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 Soberman 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

Spending time in the U.S.? Take the guesswork out of tracking your days. Download the Snowbirds U.S. Day Tracker app to monitor your stays, stay compliant, and avoid costly surprises at the border.