Simon's career as a litigator spans a wide array of complex commercial disputes, especially within the realms of shareholder, securities, and privacy litigation. His proficiency has led him to advocate on behalf of clients across all judicial levels in Ontario, including the Supreme Court of Canada, as well as before various regulatory entities. Simon's adeptness at navigating internal, regulatory, and police investigations has solidified his status as a trusted advisor in the legal landscape.

Before his tenure at Osler, Simon honed his skills at another premier law firm, bringing a wealth of knowledge and experience to his current role. A graduate of the University of Toronto's law program, Simon distinguished himself academically by earning the Edward J. Kowal ’65 prize for his achievements in commercial law, along with accolades in Administrative Law, Bankruptcy and Insolvency, Business Organizations, and Advanced Business Law. His participation in and contributions to mooting at the university level, including coaching and winning the Corporate and Securities Law Moot, underscore his passion for legal advocacy.

Simon's pre-law career in the technology sector as a database and web developer provides him with a unique perspective on the tech industry's legal challenges. This background, combined with his undergraduate accolades in debating, including winning the North American Debating Championships, showcases his exceptional argumentation and analytical skills.

Among the noteworthy cases Simon has been involved in are his representation of the successful respondent in a landmark Supreme Court of Canada case on crown copyright, and his role as counsel to an intervenor in pivotal cases regarding Ontario’s Anti-SLAPP provisions. His work extends to defending an international mining company, assisting a Canadian technology firm in arbitration matters, advising a Canadian cannabis company through various legal hurdles, and representing a medical device manufacturer in a significant decision on third-party litigation funding.

Simon's contributions to the legal community are further evidenced by his recognition and the accolades he has received, marking him as a distinguished litigator within Osler's ranks. His affiliations with The Advocates’ Society and the Canadian Bar Association are testaments to his active engagement and commitment to the legal profession.