Flash back to 2018 when John Tavares abandoned the New York Islanders and signed a massive seven-year, $77 million deal with the Leafs, complete with a $15.25 million signing bonus. Here's where things get tricky. While Tavares is a Canadian, thanks to his residency at the time of the signing he was still a U.S. taxpayer. Once he moved to Toronto,
the CRA stepped in and claimed he owed them Canadian income taxes on that signing bonus.