When the Blue Jays signed All-Star slugger Vladimir Guerrero Jr. to a 14-year, $500 million contract extension in April, the news was met with some mixed responses from the general baseball public.

Here was a homegrown star, a born Canadian who, with just one year left until free agency and after a lengthy and at times testy negotiation process , was pledging to spend the rest of his career in Toronto. For an MVP-caliber player entering his age-26 season, it was the kind of day that organizations dream about.

Except there was a way to view the decision as a desperation move, one made by a gambler who’s barely hanging onto their seat at the table deciding to push a dwindling chip stack all in. The Jays were coming off of a last-place finish that followed three playoff runs in four

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