U.S. Cross-Border Legal Services: Overview

Many of our clients are pursuing business strategies that cross the Canada/United States border. To meet their needs, Osler has developed a depth of expertise in the key areas of U.S. business law most in demand by our clients, including corporate law, tax, mergers & acquisitions, corporate finance, financial services, corporate governance, executive compensation, and  pensions & benefits law.

Integrating our Canadian and U.S. business law services, we believe, gives our clients a significant advantage, because they can now receive business critical U.S. legal services from Osler more effectively and more efficiently. Where laws and practices differ between the two countries, we provide integrated cross-border legal counsel rather than leaving our clients with the challenge of reconciling advice from separate firms on either side of the border.  Where laws and practices are the same, we do the necessary legal work once.  That reduces expense and potential delays for our clients.

Overall, clients get better integrated U.S. and Canadian legal advice at a lower cost from Osler than when they retain U.S. and Canadian law firms. 

Mergers & Acquisitions

Osler’s reputation in mergers and acquisitions in Canada is firmly established.  We have had a key advisory role in many of the most important M&A transactions announced or completed over the past decade.  In independent rankings, Osler has been placed first among Canadian law firms for transactions within Canada, across the U.S. border, and for transactions with international involvement.

Our firm has extended the breadth of service for M&A transactions to the United States, where we help our clients with acquiring and selling U.S. and Canadian entities, acquiring minority investments and entering into joint ventures, including providing advice on U.S. securities laws, Delaware and New York corporate laws, and stock exchange regulations.

Osler’s U.S.-based lawyers have advised on public tender offers, private acquisitions and divestitures, and “going private” transactions.  We also counsel clients on their disclosure obligations under U.S. federal securities laws in connection with their acquisitions and dispositions. Our work regularly includes discussions with representatives of the U.S. Securities and Exchange Commission, stock exchanges and financial advisors.

Corporate Finance & Securities

We regularly advise public and private companies and investment banks in a broad range of securities offerings, including debt and equity offerings under the Multi-jurisdictional Disclosure System (MJDS), initial public offerings (IPOs), investment-grade and high-yield debt offerings (both SEC-registered and under Rule 144A/Regulation S), shelf registrations, secondary offerings and Regulation D/Section 4(2) private placements.  

Our work includes providing advice on restructuring companies in advance of IPOs, negotiating terms of complex securities, including preferred stock, convertible debt and warrants, and covenant packages in high-yield debt securities, drafting prospectuses/offering circulars, negotiating underwriting agreements, indenture/fiscal agency agreements and conducting due diligence. 

We also regularly counsel public companies and their stockholders on reporting and disclosure requirements under the U.S. federal securities laws, proxy solicitations, stock exchange compliance matters and Sarbanes-Oxley compliance.  Our lawyers are also experienced with debt and equity tender offers and exchange offers, "going private" transactions and rights offerings.

Corporate Law and Corporate Governance

Corporate governance is of vital importance to clients and their stakeholders – from directors and executives to employees, investors and regulatory authorities.  Drawing on our experience on both sides of the border, Osler advises clients on both Canadian and U.S. corporate law and corporate governance requirements.  We also offer practical insights into how changes to corporate law and corporate governance rules and enforcement, as well as investor expectations, will affect our clients’ business strategies.


The success of a business, a transaction, or a new venture can depend on the quality of the tax advice provided. Osler’s Tax Department is an historical strength of the firm and is consistently ranked in the top tier of tax advisors among Canadian law firms. Some of Canada’s largest multinational corporations are among our clients and we are at the heart of most innovative international transactions involving Canadian entities.  The group includes leading experts in the taxation of mergers & acquisitions, general taxation advisory matters, tax litigation and dispute resolution and cross-border taxation.

We provide U.S. federal tax advice on a broad range of activities, including taxable and tax-free acquisitions, spin-offs and financings. This combined experience and expertise in both countries means that Osler can provide fully integrated, high-quality strategic and practical tax advice to meet our clients’ needs.

Financial Services

Osler’s Financial Services Group advises some of North America’s leading financial institutions and corporate borrowers on a wide variety of U.S. and cross-border debt financing transactions.  These include syndicated secured and unsecured credit facilities, acquisition finance facilities, leveraged finance transactions (such as second lien financings in the context of leveraged buyouts), subordinated debt financings, commercial and asset-based lending, private placements, swaps, and structured finance transactions. 

Executive Compensation, Pensions & Benefits

Executive compensation and pensions and benefits are under significant regulatory and investor scrutiny. Osler offers practical business-focused advice to clients on structuring their executive compensation arrangements, including share-based incentive programs; deferred compensation plans (Code Section 409A compliance); employment agreements and severance agreements, particularly in an M&A context.  We also assist clients with the establishment and maintenance of U.S. tax-qualified retirement plans, welfare benefit plans and related trusts that are subject to the Employee Retirement Income Security Act (ERISA) and the U.S. Internal Revenue Code.

For multinational clients who move executives across the border, Osler’s experts in both Canada and the United States work seamlessly together to structure efficient and effective executive compensation programs.