Leandra Gupta

Leandra is an associate in the Tax Group of our Toronto office practicing primarily in the area of tax controversy and litigation. She completed her J.D. at the University of British Columbia and her LL.M  at New York University School of Law, where she was awarded the Flora S. & Jacob L. Newman Award for distinction in the International Tax Program.

In 2017-2018, Leandra clerked at the Tax Court of Canada. In 2018-2019, Leandra was a law clerk to the Honourable Russell Brown of the Supreme Court of Canada.

Prior to joining Osler, Leandra worked at a multinational law firm in New York.


Areas of Expertise

Representative Work

  • Assisted a tech company in challenging a large tax liability assessed by the IRS following a major transaction
  • Assisted a trustee of a foreign trust in a complex U.S. Tax Court litigation

Latest Insights

  • Osler Update May 8, 2024

    Even the dead wouldn’t be spared from Canada’s capital gains hike

    Canada’s proposed increase to its capital gain inclusion rate is likely to impact a wide cross-section of taxpayers, not just the...

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    Even the dead wouldn’t be spared from Canada’s capital gains hike
  • Osler Update Dec 11, 2023

    A new era for the Canadian GAAR

    Canada’s general anti-avoidance rule (GAAR) operates to negate tax benefits arising from “abusive” tax avoidance transactions.

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    A new era for the Canadian GAAR

Media Mentions

  • Media Mentions Nov 20, 2023

    Amendments to GAAR: The new presumption and penalty exception – Canadian Tax Focus

    Two new key features of GAAR introduced by the federal government in draft legislation in August are potentially here to stay.

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Speaking and Writing

Published Work

  • “Implications of the Notice of Non-Compliance and the Compliance Order Penalty”, Canadian Tax Focus, 14:3, August 2024 (with Roger Smith)
  • “Amendments to GAAR: The New Presumption and Penalty Exception”, Canadian Tax Focus, 13:4, November 2023

Credentials

Education

  • New York University School of Law, LL.M., International Tax Law
  • University of British Columbia, J.D.
  • University of British Columbia, B.Sc. (Biology)

Languages

  • English

Professional Affiliations

  • Canadian Bar Association
  • Canadian Tax Foundation
  • Law Society of Ontario
  • New York State Bar Association
  • New York City Bar Association