How Vladimir Guerrero Jr. status affects Blue Jays’ offseason

This story was excerpted from Keegan Matheson’s Blue Jays Beat newsletter. To read the full newsletter, click here. And 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.

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:

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…