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 sits on the Osler Partnership Board and is Chair of the Firm’s UK Desk.
Representative Work
- 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
- 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.
- TELUS Corporation
The Syndicate of agents in TELUS Corporation’s $2 billion three-tranche note offering
- Heritage Mining Ltd.
Heritage Mining in its initial public offering and listing on the Canadian Securities Exchange
- Mind Medicine
MindMed in its US$100 million At-the-Market Program
- The Underwriters
The Underwriters in connection with TELUS Corporation’s US$900 million Sustainability-Linked Bond offering
- Enbridge Inc.
The Underwriters in Enbridge Inc.’s US$1.5 billion offering of notes
- Royal Bank of Canada
Royal Bank of Canada in its $750 million inaugural institutional Preferred Shares Series BT offering
- Hardwoods Distribution Inc.
Hardwoods Distribution Inc. in its $100.6 million offering
- Q4 Inc.
Q4 Inc. in its IPO on the TSX
- Greater Toronto Airports Authority
Greater Toronto Airports Authority in its $400 million offering
- The Underwriters
The Underwriters in Enbridge Inc.’s US$1.5 billion public offering
- The syndicate of agents
The syndicate of agents in Nissan Canada’s $500 million notes offering
- 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
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.
The agents in connection with a $700-million offering of senior notes by Fairfax Financial Holdings Limited
Tenaz Energy Corp. in its inaugural $140-million senior unsecured notes offering
Royal Bank of Canada in its $600 million Institutional Preferred Shares Series BW offering
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.
- TELUS Corporation
The Syndicate of agents in TELUS Corporation’s $2 billion three-tranche note offering
- Heritage Mining Ltd.
Heritage Mining in its initial public offering and listing on the Canadian Securities Exchange
- Mind Medicine
MindMed in its US$100 million At-the-Market Program
- The Underwriters
The Underwriters in connection with TELUS Corporation’s US$900 million Sustainability-Linked Bond offering
- Enbridge Inc.
The Underwriters in Enbridge Inc.’s US$1.5 billion offering of notes
- Royal Bank of Canada
Royal Bank of Canada in its $750 million inaugural institutional Preferred Shares Series BT offering
- Hardwoods Distribution Inc.
Hardwoods Distribution Inc. in its $100.6 million offering
- Q4 Inc.
Q4 Inc. in its IPO on the TSX
- Greater Toronto Airports Authority
Greater Toronto Airports Authority in its $400 million offering
- The Underwriters
The Underwriters in Enbridge Inc.’s US$1.5 billion public offering
- The syndicate of agents
The syndicate of agents in Nissan Canada’s $500 million notes offering
- 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
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Webinar Oct 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 Dec 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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Osler Update Sep 21, 2021
ESG investing and financing for pension funds – GPFA webinar
“It just makes too much sense for both issuers and investors.” Osler’s Timothy Hughes and Michael Innes joined an international panel presented...
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Osler Update Dec 8, 2020
Novel hybrid debt issuances by Canadian banks
Hybrid debt is debt with embedded equity features that are added to meet requirements imposed by a regulator, rating agency or some other third party...
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Awards and Recognition
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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
Media Mentions
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Osler News Aug 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 Mar 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 Nov 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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Osler News Jul 29, 2020
Updated: Osler partners with new Global Peer Financing Association
Osler is proud to support the Global Peer Financing Association, a new association recently formed by a group of beneficial owners to create a more...
Read more
Speaking and Writing
Speaking Engagements
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