Could Vlad's Enormous Signing Bonus Be A Massive Tax Guerr-Error?

When the worlds of tax and baseball collide, I always find myself immersed in the intersection, considering the tax consequences while also making sense of the baseball implications. The details of Vladmir Guerrero Jr.'s new US$500 million contract extension with the Toronto Blue Jays has sparked much conversation both on and off the field.

According to reports, a staggering US$325 million of Guerrero's US$500 million contract extension with the Blue Jays is in the form of a signing bonus, payable over the duration of the contract. The balance of the contract, US$175 million, will be paid as salary over the course of the 14 years of the contract extension. In Canada, the distinction between the taxation of a signing bonus and the taxation of salary, particularly for a non-resident like Guerrero (who resides in Florida, which, notably, has no state taxes), is of great consequence.