There next to 0 chance at a pre-free agency extension that's for sure. He'd be an idiot not to go to FA and let teams compete against each other rather than just letting 1 team do it. Even though he's not in Soto's league thus far in his career, if he has a full year like his second half he's gonna get a pile. He's already turned down whatever extension offers the Jays have offered in the past, which I have no idea what dollar value they were in, but... if i had to guess they were in the 200 million range probably pretty early on. Pure speculation on the number of course, but we know they've been talking every offseason since at least 2021.
Vlad's just betting on himself like Soto did. It just remains to be seen how it works out for him.