Cases
Canada (The King) v. MICROBJO PROPERTIES INC., 2023 FCA 157
The taxpayers, who were holding companies for partnerships that had recently agreed to sell their farmlands to third parties, were approached by...
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| Tax Topics - Income Tax Act - Section 160 - Subsection 160(1) | a transaction that split, on the purchaser’s terms, a tax savings purportedly generated by it, was a non-arm’s length transaction | 701 |
| Tax Topics - Income Tax Act - Section 251 - Subsection 251(1) - Paragraph 251(1)(c) | parties were not dealing at arm's length in transactions where they did not put their own patrimony in play | 370 |
| Tax Topics - Statutory Interpretation - Interpretation Act - Subsection 45(2) | subsequent amendment confirmed the prior state of the law | 82 |
| Tax Topics - Income Tax Act - Section 160 - Subsection 160(5) | s. 160(5) did not change the prior view that prior facts could be taken into account | 96 |
2763478 Canada Inc. v. Canada, 2018 FCA 209
Prior to the sale of a corporation ("Groupe AST") to a third party, its individual shareholder (“Jobin”) transferred his shares of Groupe AST...
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| Tax Topics - Income Tax Act - Section 248 - Subsection 248(10) | 9 month separation did not avoid series | 290 |
| Tax Topics - Income Tax Act - Section 245 - Subsection 245(4) | value shift transactions that permitted the absorption of a real gain by a paper loss abused the basic capital gains regime | 317 |
| Tax Topics - Income Tax Act - Section 245 - Subsection 245(6) | individual allegedly suffering double taxation re s. 245(2) denial of capital loss of his corporation failed to apply under s. 245(6) within 180 days | 327 |
Canada v. Spruce Credit Union, 2014 DTC 5079 [at 7044], 2014 FCA 143
The taxpayer and 53 other BC credit unions maintained their required deposit insurance with two corporations ("CUDIC" and "STAB"). Due to a...
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| Tax Topics - Income Tax Act - Section 137.1 - Subsection 137.1(4) - Paragraph 137.1(4)(c) | allocations in proportion to shareholdings rather than premiums | 304 |
1207192 Ontario Limited v. Canada, 2012 DTC 5157 [at 7396], 2012 FCA 259, aff'g 2011 DTC 1301 [at 1686], 2011 TCC 383
In the course of applying s. 245 to deny the recognition by the taxpayer of a capital loss, the Court considered and rejected the argument of the...
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| Tax Topics - Income Tax Act - Section 245 - Subsection 245(4) | capital loss from value shift did not reflect economic loss; purpose objectively determined | 451 |
Canada Safeway v. Alberta, 2012 DTC 5133 [at 7271], 2012 ABCA 232
The taxpayer implemented a series of transactions that gave rise to interest deductions in Alberta, with the interest income being received free...
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| Tax Topics - Income Tax Act - Section 245 - Subsection 245(4) | replacing equity with borrowed money to reduce provincial income not abusive | 285 |
Canada v. Mackay, 2008 DTC 6238, 2008 FCA 105
In order for the taxpayers to acquire an interest in a shopping centre, a bank which held mortgages on the centre that were in foreclosure...
Canada v. Canadian Pacific Ltd., 2002 DTC 6742, [2002] 3 F.C. 170, 2002 FCA 98
The taxpayer borrowed 216 million in Australian dollars under debentures bearing interest at 16.125% per annum and that had been issued at a 2%...
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| Tax Topics - Income Tax Act - Section 245 - Subsection 245(4) | transaction not to be recharacterized until after a determination of abuse | 283 |
| Tax Topics - Income Tax Act - Section 245 - Subsection 245(1) - Transaction | an aspect of a transaction is not a transaction | 249 |
OSFC Holdings Ltd. v. Canada, 2001 DTC 5471, 2001 FCA 260
After becoming insolvent, a company ("Standard") in the mortgages business established a partnership, transferred a mortgage portfolio to the...
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| Tax Topics - Income Tax Act - Section 245 - Subsection 245(4) | policy against corporate loss trading | 229 |
| Tax Topics - Income Tax Act - Section 248 - Subsection 248(10) | 32 | |
| Tax Topics - Statutory Interpretation - Interpretation Bulletins, etc. | 70 | |
| Tax Topics - Statutory Interpretation - Interpretation/Definition Provisions | deeming v. definition provisions | 46 |
See Also
Husky Energy Inc. v. The King, 2023 TCC 167
Before a Canadian public corporation (“Husky”) paid a dividend on its shares, two significant shareholders of Husky resident in Barbados (the...
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| Tax Topics - Treaties - Income Tax Conventions - Article 10 | recipient of dividends on borrowed shares was not their beneficial owner because of requirement to pay dividend compensation payments | 270 |
| Tax Topics - Income Tax Act - Section 212 - Subsection 212(2) | tax under s. 212(2) imposed on the basis of payment of dividend to a non-resident rather than on the basis of who is the beneficial owner | 405 |
| Tax Topics - Income Tax Act - Section 245 - Subsection 245(1) - Tax Benefit | no tax benefit under s. 215(6) from targeted reduced rate of dividend withholding if in base transaction, the Canadian dividend payer would have withheld at the higher rate | 347 |
| Tax Topics - Income Tax Act - Section 245 - Subsection 245(4) | the residence, beneficial owner, and voting requirements in the Canada-Luxembourg Treaty fully expressed the rationale for the 5% Treaty-reduced rate on dividends | 413 |
Mony v. The King, 2022 CCI 120
The taxpayer agreed to sell his shares of a Canadian-controlled private corporation (“Créaform”), having a nominal ACB, to third parties. On...
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| Tax Topics - Income Tax Act - Section 245 - Subsection 245(4) | Gervais followed to find that avoiding capital gains attribution through ACB averaging abused ss. 73(1) and 74.2(1) | 380 |
Damis Properties Inc. v. The Queen, 2021 TCC 24
Five corporate taxpayers sought to increase their after-tax return from the sale by their farm partnerships of the farm by transferring their...
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| Tax Topics - Income Tax Act - Section 160 - Subsection 160(1) | s. 160 did not apply to a sale of companies holding cash sales proceeds to a purchaser who purported to eliminate the tax liability | 785 |
| Tax Topics - Income Tax Act - Section 245 - Subsection 245(1) - Tax Benefit | no tax benefit based on comparison to a commercially unrealistic alternative | 276 |
| Tax Topics - Income Tax Regulations - Regulation 1102 - Subsection 1102(1) - Paragraph 1102(1)(c) | software was not acquired with an income-producing purpose | 282 |
| Tax Topics - General Concepts - Onus | unfair to place the onus on taxpayer re facts which taxpayer could not reasonably be expected to know | 339 |
Agence du revenu du Québec v. Custeau, 2020 QCCA 1496
When a family small business corporation (the “Corporation”) was in financial difficulty, two Quebec regional development funds agreed in 1997...
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| Tax Topics - Income Tax Act - Section 248 - Subsection 248(10) | Copthorne does not require the s. 248(10) “in contemplation of” test to be applied on a backwards-looking basis | 695 |
Loblaw Financial Holdings Inc. v. The Queen, 2018 TCC 182, rev'd on s. 95(1) - investment business - (a) (arm's length conduct) grounds 2020 FCA 79, in turn aff'd 2021 SCC 51
The taxpayer, which was an indirect wholly-owned subsidiary of Loblaw Companies Limited (a Canadian public company), wholly-owned a Barbados...
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| Tax Topics - Income Tax Act - Section 165 - Subsection 165(1.11) | requirement met where Crown knew the nature and quantum of the dispute | 269 |
| Tax Topics - Income Tax Act - Section 95 - Subsection 95(1) - Foreign Bank | CFA qualified as a foreign bank since it was licensed under Barbados law as an international bank | 123 |
| Tax Topics - Income Tax Act - Section 95 - Subsection 95(1) - Investment Business - Paragraph (a) | Barbados-licensed international bank, which used Loblaw funding to invest responsively to Loblaw considerations, conducted an offside non-arm’s length business | 429 |
| Tax Topics - Income Tax Act - Section 95 - Subsection 95(1) - Investment Business - Paragraph (c) | employee equivalents was reduced by employee time described in s. 95(2)(b) | 290 |
| Tax Topics - Income Tax Act - Section 9 - Capital Gain vs. Profit - Foreign Exchange | short-term debt securities were inventory because they were the raw material for generating swap income | 130 |
| Tax Topics - Income Tax Act - Section 152 - Subsection 152(4.01) - Paragraph 152(4.01)(a) - Subparagraph 152(4.01)(a)(ii) | GAAR is generally a separate matter rather than being subsumed in the allegedly-misused substantive provision | 208 |
| Tax Topics - Income Tax Act - Section 248 - Subsection 248(10) | hiring of employees 15-years previously to engage foreign bank exception to investment business definition was not part of same series as renewal of foreign bank licence | 228 |
| Tax Topics - Income Tax Act - Section 245 - Subsection 245(4) | use of Barbados sub to engage in proprietary trading for Canadian parent misused the foreign bank exemption, whose purpose was promoting international competitiveness | 336 |
| Tax Topics - Income Tax Act - Section 95 - Subsection 95(2) - Paragraph 95(2)(l) | purpose of s. 95(2)(l) exception was to permit non-resident subsidiaries of Canadian banks and dealers to compete internationally | 190 |
Custeau v. Agence du revenu du Québec, 2018 QCCQ 5692, aff'd 2020 QCCA 1496
The two taxpayers (Charles and Philippe, who were brothers) each subscribed nominal amounts for Class A common shares of the family operating...
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| Tax Topics - Income Tax Act - Section 245 - Subsection 245(4) | no abuse where individuals used PUC thrust upon them by an arm’s length investor (through PUC averaging) to subsequently strip surplus | 298 |
Soucy v. Agence du revenu du Québec, 2018 QCCQ 4845
A direct gift of a vehicle to the taxpayer by her ex-husband would have been subject to Quebec sales tax as they were now unrelated persons. From...
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| Tax Topics - Excise Tax Act - Section 274 - Subsection 274(3) | double gift was made (avoiding QST) because the property would not have been directly gifted | 246 |
Birchcliff Energy Ltd. v. The Queen, 2017 TCC 234
A newly-launched public corporation ("Birchcliff") accessed the losses of a lossco ("Veracel"), in order to shelter the profits from producing oil...
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| Tax Topics - General Concepts - Sham | ephemeral transactions under a Plan of Arrangement were not a sham | 215 |
| Tax Topics - Income Tax Act - Section 251.2 - Subsection 251.2(2) - Paragraph 251.2(2)(a) | proxy which accorded no discretion to a class of shareholders did not render them a group | 221 |
| Tax Topics - Income Tax Act - Section 245 - Subsection 245(4) | raising share equity through a lossco immediately before its amalgamation was abusive | 278 |
2763478 Canada Inc. v. The Queen, 2017 TCC 98, aff'd 2018 CAF 209
Prior to the sale of a corporation ("Groupe AST") to a third party, its individual shareholder rolled his shares of Groupe AST into a holding...
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| Tax Topics - Income Tax Act - Section 245 - Subsection 245(4) | value-shift transactions were abusive | 258 |
Gervais v. The Queen, 2016 TCC 180, aff'd 2018 FCA 3
The taxpayer’s wife (Mrs. Gendron) purchased 1.04M preferred shares from the taxpayer (Mr. Gervais) at a cost of $1.04M (with Mr. Gervais not...
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| Tax Topics - Income Tax Act - Section 245 - Subsection 245(4) | basis averaging scheme to transfer half of a capital gain to the taxpayer’s wife was an abuse of the attribution rules | 429 |
| Tax Topics - Income Tax Act - Section 245 - Subsection 245(1) - Tax Benefit | benefit compared to straight sale and gift | 166 |
Veracity Capital Corporation v. M.N.R., 2015 DTC 5136 [at 6421], 2015 BCSC 2278, rev'd 2017 BCCA 3
The following transactions occurred under a KPMG-advised “Quebec Year-end shuffle” or “Q-Yes” plan in order to avoid 90% of the B.C....
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| Tax Topics - Income Tax Act - Section 245 - Subsection 245(4) | abuse of inter-provincial income allocation formula “designed to prevent both the over-taxation and the under-taxation of income" | 500 |
Birchcliff Energy Ltd. v. The Queen, 2015 TCC 232, nullified on procedural grounds 2017 FCA 89
A newly-launched public corporation ("Birchcliff") accessed the losses of a lossco ("Veracel"), in order to shelter the profits from producing oil...
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| Tax Topics - General Concepts - Sham | transitory share issuance under plan of arrangement was not a sham | 177 |
| Tax Topics - Income Tax Act - Section 111 - Subsection 111(5) - Paragraph 111(5)(a) | grant of proxy did not detract from investors acting individually in own interest | 237 |
| Tax Topics - Income Tax Act - Section 245 - Subsection 245(4) | abusive reverse takeover by Lossco through diverted private placement | 261 |
Pièces automobiles Lecavalier Inc. v. The Queen, 2014 DTC 1126 [at 3319], 2013 TCC 310
A Canadian subsidiary ("Greenleaf") of Ford U.S. paid down to $9,750,000 (including accrued interest) a debt of $24,369,439 (plus accrued...
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| Tax Topics - General Concepts - Evidence | Canadian tax accountant's testimony on US tax consequences accorded little weight | 152 |
| Tax Topics - Income Tax Act - Section 245 - Subsection 245(4) | avoidance of debt forgiveness rules was abusive | 277 |
| Tax Topics - Income Tax Act - Section 248 - Subsection 248(10) | debt-paydown transactions effected in contemplation of sale transaction were part of same series as the sales transactions | 248 |
Swirsky v. The Queen, 2013 TCC 73, 2013 DTC 1078 [at 431], aff'd 2014 FCA 36
For creditor-proofing reasons, the taxpayer sold shares in a family real estate development company ("Torgan") to his wife, and used the sales...
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| Tax Topics - Income Tax Act - Section 245 - Subsection 245(4) | 33 | |
| Tax Topics - Income Tax Act - Section 74.5 - Subsection 74.5(11) | 247 |
McClarty Family Trust v. The Queen, 2012 DTC 1123 [at 3122], 2012 TCC 80
A family holding company ("MPSI") paid a stock dividend of preferred shares, having nominal paid-up capital and a redemption amount of $48,000, on...
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| Tax Topics - Income Tax Act - Section 84 - Subsection 84(3) | 340 |
McMullen v. The Queen, 2007 DTC 286, 2007 TCC 16
The taxpayer and an unrelated individual ("DeBruyn") accomplished a split-up of the business of a corporation ("DEL") of which they were equal...
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| Tax Topics - Income Tax Act - Section 245 - Subsection 245(4) | 198 | |
| Tax Topics - Income Tax Act - Section 251 - Subsection 251(1) - Paragraph 251(1)(c) | mutual benefit and same advisors insufficient to establish non-arm's length in structured sale transaction | 257 |
| Tax Topics - Income Tax Act - Section 84 - Subsection 84(2) | 229 | |
| Tax Topics - Income Tax Act - Section 84.1 - Subsection 84.1(1) | arm's length: negotiation based on self-interest | 257 |
MIL (Investments) S A v. The Queen, 2006 DTC 3307, 2006 TCC 460, aff'd 2007 FCA 236
In March 1993 an individual ("Boulle") transferred his shares of a Canadian public junior exploration company ("DFR") to the taxpayer, which was a...
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| Tax Topics - Income Tax Act - Section 248 - Subsection 248(10) | 230 | |
| Tax Topics - Statutory Interpretation - Retroactivity/Retrospectivity | 91 | |
| Tax Topics - Treaties - Income Tax Conventions | 148 |
Desmarais v. The Queen, 2006 DTC 2376, 2006 TCC 44
The taxpayer, who held 14.28% of the common shares of a Canadian private corporation ("Consercom") transferred a 9.76% block to a wholly-owned...
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| Tax Topics - Income Tax Act - Section 245 - Subsection 245(4) | surplus stripping | 235 |
Overs v. The Queen, 2006 DTC 2192, 2006 TCC 26
The taxpayer owed approximately $2.3 million to a wholly-owned corporation. The loan, which had been used by him for personal purposes, would be...
Univar Canada Ltd. v. The Queen, 2005 DTC 1478, 2005 TCC 723
The taxpayer incorporated a Barbados subsidiary ("BarbadosCo") using borrowed money to subscribe for the shares of BarbadosCo, and BarbadosCo used...
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| Tax Topics - Income Tax Act - Section 95 - Subsection 95(6) - Paragraph 95(6)(b) | no tax avoidance purpose since no base-case intention to have acquired the underlying note | 102 |
Brouillette v. The Queen, 2005 DTC 1004, 2005 TCC 203
The taxpayer facilitated a leveraged buy-out of him and his co-shareholder of a company ("Brouillette Automobiles") by incorporating a corporation...
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| Tax Topics - Income Tax Act - Section 251 - Subsection 251(1) - Paragraph 251(1)(c) | same advisors insufficient/adverse re price | 199 |
Geransky v. The Queen, docket 98-2383(IT)G (TCC)
The taxpayer, who owned a portion of the shares of the holding ("GH") which, in turn, owned an operating company ("GBC") utilized the enhanced...
Husky Oil Ltd. v. R., 99 DTC 308, [1999] 4 CTC 2691 (TCC)
A Bermuda corporation, which was in financial difficulty and in which the taxpayer had an indirect 35% interest, transferred a drilling vessel,...
Commissioner of Taxation of the Commonwealth of Australia v. Spotless Services Ltd., 71 ALJR 81, 34 ATR 183, 141 ALR 92
Under arrangements that were characterized as a deposit of funds by the taxpayer in the Cook Islands, the taxpayer received an interest rate on...
RMM Canadian Enterprises Inc. v. R., 97 DTC 302, [1998] 1 C.T.C. 2300 (TCC)
A non-resident corporation ("EC") approached a business associate who, along with two other individuals, formed a Canadian corporation ("RMM") to...
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| Tax Topics - Income Tax Act - Section 159 - Subsection 159(3) | 167 | |
| Tax Topics - Income Tax Act - Section 245 - Subsection 245(4) | 235 | |
| Tax Topics - Income Tax Act - Section 251 - Subsection 251(1) - Paragraph 251(1)(c) | purchaser of cash-rich company without any signifcant separate role did not deal at arm's length | 177 |
| Tax Topics - Income Tax Act - Section 84 - Subsection 84(2) | application of s. 84(2) to sale of cash-rich company to accommodation party who quickly paid cash proceeds therefor | 222 |
| Tax Topics - Treaties - Income Tax Conventions | 96 | |
| Tax Topics - Treaties - Income Tax Conventions - Article 10 | 116 |
Mark Resources Inc. v. The Queen, 93 DTC 1004, [1993] 2 CTC 2259 (TCC)
Before going on to find that the former s. 245(1) did not prohibit the deduction of interest by the taxpayer, Bowman J. stated, in obiter dicta...
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| Tax Topics - Income Tax Act - Section 20 - Subsection 20(1) - Paragraph 20(1)(c) | loss utilization was not income-producing purpose/ gross income test | 177 |
Barclays Mercantile Industrial Finance Ltd. v. Melluish, [1990] BTC 209 (Ch. D.)
The taxpayer ("BMI") acquired a film from the producer ("WBI"), leased it to another corporation at a return that yielded 2.16% per annum on its...
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| Tax Topics - Income Tax Act - Section 18 - Subsection 18(1) - Paragraph 18(1)(a) - Income-Producing Purpose | 136 | |
| Tax Topics - Income Tax Act - Section 83 - Subsection 83(2.1) | main purpose was to make a profit, not take deduction | 264 |
| Tax Topics - Income Tax Regulations - Regulation 1100 - Subsection 1100(17) | no "lease" where failure to provide exclusive possession | 75 |
Mallalieu v. Drummond, [1983] BTC 380, [1983] 2 All E.R. 1095 (HL)
The court rejected the view that in ascertaining the purpose of an expenditure, the state of mind of the spender is the only relevant factor.
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| Tax Topics - Income Tax Act - Section 18 - Subsection 18(1) - Paragraph 18(1)(h) | 64 |
Newton v. Commissioner of Taxation of the Commonwealth of Australia, [1958] A.C. 450 (PC)
In interpreting the provisions of s. 260 of the Commonwealth Income Tax and Social Services Contribution Assessment Act, 1936-1951 (Australia),...
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| Tax Topics - Income Tax Act - Section 260 - Subsection 260(1) - Securities Lending Arrangement | "arrangement" | 130 |
Administrative Policy
23 May 2013 IFA Round Table Q. 4
Given that in all three cases, a new Canadian corporation (CanHoldco) is "inserted" to establish cross-border PUC so as to enable surplus of...
2003 Ruling 2003-03924
The corporate general partner of a Canadian limited partnership operating a business in Canada borrows on an unsecured basis under a loan with a...
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| Tax Topics - Income Tax Act - Section 212 - Subsection 212(1) - Subparagraph 212(1)(b)(vii) | 100 |
11 October 1996 APFF Roundtable, 7M12910 - APFF ROUND TABLE
In a situation where Canco subscribes for shares of its Barbados subsidiary, and the Barbados subsidiary loans the same funds to a U.S. subsidiary...
Finance
Modernizing and Strengthening the General Anti-Avoidance Rule, Department of Finance Consultation Paper, 11 August 2022
Narrowing “bona fide purpose”
- It may be appropriate to provide that a “bona fide purpose” does not include foreign (or provincial) tax...
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| Tax Topics - Income Tax Act - Section 245 - Subsection 245(1) - Transaction | 60 | |
| Tax Topics - Income Tax Act - Section 245 - Subsection 245(4) | 904 |
Articles
Avery Jones, "Nothing Either Good or Bad, but Thinking Makes it So - The Mental Element in Anti-Avoidance Legislation", 1983 British Tax Review, p. 9, 113.
Paragraph 245(3)(a)
Administrative Policy
8 October 2010 Roundtable, 2010-0373221C6 F - Paid-up capital
CRA indicated that it has concluded in some cases that using PUC averaging to shift PUC to individual shareholders engages GAAR, and “is...
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| Tax Topics - Income Tax Act - Section 245 - Subsection 245(4) | CRA has concluded in some cases that using PUC averaging to shift PUC to individual shareholders engages GAAR | 283 |
| Tax Topics - Income Tax Act - Section 89 - Subsection 89(1) - Paid-Up Capital - Paragraph (a) | abusive use of PUC averaging to shift PUC to individuals | 39 |
Paragraph 245(3)(b)
Administrative Policy
17 May 2023 IFA Finance Update
Change to “one of the main purposes” test modernized the test
- There were suggestions in obiter dicta that, if there is a transaction that...
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| Tax Topics - Income Tax Act - Section 245 - Subsection 245(0.1) | 56 | |
| Tax Topics - Income Tax Act - Section 245 - Subsection 245(4.1) | 260 |