Blue Jays Still Have Massive Looming Question Heading into Winter Meetings

What is the biggest question for the Toronto Blue Jays heading into the Winter Meetings?

Oct 24, 2025; Toronto, Ontario, CAN; Toronto Blue Jays executive vice president and general manager Ross Atkins speaks to the media before game one of the 2025 MLB World Series against the Los Angeles Dodgers at Rogers Centre. | Nick Turchiaro-Imagn Images

With the winter meetings right around the corner, the Toronto Blue Jays have been very active so far, but there is still work to be done. 

Coming off just barely losing the World Series, the Blue Jays have come into the offseason on a mission to improve. This was a team that could have beaten the Los Angeles Dodgers this year, but now they are really going all-in. 

Even though the team has had trouble in the past recruiting top free agents, that is no longer the case. As a World Series contender with a plethora of financial assets, Toronto is a desirable destination. So far this winter, they have been able to land a couple of notable pitchers to further improve their starting rotation. 

With both Dylan Cease and Cody Ponce signing, the rotation for the Blue Jays looks fantastic on paper. Now, the attention will be turning to the lineup along with the bullpen, and the team still has a looming question. 

MLB.com recently wrote about the top question for the Blue Jays this winter being whether or not they will be bringing back star shortstop Bo Bichette. 

Bringing Back Bichette is a Massive Decision

John E. Sokolowski-Imagn Images

While the contract numbers don’t seem to be an issue for Toronto in their pursuit of Bichette, the team appears to also be interested in signing star outfielder Kyle Tucker. More than likely, it would have to be one or the other, and the case can be made that Tucker is a better fit. 

Even though Bichette has had a lot of success with the Blue Jays and is a homegrown talent, coming up in the farm system with Vladimir Guerrero Jr., he’s not the same player as Tucker. The star outfielder is the top prize in free agency this winter and does everything well. 

While Tucker did have a tough stretch when he was playing injured in 2025 with the Chicago Cubs, he still put together a remarkable season. For Bichette, he played excellently as well, but there are some concerns about his defensive abilities at the shortstop position going forward. 

When comparing the two, Tucker is the better all-around player, but he could cost the team at least $100 million more over the course of a contract. With the Blue Jays already spending a lot of money this winter, it will be interesting to see if there is a number that is too high for them. 

While the team decides which option is better, they do have to make sure that they get at least one of the sluggers. Even though they have improved the rotation dramatically this winter, Guerrero needs a sidekick in the lineup.