Andrew Stirling 

Andrew Stirling

Toronto
Brookfield Place, Suite 4400
181 Bay Street
Toronto, Ontario M5J 2T3

t: 416.865.7813
e: andrew.stirling@mcmillan.ca

overview

Andrew Stirling is a lawyer in McMillan's Tax Group. He advises domestic and international clients on a wide variety of income tax matters, with a particular emphasis on domestic and international tax planning, ongoing tax compliance and dispute resolution. He also advises First Nations, charities and other not-for-profit entities.

Andrew helps clients to structure and implement domestic and international acquisitions, divestitures, reorganizations and business combinations in a tax-efficient, yet practical, manner. He has considerable experience advising clients on both inbound and outbound expansions. Andrew also assists asset managers to establish and administer investment funds.

Andrew provides clients with ongoing advice on tax compliance and reporting measures associated with carrying on business in Canada. He also makes submissions to the Canada Revenue Agency, the provincial tax authorities and the Tax Court of Canada when disputes arise. He has particular experience in filing voluntary disclosures on his clients' behalf.

Andrew has advised First Nations on the tax-efficient structuring of large infrastructure projects, as well as the settling of capital trusts to preserve and invest payments from government or industry. He also regularly assists clients with the establishment of charities and not-for-profit entities and advises on their ongoing tax compliance and reporting obligations.

Andrew has published articles in a number of publications, including as a regular contributor of case comments to the Canadian Tax Journal. While completing his Master of Laws at Oxford University, he was an Associate Editor of the Oxford University Commonwealth Law Journal.

Presentations

the U.S. - Canada Tax Treaty: Impacts and Planning Opportunities

Publications

Implementing a Cap on Employee Stock Option Deductions
Budget 2019: CRA Refines Mutual Fund Allocation to Redeemers Methodology and Tightens Rules on TFSAs
Partnership Bump Flattened by GAAR
Canada v. Oxford Properties Group Inc.
Budget 2018: Federal Government Targets Transactions by Financial Institutions
Budget 2017: Timing of Recognition of Gains and Losses on Derivatives
Interest Deduction on a Circular Cash Flow Arrangement Allowed
TDL Group Co. v. Canada (FCA)
Budget 2016: Reversal of Previously Announced Tax Exemption for Charitable Donations
Budget 2016: New Rules Governing the Taxation of "Switch Fund" Shares
Number of Voluntary Disclosures Continues to Increase
Windfalls in the Tax Court
Budget 2015: Incentivizing Charitable Giving and Easing Investment Restrictions on Charities and RCAAAs
Budget 2014: Revisions to the Tax on Split Income (the "Kiddie Tax")
Budget 2014: Consultation on Eligible Capital Property
The Taxation of "Egregious or Repulsive" Conduct and the Treatment of Prejudicial, Scandalous, or Abusive Pleadings
Canada: Audit Guide
Budget 2013: international tax compliance
Foreign Tax Deduction Denied for Tower Structure
Canada Unveils Significant Amendments to Thin Cap Regime
Budget 2012: flexibility for eligible dividend designations introduced
Ontario budget 2012: An indication of things to come
Proposed legislative amendments shore up safe harbour for non-resident investment funds
A Matter of Fairness: Cancellation of Interest and Penalties under the Canadian Taxpayer Relief Provisions
Tax Discrimination: Relief Under Canada's Tax Treaties
Zen and the Art of Collecting Interest on Directors' Tax Debts
Change in Canadian tax rules make it easier to invest in Canada
Canada and the U.S. Ratify Significant Tax Treaty Changes
Eligible Financial Contracts vs. Insolvency: Round II
Your guide to the transfer pricing impact of the new Canada-US Protocol

News

McMillan LLP Announces 13 Equity Partner & Partner Promotions
Cluep Completes its Sale to Impact Group
Canadian Counsel to Refresco Group N.V. in its US$1.25 Billion Acquisition of Cott Corporation

Education

  • University of Oxford, M.Jur. - 2009
  • McGill University, BCL/LLB - 2007
  • McGill University, BA - 2003

Year Of Call

  • Called to the Ontario bar - 2008

Practices

tax
business taxation
cross-border taxation
tax litigation and advocacy
charities/not-for-profit/tax-exempts
aboriginal law
investment funds and asset management
cryptocurrency and blockchain

Industries

private equity - buyouts & venture capital investment
banking, finance and insurance
mining
energy
manufacturing, distribution and retail

Directorships and Professional Associations

  • Canadian Tax Foundation
  • International Fiscal Association
  • Ontario Bar Association
  • Canadian Bar Association

Andrew Stirling is a lawyer in McMillan's Tax Group. He advises domestic and international clients on a wide variety of income tax matters, with a particular emphasis on domestic and international tax planning, ongoing tax compliance and dispute resolution. He also advises First Nations, charities and other not-for-profit entities.

Andrew helps clients to structure and implement domestic and international acquisitions, divestitures, reorganizations and business combinations in a tax-efficient, yet practical, manner. He has considerable experience advising clients on both inbound and outbound expansions. Andrew also assists asset managers to establish and administer investment funds.

Andrew provides clients with ongoing advice on tax compliance and reporting measures associated with carrying on business in Canada. He also makes submissions to the Canada Revenue Agency, the provincial tax authorities and the Tax Court of Canada when disputes arise. He has particular experience in filing voluntary disclosures on his clients' behalf.

Andrew has advised First Nations on the tax-efficient structuring of large infrastructure projects, as well as the settling of capital trusts to preserve and invest payments from government or industry. He also regularly assists clients with the establishment of charities and not-for-profit entities and advises on their ongoing tax compliance and reporting obligations.

Andrew has published articles in a number of publications, including as a regular contributor of case comments to the Canadian Tax Journal. While completing his Master of Laws at Oxford University, he was an Associate Editor of the Oxford University Commonwealth Law Journal.

June 2018
Partnership Bump Flattened by GAAR
Canada v. Oxford Properties Group Inc.

First published by the Canadian Tax Foundation in (2018) 66:2 Canadian Tax Journal

November 2016
Interest Deduction on a Circular Cash Flow Arrangement Allowed
TDL Group Co. v. Canada (FCA)

First published by the Canadian Tax Foundation in (2016) 64:3 Canadian Tax Journal.

2015
Interest Deducibility: Navigating the Purpose Test
Canadian Tax Journal, Issue 63(3)
2015
Windfalls in the Tax Court
First published by the Canadian Tax Foundation in the Current Cases feature (2015) 63:1 Canadian Tax Journal 227-39
October 2013
Canada: Audit Guide
World Transfer Pricing 2014 - International Tax Review
June 2012
Foreign Tax Deduction Denied for Tower Structure
Canadian Tax Journal
Issue 60:2
May 2012
Canada Unveils Significant Amendments to Thin Cap Regime
Tax Notes International
Volume 66, Number 9 - May 28, 2012
2011
Tax Discrimination: Relief Under Canada's Tax Treaties
Canadian Tax Journal (2011) Vol 59, No. 2
2010
Zen and the Art of Collecting Interest on Directors' Tax Debts
Canadian Tax Journal (2010) Vol 58, No. 4
Winter 2009
Canada and the U.S. Ratify Significant Tax Treaty Changes
Michigan Tax Lawyer, Volume XXXV, Issue 1, Winter 2009
Co-authored by Michael Friedman and Todd Miller
January 2008
Eligible Financial Contracts vs. Insolvency: Round II
Annual Review of Insolvency Law - 2007 - Janis P. Sarra, Editor
January 2016
Understanding the Basic Building Blocks of the Canadian Foreign Affiliate Rules
25th Foreign Affiliates Course, Federated Press, Toronto, Ontario
May 15, 2014
the U.S. - Canada Tax Treaty: Impacts and Planning Opportunities
Federated Press: Cross-Border Personal Tax Planning