Timothy Hughes

Timothy 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

  • First Capital REIT

    The agents in connection with First Capital REIT’s offering of $300 million Series B unsecured debentures

  • 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

  • Tantalus Systems

    Tantalus Systems in its inaugural $50 million Shelf Prospectus and related Public Offering

  • RBC Capital Markets, LLC

    The syndicate of underwriters in the US$2.50 billion bond offering by the Province of British Columbia

  • The Syndicate of Agents

    The Syndicate of agents in TELUS Corporation’s $750 million inaugural Sustainability-Linked Bond offering

  • Dream Industrial REIT

    Dream Industrial REIT in its $800 million debenture offering and inaugural green bond issuance

  • Dream Industrial REIT

    Dream Industrial REIT in its $850 million European logistics portfolio acquisition and associated financing

  • Tantalus Systems Holding

    Tantalus Systems Holding Inc. in its $90 million Qualifying Transaction with RiseTech Capital Corp., concurrent financing and graduation to the Toronto Stock Exchange

  • Laurentian Bank

    Laurentian Bank in its inaugural LRCN 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

  • 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 purpos...

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    Recent Developments in Hybrid Securities
  • 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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    People, planet and performance: Embracing ESG
  • 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 by the...

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    ESG investing and financing for pension funds – GPFA webinar
  • 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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View all Insights

Awards and Recognition

  • Best Lawyers in Canada: Recognized in Tax Law
  • Legal 500: Recognized in Tax
  • Financial Times: 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

Media Mentions

  • 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 of...

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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 Pract...

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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 ef...

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View all

Speaking and Writing

Speaking Engagements

speaker 26/11/2023
Canadian Tax Foundation 75th Annual Conference
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speaker 13/10/2022
Recent Developments in Hybrid Securities
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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