Looming money question could dash Blue Jays' dream of Vladimir Guerrero Jr. extension

The Toronto Blue Jays have, slowly but surely, started to salvage what was shaping up to be a disastrous offseason. Andres Gimenez helps stabilize the infield picture. Anthony Santander isn't Juan Soto, but he is the sort of powerful corner outfield bat that the team has needed for years. And Max Scherzer helps fill out nicely a rotation that seemed exactly one arm short just a few days ago.

But while Ross Atkins has helped stop the bleeding a bit, the most important question of all still looms: Will the Jays be able to sign Vladimir Guerrero Jr. to a long-term extension before the start of spring training in a couple of weeks, or will they lose their foundational star in free agency next winter? Toronto clearly hasn't given up hope yet, as talks between the two sides continue. But they could be facing quite the financial Catch 22 here, as Guerrero Jr.'s asking price and the moves that convince him to stick around threaten to take them into rarefied air.

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Could luxury tax crunch keep Blue Jays from keeping Vladimir Guerrero Jr.?

If Guerrero Jr. does opt to forgo free agency, he's going to do so for well over $400 million total — and over $30 million per year. That's just the cost of doing business for a 26-year-old superstar just entering his prime. But while we know that Jays ownership does have that kind of cash — they went up to $700 million over 15 years for Juan Soto, remember — it carries some thorny ramifications for the team's future.

After adding Gimenez, Santander and Scherzer this offseason, Toronto's luxury tax number sits at around $273 million — around $28 million below the highest luxury-tax threshold of $301 million. Crossing that threshold comes with significant penalties, the main reason why the team has never done it before. But if they want to both lock up Guerrero Jr. and continue to add pieces around him — pieces like, say, Alex Bregman or Pete Alonso — then suddenly the math gets dicey, even with several contracts (Bo Bichette, most likely, in addition to Chris Bassitt) coming off the books in a year's time.

And it's hard to imagine Guerrero Jr. signing on for the next decade-plus without some more assurances that the team around him will be good enough to get him to the postseason regularly. Given the Blue Jays' depth chart right now, that would almost certainly mean landing Bregman, assuming the third baseman is willing to come to Canada. Adding, say, $55-60 million more to the books, however, could run the payroll into a place it's never gone before — and a place that the Rogers family has never shown it has the stomach for.

For Guerrero Jr., you'd have to think they'd be willing, at least for one year. But spending into the Cohen tax means an 80 percent tax on every additional dollar spent, in addition to draft order penalties. That's a heavy price, one that will test this regime's commitment to truly competing in Toronto.