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Category: GAAR

Deliberate triggering of 55(2) and the GAAR

Posted on: August 22, 2026 Last updated on: August 21, 2026 Written by: John Loukidelis
The CRA accepted that the pre-2024 GAAR did not apply where subsection 55(2) was triggered deliberately. Will the amended GAAR apply to such planning? The authors point out that the economic substance test in subsection 245(4.1), if it applies, is…
Continue reading “Deliberate triggering of 55(2) and the 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…
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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,…
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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…
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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…
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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…
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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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Pleading away privilege

In One York Street Inc. v 2360083 Ontario Limited, 2026 ONCA 176, the Court held that, by putting in issue its state of mind on signing a lease where the state of mind was based in part on legal advice,…
Continue reading “Pleading away privilege”…

Resigning as a director

According to the author, Stevens v R, 2026 TCC 76, is an important reminder of the importance of “objective” evidence for a director’s resignation. Having a resignation witnessed, ensuring that the corporation has updated its records and ensuring that the…
Continue reading “Resigning as a director”…

Build Canada announcements

Oslers has a couple of good posts on its website—here and here—about tax-related “Canada strong” announcements. The CRA, when considering advance tax rulings, will prioritize “nation-building projects”, and the Income Tax Act (Canada) will be amended to permit a new…
Continue reading “Build Canada announcements”…

Receipts from fraudulent investment schemes

In Daniel Sze “Receipts from Fraudulent Schemes: When Are They Taxable?” Canadian Tax Focus 16:3 (August 2026), the author gives an overview of cases that have considered the taxation of amounts a taxpayer receives from a fraudulent “investment”. He notes…
Continue reading “Receipts from fraudulent investment schemes”…

Deductibility of professional fees

In Hypertec Systèmes inc. v Agence du revenu du Québec, 2025 QCCQ 6704, the taxpayer, the administrative entity for a corporate group, incurred about $1.3 million of professional fees in respect of a shareholder dispute that included a claim for…
Continue reading “Deductibility of professional fees”…

Recent Posts

Pleading away privilege

In One York Street Inc. v 2360083 Ontario Limited, 2026 ONCA 176, the Court held that, by putting in issue its state of mind on signing a lease where the state of mind was based in part on legal advice,…
Continue reading “Pleading away privilege”…

Resigning as a director

According to the author, Stevens v R, 2026 TCC 76, is an important reminder of the importance of “objective” evidence for a director’s resignation. Having a resignation witnessed, ensuring that the corporation has updated its records and ensuring that the…
Continue reading “Resigning as a director”…

Build Canada announcements

Oslers has a couple of good posts on its website—here and here—about tax-related “Canada strong” announcements. The CRA, when considering advance tax rulings, will prioritize “nation-building projects”, and the Income Tax Act (Canada) will be amended to permit a new…
Continue reading “Build Canada announcements”…

Receipts from fraudulent investment schemes

In Daniel Sze “Receipts from Fraudulent Schemes: When Are They Taxable?” Canadian Tax Focus 16:3 (August 2026), the author gives an overview of cases that have considered the taxation of amounts a taxpayer receives from a fraudulent “investment”. He notes…
Continue reading “Receipts from fraudulent investment schemes”…

Deductibility of professional fees

In Hypertec Systèmes inc. v Agence du revenu du Québec, 2025 QCCQ 6704, the taxpayer, the administrative entity for a corporate group, incurred about $1.3 million of professional fees in respect of a shareholder dispute that included a claim for…
Continue reading “Deductibility of professional fees”…

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Archives

Categories

Recent Posts

Pleading away privilege

In One York Street Inc. v 2360083 Ontario Limited, 2026 ONCA 176, the Court held that, by putting in issue its state of mind on signing a lease where the state of mind was based in part on legal advice,…
Continue reading “Pleading away privilege”…

Resigning as a director

According to the author, Stevens v R, 2026 TCC 76, is an important reminder of the importance of “objective” evidence for a director’s resignation. Having a resignation witnessed, ensuring that the corporation has updated its records and ensuring that the…
Continue reading “Resigning as a director”…

Build Canada announcements

Oslers has a couple of good posts on its website—here and here—about tax-related “Canada strong” announcements. The CRA, when considering advance tax rulings, will prioritize “nation-building projects”, and the Income Tax Act (Canada) will be amended to permit a new…
Continue reading “Build Canada announcements”…

Receipts from fraudulent investment schemes

In Daniel Sze “Receipts from Fraudulent Schemes: When Are They Taxable?” Canadian Tax Focus 16:3 (August 2026), the author gives an overview of cases that have considered the taxation of amounts a taxpayer receives from a fraudulent “investment”. He notes…
Continue reading “Receipts from fraudulent investment schemes”…

Deductibility of professional fees

In Hypertec Systèmes inc. v Agence du revenu du Québec, 2025 QCCQ 6704, the taxpayer, the administrative entity for a corporate group, incurred about $1.3 million of professional fees in respect of a shareholder dispute that included a claim for…
Continue reading “Deductibility of professional fees”…

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