Toronto's future hinges on this offseason -- and its biggest star

This story was excerpted from Keegan Matheson’s Blue Jays Beat newsletter. Subscribe to get it regularly in your inbox.

TORONTO -- The next two months should tell us who the Blue Jays are. Not just for 2025, but beyond that.

There’s a sense of urgency to this offseason -- overdue, many would argue -- but we’re back to having the conversation about competitive windows for this organization. Each of the next two winters hold the possibility of those windows slamming shut, but that doesn’t need to happen. For a club spending at Toronto’s level, at least, it never should.

First, let’s frame what all of this means. Many of the Blue Jays’ biggest names see their deals expiring following either the 2025 or ‘26 seasons, including:

Expiring after 2025: 1B Vladimir Guerrero Jr., SS Bo Bichette, RHP Chris Bassitt, RHP Chad Green, RHP Erik Swanson

Expiring after 2026: RHP Kevin Gausman, OF George Springer, OF Daulton Varsho, C Alejandro Kirk (Note: RHP José Berríos may opt out of the final two years of his contract after 2026)

It was easier for this organization to stomach the letdowns of 2020-23, as they were still adding and still had the bulk of these large contracts ahead of them, but there are plenty of expiry dates creeping up at the same time now, and the Blue Jays don’t have a single recent postseason win to show for it. They’re spending to a level that fans in this market have begged for, particularly from an ownership group that’s long been capable of doing so, but the results haven’t followed when it matters most.

For that window to stay open, this feels like the offseason something has to happen. This conversation, like almost any other, circles back to Vladimir Guerrero Jr.

Vladdy is the face of the franchise again, the prodigy who has once again made good on all of the hype. Indirect as Guerrero’s path has been, he’s proven himself to be a player worthy of a mega deal. Think something in the range of these names:

Rafael Devers: 10 years, $313.5 million
Bryce Harper: 13 years, $330 million
Corey Seager: 10 years, $325 million
Manny Machado: 10 years, $300 million
Xander Bogaerts: 11 years, $280 million

Guerrero can be a difficult player to find a comp for given his position, but this is the range Guerrero could land in and those are the names he’ll be compared to from a broader standpoint of value. We can argue a few million dollars in either direction, but at that price tag, it’s a drop in the bucket. Guerrero is going to cash in, whether it’s in Toronto or somewhere else.

Extending Guerrero this offseason would essentially guarantee that the Blue Jays will continue to spend into 2026, ‘27 and beyond. In that world, if a star like Gausman or Bichette left in free agency, they’d be replaced aggressively. In a world without Guerrero -- or another long-term splash like Corbin Burnes or Max Fried -- then the worry creeps in that the Blue Jays could use those ‘26 and ‘27 seasons to pivot, retool, rebuild, whichever buzzword you’d like to attach to it.

The passing of time doesn’t exactly make optimism grow, either.

Soon enough, Juan Soto will sign a monstrous deal. Yes, the Blue Jays are serious about taking a run at Soto, but they’re up against the free-wheeling Steve Cohen and the Mets, the pride of the Yankees and the seemingly rekindled spirit of the Red Sox. It’s not impossible, but good luck. When we add Soto’s deal, which should top $500 million and could top $600 million, alongside Shohei Ohtani’s $700 million deal from a year ago, it’s clear MLB contracts are beginning to soar for the right stars.

Guerrero is neither of the men mentioned above, but he’ll be hitting free agency at 26, still with both feet planted in his prime. Unless the Blue Jays are offering him the world, Guerrero has every reason to play this out and open up an incredible bidding war this time next year. It’s a dangerous, dangerous game for Toronto to play.

Soto’s pursuit is the shiny new story, but it all comes back to Guerrero, and that will only intensify next week when the MLB Winter Meetings descend on Dallas. Are the Blue Jays trying to run this back one more time, then figure out 2026 when ‘26 comes? Or can this organization turn the past few years of budget into Toronto’s new norm, sitting at a table with baseball’s powerhouses for the next decade?

The answer, as it has all along, may still lie with Vladimir Guerrero Jr.