When professional athletes sign big contracts or executives relocate across borders, the tax implications can be as complex as the game itself. In this episode, Gerry Scott talks with David Silber, Partner at Crowe Silverman LLP, about how athletes and high-income earners structure their finances when moving between Canada and the United States.
David leads the firm’s Sports and Entertainment Division, advising athletes in hockey, baseball, basketball, F1, tennis, golf, and more. He and his team help clients determine tax residency, manage multi-jurisdiction income, and build long-term financial strategies that protect their earnings.
Gerry and David break down:
How tax residency is actually determined
What happens when athletes split their time between two countries
How U.S. and Canadian tax authorities coordinate on cross-border income
The advantages and limitations of RCAs (Retirement Compensation Arrangements)
How state-by-state taxation affects athletes playing in the U.S.
When buying property in Canada helps or hurts an athlete’s tax position
How departure tax works when leaving Canada
Why executives recruited from the U.S. face many of the same planning challenges as pro athletes
David also shares insights into signing bonuses, TFSA restrictions for U.S. residents, and why agents increasingly involve tax professionals before deals are finalized.
Connect with David: https://www.linkedin.com/in/david-silber/
https://www.crowe.com/ca/crowesoberman/about-us/our-people/david-silber
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