Though we’re still a couple weeks away from the start of the postseason, it’s never too early to start talking about the topic that captures our attention every winter: free agency. In this roundtable, MLB.com examines the possibilities for Blue Jays shortstop Bo Bichette, who will enter free agency for the first time this offseason.
Alyson Footer, editor/moderator: The Blue Jays’ focus is solely on their playoff push, but whenever the postseason ends for them – and obviously, with the roll they’re on, it could be a while before their offseason starts – it’ll be back to business. And atop their list of items to address will be Bo Bichette and his free agency. Let’s start with this: How likely is it that he signs a long-term deal with Toronto?
Mark Feinsand, senior national reporter: Bichette has had a big bounce-back season after a poor 2024, setting him up for a big payday this winter. Toronto took care of its top priority earlier this year when Vladimir Guerrero Jr. signed his $500 million deal, making it clear that contending in future seasons is the plan. But will the Jays have enough money to bring Bichette back while also addressing their other holes? Chris Bassitt is a free agent this year, while Kevin Gausman has only one year left on his deal. The guess here is that another team will ultimately offer more money/years, so it will be a matter of whether Bichette wants to stay in Toronto.
Keegan Matheson, Blue Jays beat reporter: Bichette isn't a complicated guy, even though there's been a lot of time wasted trying to get inside his head and analyze his body language. He wants to win and play for an organization that supports that. Right now, the Blue Jays check off both of those. The unspoken part is that he, like anyone else, will want the top contract available to him. Teams are going to have drastically different valuations of Bichette, but no one knows him better than the Blue Jays, and I expect them to be legitimately involved.
They just proved that they're willing to play with the big boys by signing Vladdy to his extension. In doing so, they also showed they're willing to step outside of their rigid projections to land a player who matters. The Blue Jays have the money, have the motivation and have the winning environment. If Bichette wants Toronto, Toronto will want him.
Footer: Things seem to have changed for the Jays from one year ago to now. It wasn't that long ago we were talking about them possibly taking a few steps back, maybe trading away a few of their commodities to trigger a reset. It seemed like they were always the team that were labeled as "disappointing" at the end of the season -- high expectations, subpar product. It's so different now. Would Bichette be swayed just by the simple fact that the Jays are showing an aptitude for putting together a winning roster?
Feinsand: One thing Bichette will have working in his favor this winter is that he’s not only the top shortstop available, but he’s really the ONLY shortstop of note hitting the open market. Alex Bregman is the other notable infielder on the left side (assuming he opts out of his deal with the Red Sox), but if a team wants to make a splash at shortstop, Bichette figures to be their target.
Knowing how to put a winning roster together and committing the funds to do so are two different things. Replacing Chris Bassitt (and eventually Kevin Gausman) will cost money. Vlad is locked in for a long time at a big number. Will ownership be willing to push the payroll to levels it hasn’t been before? I’m guessing these are questions Bichette and his agent will be asking.
But the fact that the Blue Jays are winning -- and that Bichette will see first-hand in October how baseball-crazy that city can be when things are going well -- should help their case.
Matheson: It's rare anything else matters more than money, but Bichette is an obsessive competitor. I don't think he'd have any interest in going through a retool, whether that's in Toronto or elsewhere. If the Blue Jays were dragging out an uneventful, .500 season like many had expected (myself included), I don't think this would even be a conversation worth having. Bichette still hasn't won a postseason game. Wherever he signs, he'll need a shot at that.
Feinsand: One more thing on the shortstop issue….
Matheson: Is he one?
Feinsand: There’s a question within the industry of just how long Bichette will stay at shortstop. Although his bat has rebounded this season, his defense hasn’t been what it once was. I’m not a huge believer in defensive metrics to tell the whole story, but he’s a -13 in Outs Above Average. You don’t have to be Sarah Langs or Mike Petriello to know that’s not great.
We may be looking at a future third baseman or second baseman. That will likely impact the type of contracts teams are willing to present to Bichette this offseason. He’s going to get paid -- and paid handsomely. But I don’t know if we’re looking at the $300 million type of deal Corey Seager got from the Rangers.
Matheson: That's where I think the gap will develop between teams who love Bichette... and teams who think he belongs at second base or third. Granted, the eye test doesn't look as ugly as the numbers because Bichette makes most of the routine plays, but teams looking to sign Bichette need to consider how he'll look at 29, 32 and 35 years old. His sprint speed is declining, too. This could really impact which tier of contract we end up talking about. If there are five teams with genuine interest in Bichette, I think that the gap between Offer No. 1 and Offer No. 5 could be... a lot.
Footer: We know he’s close with Vlad Jr., who just signed a mega-extension. I’m wondering if there would be a desire on Bo’s part to also sign long-term and keep the band together, so to speak, and sort of cement themselves as one of the more important duos in Jays history. How much will his legacy matter to him? If he leaves for another team, the shine comes off a little bit.
Matheson: That's real. They've been close friends and running mates going back to the low levels of the Minor Leagues. What Vladdy represents matters, too, which is a complete commitment to spending and competing.
That said, a few million dollars extra could be enough to convince me to live in another city and Facetime my friends instead.
Feinsand: If all offers are the same, I think there’s something to be said for staying with the only team he’s played for and riding it out with his buddy Vlad. But these things almost always come down to money, and there’s no reason to expect this one will be any different.
Footer: It's interesting that he’ll be a top free agent, but we don't even know what position he's destined for. So if not the Jays, what other teams might be in the market for him? Will they view him as a shortstop?
Feinsand: I think some teams will view him as a shortstop in the near-term, with the idea of potentially moving to second or third at some point. The Tigers make a lot of sense to me; a young, up-and-coming team with payroll flexibility, a terrific manager and a division that should be winnable for the foreseeable future.
The Braves are another team that makes sense baseball-wise, though I don’t know if Atlanta will want to pay the kind of money it will take to sign Bichette.
Matheson: I agree with the Tigers being a threat here. Position is going to determine the field -- or perhaps even expand it -- but I'd roll the Yankees in, too. Even if he's signed as a 2B or 3B, Bichette is a bat that fits in any lineup.
Feinsand: Of course, I never discount the Dodgers and Yankees as potential landing spots, either. Mookie Betts could slide back into the outfield to open up shortstop in L.A., and the Anthony Volpe era could be ending as we speak.
The Yankees have second base (Jazz Chisholm Jr.) and third base (Ryan McMahon) locked up for the next year or two, so they would have to view Bichette as a shortstop for 2026 and figure it out after that.
But if there’s one team I see as the biggest threat to the Blue Jays, it’s the Tigers. They’ve tried to spend money recently, and even though they’re going to have to give Tarik Skubal a big bag of cash soon, there’s plenty of payroll flexibility to sign Bichette if they choose to make a run at him.
Footer: This could be quite a defining October for Bichette, assuming he recovers from his knee sprain. How critical is a strong performance in the postseason?
Feinsand: It’s huge. Missing the final weeks of the regular season isn’t ideal for a free agent, but posting a memorable October can wash all of that away. Bichette hasn’t had many chances to show his stuff on the big stage (six games in total), but he’ll get that next month. Good players get paid. Good players who crush it in the postseason get paid more.
Matheson: It's big. He's played in six postseason games and the Blue Jays have gone 0-6 in those. When you're signing a deal in the hundreds of millions, you're being brought in to win games in October, not June. I think Bichette is built to have a big moment if he comes back from this left knee sprain in time to be part of the postseason run, but that's still a huge variable here. As long as he hasn't already played his final game in a Blue Jays uniform, though, he needs to do this in front of a national (American) audience.
Footer: So, in conclusion… what we have is a talented-but-flawed, soon-to-be free agent who will give us lots to argue about as soon as the World Series is over.
Matheson: I think Bichette will end up being the most debated free agent this winter. It's easy to dream on his offensive upside, but just as easy to poke holes in his defensive game and positional fit. Everyone agreed that Guerrero Jr. was really good... it was just a matter of money. Bichette is going to draw far more debate, and feels like a player whose market could really stretch into the winter.
Feinsand: Bichette may be the most intriguing free agent of the winter for me. The other top guys -- Kyle Tucker, Kyle Schwarber, Bregman -- are who they are. There isn’t much of a question as to what a team will get from them. Bichette had the worst season of his career in 2024, and while he’s bounced back offensively this year, will teams be willing to roll the dice on a six-, seven- or eight-year commitment to him given how recently he struggled? Cody Bellinger -- another potential free agent this offseason -- had a similar situation after leaving the Dodgers, and while he’s done quite well for himself on an Average Annual Value level, he still hasn’t been able to score that big long-term deal. I’m fascinated to see how the Bichette saga plays out.