian law in this area is very much influenced by U.K. case law. 1008 U.K. Case Law The English courts have considered the concept of a pre-ordained series of transactions in a series of cases 11 which focus on the concept that the series must be pre-ordained, in essence, conf ining a series of transactions to a situation where it was practically certain that the other steps would follow; only then could it be said that the steps were pre-ordained. This would not be the case if the terms on which the subsequent steps are to take place are not settled at the time of the first. The common law interpretation of the phrase series of transactions in the English cases was adopted by the Federal Court of Appeal in OSFC Holdings Ltd. v. The Queen, 2001 DTC 5471. However, as discussed below, the current state of the law appears to be that subsection 248(10) significantly extends the common law meaning of this phrase. 1009 Canadian Case Law At time of writing, the Supreme Court of Canada had rendered two simultaneous decisions that defined series of transactions in connection with the general anti-avoidance rule (subsection 245(2)). 12 Both decisions were substantially consistent with the law as previously decided in the U.K. courts as well as the Court of Appeal in OSFC. 13 In fact, the ruling in OSFC remains entrenched in the heart of the Supreme Court s rulings. 11 Including Furniss v. Dawson, [1984] A.C. 474 (H.L.) and Craven v. White, [1989] A.C. 459 (H.L.). These cases are discussed in some detail by John Tiley, in his article, Series of Transactions, Canadian Tax Foundation 1988 Conference Report, 8:1. 12 Canada Trustco Mortgage Co. v. Canada, 2005 DTC 5523 and Mathew v. Canada, 2005 DTC 5538. Because of the nature of the transaction in issue, the third Supreme Court of Canada GA AR case, Lipson et al. v. The Queen, 2009 DTC 5015, said little about series of transactions and subsection 248(10). 13 I.e., ignoring subsection 248(10). 1007

Ch. 10/Spinouts 429 In OSFC, which also considered the concept in connection with the general anti-avoidance rule (subsection 245(2)), the Federal Court of Appeal indicated that subsection 248(10) broadened the meaning of series from that defined in the British cases. The OSFC case involved a series of transactions whereby mortgages in loss positions were transferred to a partnership. After this series was completed, a buyer (OSFC) was found which was not identified at the time of the series. OSFC became the majority interest partner and then syndicated its interest in the partnership. The Federal Court of Appeal held that the introduction of the buyer was in contemplation of the series of transactions involving the formation of the partnership. In other words, the concept of contemplation includes a retroactive reference to a previous series. In respect of series of transactions, Rothstein, J. stated: I would, subject to subsection 248(10), adopt the House of Lords approach. Thus, for there to be a series of transactions, each transaction in the series must be pre-ordained to produce a final result. Pre-ordination means that when the first transaction of the series is implemented, all essential features of the subsequent transaction or transactions are determined by persons who have the firm intention and ability to implement them. That is, there must be no practical likelihood that the subsequent transaction or transactions will not take place [paragraph 24]. In respect of subsection 248(10), Rothstein, J. stated: Subsection 248(10) requires three things: first, a series of transactions within the common law meaning; second, a transaction related to that series; and third, the completion of the related transaction in contemplation of that series [paragraph 35]. Thus, before applying subsection 248(10), series must be construed according to its common law meaning, which I have found to be preordained transactions which are practically certain to occur. To that is added any related transactions or events completed in contemplation of the series. Subsection 248(10) does not require that the related transaction be pre-ordained. Nor does it say when the related transaction must be completed. As long as the transaction has some connection with the common law series, it will, if it was completed in contemplation of the common law series, be included in the series by reason of the deeming effect of subsection 248(10). Whether the related transaction is completed in contemplation of the common law series requires an assessment of whether the parties to the transaction k new of the common law series, such that it could be said that they took it into account when deciding to complete the transaction. If so, the transaction can be said to be completed in 1009

430 Tax and Family Business Succession Planning contemplation of the common law series [paragraph 36 emphasis added]. 14 The appellant in OSFC had filed leave to appeal to the Supreme Court of Canada, however, the Supreme Court declined to grant leave. The Supreme Court s decision in Canada Trustco echoed OSFC and said: The meaning of the expression series of transactions under s. 245(2) and (3) is not clear on its face. We agree with the majority of the Federal Court of Appeal in OSFC and endorse the test for a series of transactions as adopted by the House of Lords that a series of transactions involves a number of transactions that are pre-ordained in order to produce a given result with no practical likelihood that the pre-planned events would not take place in the order ordained : Craven v. White, [1989] A.C. 398, at p. 514, per Lord Oliver; see also W.T. Ramsay Ltd. v. Inland Revenue Commissioners, [1981] 1 All E.R. 865 [paragraph 25]. However, the Supreme Court then expanded on the interpretation of in contemplation found within the definition of series of transaction in subsection 248(10) and said: Section 248(10) extends the meaning of series of transactions to include related transactions or events completed in contemplation of the series. The Federal Court of Appeal held, at para. 36 of OSFC, that this occurs where the parties to the transaction knew of the... series, such that it could be said that they took it into account when deciding to complete the transaction. We would elaborate that in contemplation is read not in the sense of actual knowledge but in the broader sense of because of or in relation to the series. The phrase can be applied to events either before or after the basic avoidance transaction found under s. 245(3). As has been noted: It is highly unlikely that Parliament could have intended to include in the statutor y definition of series of transactions related transactions completed in contemplation of a subsequent series of transactions, but not related transactions in the contemplation of which taxpayers completed a prior series of transactions [paragraph 26 emphasis added]. Thus, the knew of and took it into account language articulated in OFSC were subject to the elaboration that in contemplation is read not in the sense of actual knowledge but in the broader sense of because of 14 In Doc. No. 2002-0173345, December 3, 2002, the CRA indicated that the OFSC decision is consistent with the CRA s longstanding interpretation, as expressed by the standard response quoted earlier. 1009

Ch. 10/Spinouts 431 or in relation to an articulation of a functional relationship. However, this left very little guidance as to the degree of nexus. In MIL (Investments) S.A. v. Canada, 2006 DTC 3307, Justice Bell tried to clarif y the foregoing by indicating that there must be a strong nexus bet ween the transactions (paragraph 65); however, as discussed below, this authorit y is now questionable. As a consequence of the Supreme Court rulings, the current state of the law remains that subsection 248(10) expands the scope of the phrase series of transactions beyond the common law def initions of English cases to include any related transactions or events completed in contemplation of the series. However, the Supreme Court of Canada revised the common law definition to allow for the event to occur either before or after the transaction. In the wake of the OSFC decision, the CRA issued Income Tax Technical News No. 22 and Technical Interpretation No. 2002-0173345, December 3, 2002, in which it reaffirmed its prior administrative positions concerning the meaning of the phrase series of transactions for purposes of subsection 248(10) that have been described above. The CRA was also of the opinion that the ruling in OSFC was consistent with its position. The CR A has not elaborated on this issue since the Supreme Court s decisions was rendered. Addendum. In Copthorne Holdings v. The Queen, 2007 DTC 1230 (T.C.C.), contemplation of a series of transactions for the purposes of subsection 248(10) related to a previous series 15 involving the preservation of paid-up capital in certain corporate-group reorganizations which, in the judge s view, resulted in a double count of paid-up capital. The Court indicated the subsequent redemption of shares which cr ystallized the benefit of the high paid-up capital (the impetus of which was a subsequent change to the FAPI rules unforeseen at the time of the first series) had a strong nexus to the previous series; it was completed in contemplation of the previous series, within the meaning of subsection 248(10). By virtue of the concept of backwards contemplation, a series could be extended to include a subsequent transaction, even if unforeseen at the time of the prior series. This concept could adversely affect a variet y of tax planning transac- 15 The statement of professor D.G. Duff in Judicial Application of the General Anti- Avoidance Rule in Canada: OSFC Holdings Ltd. v. The Queen, 57 I.B.F.D. Bulletin 278, at p. 287 (as cited at paragraph 26 of Canada Trustco) was noted: It is highly unlikely that Parliament could have intended to include in the statutory definition of series of transactions related transactions completed in contemplation of a subsequent series of transactions, but not related transactions in the contemplation of which taxpayers completed a prior series of transactions. 1009

432 Tax and Family Business Succession Planning tions, e.g., if designed to preserve/enhance favourable tax attributes in the event that a transaction which might benefit therefrom might come along in the future. (The fact that a transaction may have an independent purpose and existence, apart from the series, does not mean that is excluded if it had been intended to achieve a composite result.) 16 The Federal Court of Appeal affirmed the Tax Court of Canada decision. 17 The Court effectively expanded the series of transactions concept by disapproving of the strong nexus test bet ween the series of transactions itself and transactions in contemplation of the series by looking to a motivating factor test: In my view, if a series is a motivating factor with respect to the completion of a subsequent transaction, the transaction can be said to have been completed in contemplation of the series and a direct causal relationship between the series and the transaction, as argued by the appellant, need not be established. In my opinion, this standard is reconcilable with the test as stated in OSFC and as broadened in Canada Trustco [paragraph 46]. 18 The Court also noted the relatively close temporal connection bet ween the transactions in question, indicating that: While I do not wish to suggest that any particular length of time between a series and a transaction will be determinative..., it is my view that an approximately one year gap between the 1993 Share Sale and the completion of the 1995 Redemption militates against accepting an assertion that there was an extreme degree of remoteness that the 1995 Redemption would be undertaken, as was urged upon the Court [paragraph 51]. Obviously, the issue of whether a series is a motivating factor with respect of the completion of a subsequent transaction will only increase the uncertainty in respect of the series of transactions issue. One may be tempted to conclude that if the prior series of transactions results in a potential tax advantage, this would likely be a motivating factor with respect to the completion of a subsequent transaction. 16 See paragraph 42. 17 2009 DTC 5101. 18 In the preceding paragraph, the Court approved of the statement in MIL that in contemplation, as used in subsection 248(10), does not lead to the conclusion that the mere possibility of a connection between a series of transactions and a related transaction is sufficient to include that transaction in the series. 1009

Ch. 10/Spinouts 433 1010 Spinouts to Family Members The foregoing discussion assumes that the spinout is bet ween related parties, so that the paragraph 55(3)(a) exemption is applicable (assuming that series of transactions/transactions in contemplation of a series is not in issue). However, the prospect of a spinout reorganization in favour of a family member raises more significant complexities with respect to the application of the paragraph 55(3)(a) exemption, without which the only alternative may be a full-scale 55(3)(b) proportional butterf ly. 1011 Paragraph 55(3)(a) and Related Provisions The paragraph 55(3)(a) exemption from subsection 55(2) would generally not apply to a purification, if it is part of a series of transactions that includes a sale or other disposition of assets on a rollover basis to an unrelated person or a transaction that increases such a person s percentage or value of a corporation. However, as stated previously, for the purpose of section 55, siblings are deemed to be at arm s length and unrelated to one another so that the spin out of assets to children could be quite problematic, short of a full-scale proportional butterf ly. Other issues may arise where a family trust is involved, especially if a distribution from such a trust is part of the series of transactions involving a spinout. In such situations, the intricacies of paragraph 55(3)(a) and related provisions must be reviewed ver y carefully. More precisely, paragraph 55(3)(a) provides that subsection 55(2) (deemed capital gains) will apply where, as part of a series of transactions or events as a part of which a dividend was received, there was at any particular time, any of the following: (i) Disposition of property to unrelated person A disposition of property for proceeds 19 that are less than its fair market value to a person (or partnership) that was an unrelated person immediately before the particular time, other than money disposed of on the payment of a dividend or on a reduction of the paid-up capital of a share. (As 19 Under paragraph 55(3.01)(d), the definition of proceeds of disposition is altered for the purposes of paragraph 55(3)(a). Proceeds of disposition, in these circumstances, are to be determined without reference to paragraph 55(2)(a), as provided for in paragraph (j) of the definition in section 54 of the Act (and section 93, per former Bill C-10). Non-residents are deemed, for the purposes of paragraph 55(3)(a), to have disposed of property for proceeds of disposition less than its fair market value, notwithstanding any other provision of the Act, where the gain or loss from the disposition is not included in computing the person s taxable income earned in Canada. The exception to this rule provided for under paragraph 55(3.01)(e), is where, under the laws of the country in which the person is resident, the gain or loss is computed as if the property were disposed of for proceeds that are not less than its fair market value and the gain or loss so computed is recognized for the purposes of the those laws. 1011

434 Tax and Family Business Succession Planning observed below, unrelated person means a person unrelated to the dividend recipient.) (ii) Significant increase in direct interest in any corporation by unrelated person A significant increase in the direct interest in any corporation of any persons (or partnerships) that were unrelated persons immediately before the particular time, other than an increase that arises as a consequence of a disposition of shares of a corporation for proceeds not less than the fair market value of such shares. (iii) Disposition of dividend payer to unrelated person A disposition to a person (or partnership) who was an unrelated person immediately before the particular time, of either shares of the corporation that paid the dividend (the dividend payer) or property 20 which derived more than 10% of its value from shares of the dividend payer. (iv) Disposition of dividend recipient to unrelated person A disposition, after the time the dividend was received, to a person (or partnership) who was an unrelated person immediately before the particular time, of either shares of the dividend recipient or property which derived more than 10% of its value from shares of the dividend recipient. (v) Significant increase in direct interest of unrelated person in dividend payer A significant increase in the total of all direct interests in the dividend payer of any persons (or partnerships) who were unrelated persons immediately before the particular time. Unrelated Person. Subsection 55(3.01) defines unrelated person immediately before the particular time, to mean a person (other than the dividend recipient) to whom the dividend recipient is not related or a partnership, any member of which (other than the dividend recipient) is not related to the dividend recipient. Significant Increase. It will often be difficult to determine whether there has been a significant increase in the interest of an unrelated person in any corporation. It is the view of the CRA that a significant increase is measured in terms of dollar value as well as percentage interest. Also the reference to an interest in a corporation may go beyond share ownership to include ownership of debt of a corporation or any other rights which give the unrelated person a claim on the corporation s assets or revenues. The CRA has consistently taken the position that interest should not be 20 Other than shares of the dividend recipient, per former Bill C-10. 1011

Ch. 10/Spinouts 435 restricted to ownership of shares; the term should describe the economic interest that a person has in the assets held by a corporation and is therefore broad enough to include an indirect interest. 21 Deeming Rules. The rules for determining whether people are related are set out in section 251. However, there are several deeming rules in paragraph 55(5)(e): (i) Siblings not related Brothers and sisters are deemed to deal at arm s length and not to be related. (ii) Trusts A person who is related to every beneficiary of a trust (other than a registered charity) who is or may (other wise than by reason of the death of another beneficiary of the trust) be entitled to share in the income or capital of the trust is deemed to be related to the trust (and if the person is also a benef iciar y, the person is deemed for these purposes to be related to himself or herself ). (iii) Tr usts and beneficiaries A beneficiar y of a trust and the trust are deemed not to be related unless the beneficiary receives a share owned by the trust in satisfaction of all or part of his or her interest in the trust, or if the beneficiary is a corporation controlled by the trust, or if the beneficiary and trust are related by virtue of (ii) above. (iv) Rights/connective relationship not applicable Persons who are related solely by virtue of paragraph 251(5)(b) (rights to acquire shares, etc.), or subsection 251(3) (t wo corporations are related to one another if they are related to the same corporation) are deemed not to be related to each other. Anti-Avoidance. Subsection 55(4) contains a further rule that may deem persons not to be related or deem a corporation not to be controlled if it is reasonable to consider that one of the main purposes of one or more transactions was to cause the persons to be related or a corporation to be controlled and thus make subsection 55(2) inapplicable. Interpretative Provisions. Paragraph 55(3.01)(b) provides that for the purposes of paragraph 55(3)(a), a corporation that is formed by an amalgamation of two or more predecessor corporations, is deemed to be the same 21 See M. Ton-That & V. Sider, Understanding Section 55 and Butterf ly Reorganizations (1999, CCH Canadian Limited, North York), page 68. See also John Robertson Capital Gains Strips; A Revenue Canada Perspective on the Provisions of Section 55 in Report of Proceedings of the Thirty-Third Tax Conference, 1981, Conference Report (Toronto: Canadian Tax Foundation, 1982), 81-109, at 105, Question 28; and Peter K. Rogers, CGA, Splitting Up and Reorganizing the Family Business Some Tips and Traps, 2001 British Columbia Tax Conference ( Vancouver: Canadian Tax Foundation, 2001), 8:1-30. 1011

436 Tax and Family Business Succession Planning corporation as, and a continuation of the predecessor corporations. Similarly, paragraph 55(3.01)(c) provides that where a subsidiar y is wound up into its parent corporation in circumstances to which subsection 88(1) is applicable, the parent corporation is deemed, for the purposes of paragraph 55(3)(a), to be the same corporation as, and a continuation of the subsidiar y. Related Persons. Related persons are defined in subsection 251(2) for the purposes of the Act, as follows: (a) individuals connected by blood relationship, marriage or common-law partnership or adoption; (b) a corporation and (i) a person who controls the corporation, if it is controlled by one person, (ii) a person who is a member of a related group that controls the corporation, or (iii) any person related to a person described in subparagraph (i) or (ii); (c) any two corporations (i) if they are controlled by the same person or group of persons, (ii) if each of the corporations is controlled by one person and the person who controls one of the corporations is related to the person who controls the other corporation, (iii) if one of the corporations is controlled by one person and that person is related to any member of a related group that controls the other corporation, (iv) if one of the corporations is controlled by one person and that person is related to each member of an unrelated group that controls the other corporation, (v) if any member of a related group that controls one of the corporations is related to each member of an unrelated group that controls the other corporation, or (vi) if each member of an unrelated group that controls one of the corporations is related to at least one member of an unrelated group that controls the other corporation. 1011

Ch. 10/Spinouts 437 1012 Examples of Spinouts As stated previously, spinouts to family members and the like must be reviewed carefully to ensure that the paragraph 55(3)(a) exemption applies; other wise the spinout must be effected as a full-scale proportionate butterfly. 1013 Example 3: Spinout to Family Trust Figures C and D illustrate a spinout to a family trust which many practitioners take for granted. As shown in Figure C, David (father) is assumed to hold freeze shares of Hoots-Paw Holdings redeemable/retractable at $500,000, with common shares held by the Louis Family Trust, having a fair market value of $1 million. For convenience, we are assuming that Hoots-Paw Holdings holds $500,000 of investment assets and all of the shares of Subco, which also has a FMV of $1 million. The purpose of this reorganization could be a capital gains exemption purification, or asset protection, for example. Figure C David Louis Louis Family Trust Freeze Shares $500,000 Common Shares FMV $1M Hoots-Paw Holdings Subco FMV $1M 1013

438 Tax and Family Business Succession Planning The spinout reorganization is shown in Figure D. The Louis Family Trust would roll its common shares of Hoots-Paw Holdings into Trust Holdco pursuant to section 85 of the Act. David would hold thin-voting shares of a Trust Holdco, i.e., to retain control. The idea of the spinout would be for Hoots-Paw Holdings to transfer its shares of Subco into Trust Holdco, in return for redeemable/retractable shares based on the FMV of Subco. The inter-corporate shareholdings as bet ween Hoots-Paw Holdings and Trust Holdco would, of course be redeemed; e.g., the consideration for the redemption would be promissor y notes, which would then be set off against one another. The redemption would involve deemed dividends in both corporations. Therefore, both Hoots-Paw Holdings and Trust Holdco would be dividend recipients. Figure D David Louis Thin-Voting Shares Louis Family Trust Freeze Shares Hoots-Paw Holdings Common Shares Trust Holdco? Subco 1013

Ch. 10/Spinouts 439 Accordingly, the unrelated person tests applies with respect to both Hoots-Paw Holdings and Trust Holdco. Generally, however, a spinout reorganization will qualif y if each of the parties are related to one another, since all of the provisions of paragraph 55(3)(a) will be satisfied in such case. Louis Family Tr ust/david. Per paragraph 55(5)(e), the Louis Family Trust will be related to David Louis if David Louis is related to each beneficiary (other than a registered charity) under a trust who is or may (other wise than by reason of the death of another beneficiary under the trust) be entitled to share in the income or capital of the Louis Family Trust. If the beneficiaries of the Louis Family Trust are the issue of David, or the issue of David and his spouse Mia, this would be the case. As noted, it is also possible to include a registered charit y as a beneficiar y. If, however, the benef iciaries included a sibling, niece, or nephew of David, the Louis Family Trust would not be related to David. There would also be a problem if a charity other than a registered charit y were named as a beneficiar y. Registered charities generally pertain to Canadian-resident institutions, per subsection 248(1); this means, for example, that a foreign charit y would throw the trust offside, unless the charity could only be entitled to income or capital by virtue of the death of the beneficiaries (this might be the case if the charity was named the beneficiary if all of the other benef iciaries passed away i.e., as a default clause). Louis Family Tr ust/hoots-paw. The Louis Family Trust is related to Hoots-Paw Holdings by virtue of subparagraph 251(2)(b)(iii), since it is related to the person who controls Hoots-Paw Holdings, David Louis. Louis Family Trust/Trust Holdco. The Louis Family Trust is related to Trust Holdco by virtue of subparagraph 251(2)(b)(iii) since it is related to the person who controls Trust Holdco, David Louis. If, however, subsection 55(4) were to apply, one must determine whether the Louis Family Trust would other wise be related to Trust Holdco. Per subparagraph 55(5)(e)(iii), a trust and a person shall be deemed not to be related unless they are deemed by paragraph 55(3.2)(d) or subparagraph 55(5)(e)(ii) to be related to each other, or 1013

440 Tax and Family Business Succession Planning the person is a corporation that is controlled by the Trust. It would appear that the last part of subparagraph 55(5)(e)(iii) would apply. 22 Hoots-Paw/Tr ust Holdco. Hoots-Paw Holdings and Trust Holdco are related because David controls both corporations. If, however, the anti-avoidance rule in subsection 55(4) applies, and David s thinvoting shares are ignored, Hoots-Paw Holdings and Trust Holdco are related by virtue of subparagraph 251(2)(c)(ii), since each corporation is controlled by one person and the person who controls Trust Holdco (Louis Family Trust) is related to the person who controls Hoots-Paw (David). David Louis/Hoots-Paw. David is related to Hoots-Paw because he controls this corporation. David Louis/Tr ust Holdco. David is related to Trust Holdco, either because he controls it, or if subsection 55(4) (anti-avoidance) applies, by virtue of subparagraph 251(2)(b)(iii), since Trust Holdco is controlled by the Louis Family Trust and David is related to the Louis Family Trust. 1014 Example 4: Spinout to Children Figure E and Figure F illustrate a reorganization which, until fairly recently, could have been effected under the paragraph 55(3)(a) exemption. In Figure E, it is assumed that David (Father) holds voting freeze shares of Hoots-Paw Holdings Limited redeemable/retractable at $500,000, with Adam and Alyssa (David s children) holding common shares worth the same amount. Hoots-Paw Holdings Limited holds shares of Davidco (an operating corporation), Adamco (also an operating corporation) and Alyssaco (an investment corporation). Because Adamco and Davidco are operating corporations whereas Alyssaco is an investment corporation, it is not pos- 22 This is on the simplistic assumption that if subsection 55(4) applies, the shares in question are ignored. This would leave the shares held by the Louis Family Trust; as long as these carry some votes, the Louis Family Trust would control Trust Holdco. However, the application of subsection 55(4) does not explicitly result in the deemed non-existence of the shares in question. Presumably, however, if Trust Holdco would other wise be related to the Louis Family Trust i.e., because the Louis Family Trust would other wise control Trust Holdco were it not for the thin-voting shares, one would think that it would follow that one of the main purposes of the thin-voting shares would not be to cause Trust Holdco to be related to David Louis i.e., so that the spinout could have other wise been affected. Accordingly, arguably, none of the main purposes was to pre-empt the application of subsection 55(2), so that the thin-voting shares would not be subject to subsection 55(4). 1014

Ch. 10/Spinouts 441 sible to spinout Alyssaco to Alyssa Holdings as a true proportional butterf ly. For convenience, we have assumed that each of Davidco, Adamco, and Alyssaco is worth $500,000, the value of the common shares held by Adam and Alyssa respectively. Figure E David Adam Alyssa Freeze Shares FMV $500,000 Common Shares FMV $500,000 Common Shares FMV $500,000 Hoots-Paw Holdings Limited FMV $500,000 FMV $500,000 FMV $500,000 Davidco (Opco) Adamco (Opco) Alyssaco (Investco) As illustrated in Figure F, the object of the reorganization is for Adam to form Adam Holdings, Alyssa to form Alyssa Holdings, and then spin out the shares of Adamco and Alyssaco to these holding companies. It should be remembered that, for the purposes of section 55, siblings are deemed to be at arm s length and unrelated to one another. 1014

442 Tax and Family Business Succession Planning Figure F David Adam Alyssa Freeze Shares Common Shares Common Shares Common Shares Adam Holdings* Hoots-Paw Holdings*? Common Shares Alyssa Holdings*? Davidco Adamco Alyssaco * Dividend Recipient Among other things, this reorganization would involve a disposition of property at less than fair market value to both Adam Holdings and Alyssa Holdings. Adam Holdings and Alyssa Holdings are both dividend recipients, as is Hoots-Paw Holdings. The problem is that Adam Holdings and Alyssa Holdings must be related to each other, since this is determined in reference to the dividend recipient (i.e., per subparagraph 55(3)(a)(i) there is a disposition at less than fair market value to a person Adam Holdings which is unrelated to the dividend recipient, Alyssa Holdings, and vice versa). Although Adam Holdings and Alyssa Holdings are related to Hoots-Paw Holdings by virtue of subparagraph 251(2)(b)(ii), they are not related to one another, since, for the purposes of section 55, each corporation is controlled by an unrelated person, Adam and Alyssa respectively. Until recently, Adam Holdings and Alyssa Holdings would be deemed to be related through subsection 251(3) of the Act, a connective provision which deems t wo corporations to be related to each other if they are related to the same corporation, i.e., Hoots-Paw Holdings. However, per subparagraph 55(5)(e)(iv), this provision no longer applies to section 55. 1014

Ch. 10/Spinouts 443 As shown in Figure G, however, ignoring subsection 55(4) (discussed below), it appears to be possible to effect the spinout if David controlled Hoots-Paw Holdings, Adam Holdings and Alyssa Holdings i.e., if it is a complete series of transactions that is, not part of a larger series of transactions involving an unrelated person (or in contemplation thereof ). 23 Figure G David Adam Alyssa Voting Shares Common Shares Common Shares Freeze Shares (Voting) Common Shares Adam Holdings Voting Shares Hoots-Paw Holdings? Common Shares Alyssa Holdings*? Davidco Adamco Alyssaco * Dividend Recipient The foregoing example illustrates that spinout reorganizations can be effected on a non-proportional basis if a parent controls all of the 23 In this case, since Hoots-Paw Holdings, Adam Holdings and Alyssa Holdings are controlled by the same person David they would now be related to one another, per subparagraph 251(2)(c)(i). Further, while Adam/Adam Holdings and Alyssa/Alyssa Holdings would no longer be related to each other by virtue of being controlled by Adam and Alyssa respectively, they would be related to each other by virtue of subparagraph 251(2)(b)(iii), and Adam and Alyssa would also be related to Hoots-Paw Holdings by virtue of this provision. Thus, while Adam and Alyssa continue to be unrelated to one another, they are now related to all three corporations which are the dividend recipients. 1014

444 Tax and Family Business Succession Planning corporations, thus underscoring the need to effect such reorganizations while a parent is still alive. However, subsection 55(4) may well throw the reorganization offside i.e., where it can be reasonably considered that one of the main purposes of one or more transactions is to cause two or more persons to be related to one another or to cause a corporation to control another corporation so that subsection 55(2) is not applicable. Where a parent is to retain a significant equit y interest in corporations into which assets have been spun out, some rulings have represented that the purpose of the parent controlling such corporations is to provide him/her with a continuing source of dividends and/or to protect the parent s economic interests. Other rulings have contained a representation that none of the main reasons for a parent controlling such corporations is to cause the corporations to be related. 1015 Series of Transactions In order to determine whether the paragraph 55(3)(a) exemption applies, it is important to determine parameters of the particular series of transactions, which, as stated above, includes transactions in contemplation of the series. For example, the transaction contemplated above might have been preceded by a distribution of the common shares of Hoots-Paw Holdings to Adam and Alyssa from a family trust, e.g., as a result of the impending 21st anniversar y of the trust. If this distribution were considered to be part of the same series of transaction as the spinout to Adam and Alyssa, the distribution itself would involve the disposition of propert y at less than fair market value, i.e., the rollout of the shares of Hoots-Paw Holdings from the trust. It must then be determined whether the person to whom the disposition was made (Adam and Alyssa) was unrelated to the dividend recipients at the time of the distribution. This may raise issues as to the applicability of the subparagraph 55(3)(a) exemption. If, however, in the foregoing example, Hoots-Paw, Adam Holdings and Alyssa Holdings were controlled by David, Adam and Alyssa would be related to the dividend recipients, ignoring the subsection 55(4) anti-avoidance rule. However, it is possible that a distribution from the trust could have been made to a third party, who was unrelated to the dividend recipients at the time of the distribution. Even if this is 1015

Ch. 10/Spinouts 445 not the case, other technical issues may arise. 24 Generally, where the paragraph 55(3)(a) exemption is to be relied on, great care should be taken in respect of transactions which could be linked to the reorganization. 24 If a dividend recipient, e.g., Adam Holdco, did not exist at the time of the distribution of common shares from the family trust, it is quite possible that Adam would not be related to Adam Holdco. This depends on whether there is a positive or negative test implied in the interpretation of paragraph 55(3.01)(a). Under a positive test, it would be necessary that, at the particular time, the person be related to the dividend recipient. If the dividend recipient did not yet exist, this would not be the case and the test would not be satisfied. Under the negative test, the person would not be an unrelated person in respect of a dividend recipient as long as the recipient is not not related at the particular time. Therefore, if the dividend recipient does not yet exist at the particular time, the negative test would be satisfied: while the person (Adam) would not be related to Adam Holdco (because it does not yet exist), the person is not unrelated. In any event, it might be possible to incorporate Adam Holdco (and other dividend recipients) prior to the distribution from the family trust, so that at the time of the distribution, Adam Holdco would exist and thus be related to Adam. 1015

Tax and Family Business Succession Planning, 3rd Edition The successful transfer of a family business from one generation to the next is notoriously difficult. In Tax and Family Business Succession Planning, authors David Louis, Samantha Prasad and new co-author Michael Goldberg, of Minden Gross LLP, provide an in-depth discussion of the myriad tax and non-tax issues facing accountants and lawyers addressing family business succession planning. Updated to reflect budgetary pronouncements, legislative changes and new case law, including: Control premium issues Valuation of discretionary trust Planning for the 21st anniversary of a Trust Shareholder agreements relating to buy-outs on deaths Association rules and trusts/choice of executor New developments in distributions to non-residents Estates and acquisition of control rules Published: October 2009 Book No. B212 List Price: $90.00 www.cch.ca/b212sc Abbreviated Table of Contents Chapter 1 Introduction to Tax and Family Business Succession Chapter 2 Estate Freezes Chapter 3 Trusts Chapter 4 Capital Gains Exemption, Crystallization & Multiplication Chapter 5 Income Splitting Chapter 6 Tax Treatment of Life Insurance Chapter 7 Asset Protection Chapter 8 Wills and Will Substitutes Chapter 9 Freezes: Alterations, Variations and Trust Distributions Chapter 10 Spinouts Chapter 11 Shareholder s Agreements: Family-Business Constitution? Chapter 12 Death of First Generation Post-Mortem Planning Topical Index The Estate Planner s Handbook, 3rd Edition The Estate Planner s Handbook provides a concise yet comprehensive overview of some of the most important issues in the estate planning process. It is particularly recommended for lawyers, accountants and other professional advisors who are new to this growing field or who have more experience but seek a handy guide to issues outside their particular area of expertise. New with this edition is a chapter on estate planning for the disabled that, among other things, addresses the relation of planning vehicles provided by the Income Tax Act (such as Life Time Benefit Trusts and Registered Disability Savings Plans) and Henson trusts designed to safeguard access to provincial income support programs. Topics addressed in this edition: Wills Multiple Wills Will Substitutes Continuing Powers of Attorney Health and Personal Care by Proxy Some Basic Trust Law Concepts & Principles Taxation of Basic Trusts Used in Estate Planning Certain Other Trusts Used in Estate Planning Charitable Donations Taxation at Death United States Estate & Gift Tax Probate Dependants Relief Spousal Property Rights in Ontario Published: September 2009 Book No. B170 List Price: $110.00 www.cch.ca/b170sc

ORDER FORM Product Format Item No. Price Qty. Total Tax and Family Business Succession Planning, 3rd Edition Book B212 $90.00 The Estate Planner s Handbook, 3rd Edition Book B170 $110.00 Shipping & handling charges and applicable taxes are extra. Prices are subject to change without notice. Please Quote CCH Code TFBSP902 PAYMENT OPTIONS Bill My Account American Express MasterCard Visa CCH Account No. Card No. Expiry Date Signature CUSTOMER INFORMATION Name Firm Area of Specialty Title Professional Designation Address City Province Postal Code Telephone No. Fax No. Email Address FIVE ways to order Telephone Toll Free: 1 800 268 4522 Toronto: 416 224 2248 Fax Toll Free: 1 800 461 4131 Toronto: 416 224 2243 E-mail cservice@cch.ca Website www.cch.ca/b212sc www.cch.ca/b170sc Mail CCH Canadian Limited 300 90 Sheppard Avenue East Toronto, Ontario M2N 6X1 M569-9-09

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