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Category: GAAR

DAC Investment

Posted on: May 8, 2026 Last updated on: April 28, 2026 Written by: John Loukidelis
The authors discuss R v DAC Investment Holdings Inc., 2026 FCA 35, rev’g 2024 TCC 63. They conclude that, in a GAAR analysis, an overly-broad characterization of a provision or a mere description of its effect will not correctly express its object, spirit and purpose…
Continue reading “DAC Investment”…

Harvard Properties detailed notes

Posted on: January 16, 2026 Last updated on: January 16, 2026 Written by: John Loukidelis
Harvard Properties 2024 TCC 139 per Boyle TCJ General procedure Under appeal A-382-24; A-388-24 “Another Section 160 Tax Avoidance Scam: Harvard Properties” Brian Arnold report 296 Jan 14/25 * Facts The following is a paraphrase of the facts set out…
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Accessing stranded ACB ok under GAAR

Posted on: April 10, 2024 Last updated on: April 10, 2024 Written by: John Loukidelis
In 3295940 CANADA INC. v R, 2024 FCA 42, the taxpayer appealed the application of the GAAR to a series of transactions that used ACB in shares of a corporation that the purchaser refused to purchase. The transactions, in effect,…
Continue reading “Accessing stranded ACB ok under GAAR”…

Deans Knight applied

Posted on: December 23, 2023 Last updated on: December 20, 2023 Written by: John Loukidelis
In R v. MMV Capital Partners Inc., 2023 FCA 234, the Court applied GAAR to a scheme where five of the original shareholders of the taxpayer maintained de jure control but an arm’s length party acquired 99% of the corporation’s…
Continue reading “Deans Knight applied”…

GAAR changes bad

Posted on: October 12, 2023 Last updated on: October 12, 2023 Written by: John Loukidelis
Subsection 245(3) will be amended so that a transaction will be an “avoidance transaction” if one of its main purposes is to obtain a tax benefit. Many more transactions will be avoidance transactions because tax considerations always play a major…
Continue reading “GAAR changes bad”…

GAAR object and spirit

Posted on: January 20, 2021 Last updated on: January 20, 2021 Written by: John Loukidelis
The author provides a summary of the detailed analysis undertaken by the Court in Gladwin Realty Corporation v Canada, 2020 FCA 142 to determine the object and spirit of the provisions of the Income Tax Act (Canada) at issue in…
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CDA timing and GAAR

Posted on: July 9, 2019 Last updated on: July 9, 2019 Written by: John Loukidelis
If a corporation triggers a capital gain, pays a capital dividend using the resulting CDA balance and then triggers a capital loss that, in effect, offsets the gain, does the GAAR apply? In Gladwin Realty Corporation v R, 2019 TCC…
Continue reading “CDA timing and GAAR”…

GAAR to be applied only when benefit realized

Posted on: January 4, 2019 Last updated on: January 4, 2019 Written by: John Loukidelis
The CRA, per Wild v R, 2018 FCA 114, accepts that the GAAR can be applied only after the benefit has been realized. Neal Armstrong summary of Alexandra MacLean, “CRA Audits of Large Corporations – The view from ILBD” November…
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Purpose of 84.1

Posted on: October 18, 2018 Last updated on: October 18, 2018 Written by: John Loukidelis
In E Hamelin, “Surplus Stripping: A New Approach?” 18:4 Tax for the Owner-Manager (October 18, 2018), the author notes that the Court in Pomerleau v R, 2018 FCA 129 seemed to treat the one-half portion of a capital gain that…
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GAAR and corporate surplus

Posted on: January 21, 2017 Last updated on: January 21, 2017 Written by: John Loukidelis
In Pomerleau c R, 2016 CCI 228, the Tax Court applied GAAR to a series of transactions that used the stop loss rule in 40(3.6) to create basis not caught by the PUC grind in 84.1, which in turn allowed…
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Related siblings under section 55

At the 2025 APFF conference, the CRA stated that the sisters in the following scenario would be related as per subparagraph 55(5)(e)(i): Sister A and Sister B each owned 100 percent of the shares of their respective holding corporations, whose…
Continue reading “Related siblings under section 55”…

Subsection 55(2) can be good actually

If subsection 55(2) applies to a dividend, and the cash related to the dividend needs to be paid to an individual shareholder anyway, the shareholder will likely be better off compared to the situation obtained when the subsection does not…
Continue reading “Subsection 55(2) can be good actually”…

Loans by a partnership to a partner

The CRA has generally held that a loan from a partnership to a partner will reduce the ACB of the partner’s partnership interest because of the “all-encompassing” language in subparagraph 53(2)(c)(v) of the Income Tax Act (Canada). The CRA has…
Continue reading “Loans by a partnership to a partner”…

Directors of a dissolved corporation

In 2008, I wrote an article for the Hamilton Law Association Journal that, among other things, addressed the status of directors of a corporation that has been dissolved. I referred to Leger v R, 2007 TCC 322, which held that,…
Continue reading “Directors of a dissolved corporation”…

DAC Investment

The authors discuss R v DAC Investment Holdings Inc., 2026 FCA 35, rev’g 2024 TCC 63. They conclude that, in a GAAR analysis, an overly-broad characterization of a provision or a mere description of its effect will not correctly express its object, spirit and purpose…
Continue reading “DAC Investment”…

Recent Posts

Related siblings under section 55

At the 2025 APFF conference, the CRA stated that the sisters in the following scenario would be related as per subparagraph 55(5)(e)(i): Sister A and Sister B each owned 100 percent of the shares of their respective holding corporations, whose…
Continue reading “Related siblings under section 55”…

Subsection 55(2) can be good actually

If subsection 55(2) applies to a dividend, and the cash related to the dividend needs to be paid to an individual shareholder anyway, the shareholder will likely be better off compared to the situation obtained when the subsection does not…
Continue reading “Subsection 55(2) can be good actually”…

Loans by a partnership to a partner

The CRA has generally held that a loan from a partnership to a partner will reduce the ACB of the partner’s partnership interest because of the “all-encompassing” language in subparagraph 53(2)(c)(v) of the Income Tax Act (Canada). The CRA has…
Continue reading “Loans by a partnership to a partner”…

Directors of a dissolved corporation

In 2008, I wrote an article for the Hamilton Law Association Journal that, among other things, addressed the status of directors of a corporation that has been dissolved. I referred to Leger v R, 2007 TCC 322, which held that,…
Continue reading “Directors of a dissolved corporation”…

DAC Investment

The authors discuss R v DAC Investment Holdings Inc., 2026 FCA 35, rev’g 2024 TCC 63. They conclude that, in a GAAR analysis, an overly-broad characterization of a provision or a mere description of its effect will not correctly express its object, spirit and purpose…
Continue reading “DAC Investment”…

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Archives

Categories

Recent Posts

Related siblings under section 55

At the 2025 APFF conference, the CRA stated that the sisters in the following scenario would be related as per subparagraph 55(5)(e)(i): Sister A and Sister B each owned 100 percent of the shares of their respective holding corporations, whose…
Continue reading “Related siblings under section 55”…

Subsection 55(2) can be good actually

If subsection 55(2) applies to a dividend, and the cash related to the dividend needs to be paid to an individual shareholder anyway, the shareholder will likely be better off compared to the situation obtained when the subsection does not…
Continue reading “Subsection 55(2) can be good actually”…

Loans by a partnership to a partner

The CRA has generally held that a loan from a partnership to a partner will reduce the ACB of the partner’s partnership interest because of the “all-encompassing” language in subparagraph 53(2)(c)(v) of the Income Tax Act (Canada). The CRA has…
Continue reading “Loans by a partnership to a partner”…

Directors of a dissolved corporation

In 2008, I wrote an article for the Hamilton Law Association Journal that, among other things, addressed the status of directors of a corporation that has been dissolved. I referred to Leger v R, 2007 TCC 322, which held that,…
Continue reading “Directors of a dissolved corporation”…

DAC Investment

The authors discuss R v DAC Investment Holdings Inc., 2026 FCA 35, rev’g 2024 TCC 63. They conclude that, in a GAAR analysis, an overly-broad characterization of a provision or a mere description of its effect will not correctly express its object, spirit and purpose…
Continue reading “DAC Investment”…

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