Timothy is Co-Chair of the Tax Group and leads the capital markets tax practice at Osler. He advises on a wide range of corporate finance transactions, from traditional IPOs and private placements to innovative financial instruments, including hybrid securities, Basel III compliant capital, securitizations, securities loans, and derivatives.
He acts for Canadian and foreign financial institutions and other capital markets participants, including global investment banks, dealers, exchanges and clearing houses. He provides advice to domestic and offshore hedge funds, pension plans, ETFs, and mutual funds.
Timothy served two terms on the Osler Partnership Board and is Chair of the Firm’s UK Desk.
Areas of Expertise
Representative Work
- Alphabet Inc.
Alphabet in its $8.5-billion inaugural maple bond offering
- The underwriters
BMO Capital Markets, RBC Capital Markets and National Bank Capital Markets in Artemis Gold Inc.’s inaugural $450-million senior unsecured note offering
- The underwriters
The underwriters in the secondary offering of subordinate voting shares of Groupe Dynamite
- Diversified Royalty Corp.
Diversified Royalty Corp. in its $69-million public offering of convertible debentures
- Aritzia Inc.
Aritzia in connection with a $209-million secondary offering of shares
- A syndicate of underwriters
SECURE Waste Infrastructure Corp.'s $300-million senior unsecured notes offering
- A syndicate of dealers
A syndicate of dealers in Keyera Corp.'s $2.3-billion senior notes offering and $500-million hybrid notes offering
- Boyd Group Services Inc.
Boyd Group Services Inc. in its $275-million senior unsecured notes offering
- Aritzia Inc.
Aritzia in connection with a $73-million secondary offering of shares
- A syndicate of underwriters
CIBC Capital Markets and ATB Securities in Bonterra Energy Corp.’s inaugural $135-million senior secured second lien notes offering
- The underwriters
The underwriters, led by Goldman Sachs, BMO Capital Markets, RBC Capital Markets and TD Securities, in connection with the initial public offering by Groupe Dynamite Inc.
- A syndicate of agents
The agents in connection with a $700-million offering of senior notes by Fairfax Financial Holdings Limited
- National Bank Financial Inc.
Tenaz Energy Corp. in its inaugural $140-million senior unsecured notes offering
- A syndicate of underwriters
Surge Energy Inc. in its Inaugural $175 Million Senior Unsecured Notes Offering
- Royal Bank of Canada
Royal Bank of Canada in its $600-million Institutional Preferred Shares Series BW offering
- Royal Bank of Canada
Royal Bank of Canada in its inaugural US$1 billion Limited Recourse Series 4 Capital Notes offering
- A syndicate of underwriters
SECURE Energy Services Inc. in its $300-million high-yield note offering
- First Capital REIT
The agents in connection with First Capital REIT’s offering of $300 million Series B unsecured debentures
- Royal Bank of Canada
Royal Bank of Canada in its $750 million Institutional Preferred Shares Series BU offering.
- The Initial Purchasers
goeasy Ltd. in its closing of an offering of US$550 million senior unsecured notes
- CIBC World Markets
The syndicate of underwriters in the US$2.25 billion bond offering by the Province of British Columbia
- Emera Incorporated
Emera Incorporated in its $500 million senior unsecured note financing
- goeasy Ltd.
The Underwriters in goeasy’s $58 million bought deal offering of common shares
- Mind Medicine
Mind Medicine in its US$30 million public offering
- Lion One Metals Limited
Lion One Metals Limited in its bought deal offering with Eight Capital and Canaccord Genuity Corp.
- Advising Canadian and non-Canadian banks and other corporations in negotiating derivative arrangements (including within the ISDA, GMRA and GMSLA frameworks)
- Advising Canadian public companies on balance sheet and other hedging arrangements
- Advising Canadian tax-exempt investors on the use of derivatives as a substitute for direct investment
- Advising Canadian investment funds and other market participants regarding compliance with tax rules concerning derivative forward agreements, synthetic equity arrangements and synthetic disposition arrangements
- Advising Canadian and international intermediaries on the tax treatment of securities lending transactions with Canadian counterparties and over Canadian securities
- Establishing and restructuring securitization vehicles
Alphabet in its $8.5-billion inaugural maple bond offering
BMO Capital Markets, RBC Capital Markets and National Bank Capital Markets in Artemis Gold Inc.’s inaugural $450-million senior unsecured note offering
The underwriters in the secondary offering of subordinate voting shares of Groupe Dynamite
Diversified Royalty Corp. in its $69-million public offering of convertible debentures
Aritzia in connection with a $209-million secondary offering of shares
- A syndicate of underwriters
SECURE Waste Infrastructure Corp.'s $300-million senior unsecured notes offering
- A syndicate of dealers
A syndicate of dealers in Keyera Corp.'s $2.3-billion senior notes offering and $500-million hybrid notes offering
- Boyd Group Services Inc.
Boyd Group Services Inc. in its $275-million senior unsecured notes offering
- Aritzia Inc.
Aritzia in connection with a $73-million secondary offering of shares
- A syndicate of underwriters
CIBC Capital Markets and ATB Securities in Bonterra Energy Corp.’s inaugural $135-million senior secured second lien notes offering
- The underwriters
The underwriters, led by Goldman Sachs, BMO Capital Markets, RBC Capital Markets and TD Securities, in connection with the initial public offering by Groupe Dynamite Inc.
- A syndicate of agents
The agents in connection with a $700-million offering of senior notes by Fairfax Financial Holdings Limited
- National Bank Financial Inc.
Tenaz Energy Corp. in its inaugural $140-million senior unsecured notes offering
- A syndicate of underwriters
Surge Energy Inc. in its Inaugural $175 Million Senior Unsecured Notes Offering
- Royal Bank of Canada
Royal Bank of Canada in its $600-million Institutional Preferred Shares Series BW offering
- Royal Bank of Canada
Royal Bank of Canada in its inaugural US$1 billion Limited Recourse Series 4 Capital Notes offering
- A syndicate of underwriters
SECURE Energy Services Inc. in its $300-million high-yield note offering
- First Capital REIT
The agents in connection with First Capital REIT’s offering of $300 million Series B unsecured debentures
- Royal Bank of Canada
Royal Bank of Canada in its $750 million Institutional Preferred Shares Series BU offering.
- The Initial Purchasers
goeasy Ltd. in its closing of an offering of US$550 million senior unsecured notes
- CIBC World Markets
The syndicate of underwriters in the US$2.25 billion bond offering by the Province of British Columbia
- Emera Incorporated
Emera Incorporated in its $500 million senior unsecured note financing
- goeasy Ltd.
The Underwriters in goeasy’s $58 million bought deal offering of common shares
- Mind Medicine
Mind Medicine in its US$30 million public offering
- Lion One Metals Limited
Lion One Metals Limited in its bought deal offering with Eight Capital and Canaccord Genuity Corp.
- Advising Canadian and non-Canadian banks and other corporations in negotiating derivative arrangements (including within the ISDA, GMRA and GMSLA frameworks)
- Advising Canadian public companies on balance sheet and other hedging arrangements
- Advising Canadian tax-exempt investors on the use of derivatives as a substitute for direct investment
- Advising Canadian investment funds and other market participants regarding compliance with tax rules concerning derivative forward agreements, synthetic equity arrangements and synthetic disposition arrangements
- Advising Canadian and international intermediaries on the tax treatment of securities lending transactions with Canadian counterparties and over Canadian securities
- Establishing and restructuring securitization vehicles
Latest Insights
-
Osler Update May 7, 2026
Canada moves ahead with changes to qualified investments for registered plans
Government introduced Bill C-31 that includes previously released proposal to add two new “qualified investment” fund categories.
Read more -
Webinar November 6, 2025
Canadian Tax Law Insights: the 2025 federal budget and its implications for Canadian businesses
Decode the budget with experts from our leading Tax Advisory and Tax Litigation/Disputes teams.
Read more -
Webinar October 13, 2022
Recent Developments in Hybrid Securities
An update on recent developments in hybrid debt, with a particular focus on hybrid debt securities that provide equity credit for rating agency...
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Osler Update December 13, 2021
People, planet and performance: Embracing ESG
In 2021, we witnessed markedly greater attention being paid to Environmental, Social and Governance (ESG) considerations.
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Awards and Recognition
-
Recognized in Tax Law
—Best Lawyers in Canada -
Recognized in Tax
—Legal 500 -
Highly Commended by the Financial Times North American Innovative Lawyers Awards for structuring rating agency hybrid notes issued by Emera Inc. as part of US$ 6.2 billion in concurrent offerings
—Financial Times -
Recognized in Derivative Instruments; Investment Funds & Asset Management – Investment Funds – Tax
—Canadian Legal Lexpert Directory
-
Recognized in General Corporate Tax as a Notable Practitioner
—International Tax Review
Media Mentions
-
Osler News November 14, 2025
Osler recognized as a Tier 1 firm in ITR’s World Tax 2026
Osler has once again earned coveted Tier 1 rankings across all four categories.
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Osler News August 25, 2023
Osler recognized as a Tier 1 firm in ITR’s World Tax Guide 2024
Osler is proud to once again be recognized as a Tier 1 firm in the 2024 edition of the International Tax Review’s World Tax guide. Additionally, 19...
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Media Mentions March 29, 2023
Ottawa’s newest tax hit signals concerning reliance on financial sector for revenue, analysts say – The Globe and Mail
The 2023 federal budget proposed amendments to tax rules on dividends received by Canadian financial institutions. Osler partner Timothy Hughes, Tax,...
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Osler News November 25, 2020
Financial Times shortlists Osler for Innovative Lawyers North America Awards 2020
Osler is pleased to announce the firm has been shortlisted for the Financial Times Innovative Lawyers North America Awards 2020 in the area “The...
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Speaking and Writing
Speaking Engagements
Canadian Tax Law Insights: the 2025 federal budget and its implications for Canadian businesses
Read more- ESG Investing and Financing for Pension Funds
Speaker, September 21, 2021
Credentials
Education
- Oxford University, B.C.L.
- Dalhousie University, LL.B.
- Queen’s University, B.Mus.
Languages
- English
Professional Affiliations
- Ontario Bar Association
- Canadian Tax Foundation
- International Fiscal Association