Good Faith in Contract Law, Supreme Court Advocacy, and the Power of Legal Writing with Brandon Kain

This week on the podcast, I had the privilege of sitting down with Brandon Kain. Brandon is a partner in the litigation group at McCarthy Tétrault LLP in Toronto, an adjunct law professor at the University of Toronto and Western University, and one of Canada's premier appellate litigators. Before entering law school, Brandon completed undergraduate and master's degrees in philosophy. Today, he is counsel on landmark Supreme Court of Canada appeals, including Bhasin v. Hrynew and C.M. Callow Inc. v. Zollinger, and the author of the monumental two-volume treatise Good Faith in Canadian Contract Law, which won first place in the 2025 Walter Owen Book Prize. We got into how studying symbolic logic and philosophy sharpens statutory and contractual interpretation, what practitioners still misunderstand about good faith in contracts, and how he reinvented his own career from a firm research lawyer to a courtroom advocate. What you will learnWhy good faith is a chameleon, not a monolithic duty. Many lawyers talk about good faith as if it is a single, free-floating rule. Brandon explains how the Supreme Court in Bhasin actually established good faith as an underlying organizing principle, and why keeping its boundaries slightly uncertain stops bad actors from gaming the system. Contractual discretion vs. interpretation. Drawing on recent jurisprudence like Wastech and Datastar, Brandon clarifies why the duty to exercise contractual discretion reasonably is not a general principle of interpretation or an objective "reasonable person" test. Instead, reasonableness is strictly anchored to the specific purposes for which the parties granted that discretion in their bargain. The Neil Finkelstein rule of appellate advocacy. When arguing a case that could reshape national law, it is tempting to focus on grand legal theory. Brandon shares a vital lesson from his late mentor Neil Finkelstein: courts exist to resolve concrete disputes between litigants. Your primary job is to show why your client wins on any reasonable version of the law rooted in the facts. Three takeawaysArgue to win for your client, not to rewrite the textbook. Even at the Supreme Court of Canada, judges are focused on deciding concrete disputes. Anchor your appellate arguments in the record and the commercial realities of the parties rather than abstract policy lectures. Treat yourself as a lifelong student of the law. The law is too deep and dynamic to rely solely on what you learned in law school. Read widely across legal history and comparative jurisdictions like England, Australia, and New Zealand to build a broader narrative of how legal doctrines evolve. Invest relentlessly in your legal writing. Clear, rigorous writing is the ultimate differentiator for a young lawyer. Take advantage of continuing education through organizations like The Advocates' Society and read classic books on written advocacy to sharpen your style. Guest: Brandon Kain, Partner at McCarthy Tétrault LLP, appellate litigator, adjunct law professor, and author of Good Faith in Canadian Contract Law. Where to listen and how to support the showSearch Studying Law Around the World on Spotify, Apple Podcasts, or YouTube. If you found value in this episode, please take a moment to follow the show and leave a rating. Selected episodes of Studying Law Around the World are eligible for Continuing Professional Development (CPD) credit with the Law Society of Ontario (LSO) and Continuing Legal Education (CLE/CPD) credit with the Law Society of British Columbia (LSBC). For approved episodes, accreditation details, and participation information, please visit: https://studyinglawaroundtheworld.com/