3 free agent deals already made this offseason we wish the Blue Jays had signed

The Toronto Blue Jays likely have no regrets so far this offseason after being proactive in the free agent market to retool their roster ahead of the 2026 MLB season. With key additions in Dylan Cease, Cody Ponce, Tyler Rogers and Kazuma Okamoto via free agency, the Blue Jays were able to gain valuable assets to help the organization without giving up any in return.

However, as much as the great work that has been done thus far by Toronto this winter, there were a few free agent targets that the Blue Jays might have let slip through that could have had a huge impact on the team going forward had they been successful in recruiting them.

3 free agent deals already made this offseason we wish the Blue Jays had made 

Pete Alonso

With the Blue Jays craving for an elite power bat to inject into their lineup for the past few years, Pete Alonso would have provided that exact solution had he landed with Toronto instead of their arch divisional rivals in the Baltimore Orioles. With the ability to consistently put up 35-plus home runs and 100-plus RBIs per season, he would have instantly transformed the Blue Jays into an offensive powerhouse.

Paired with Vladimir Guerrero Jr., we could have had one of the best power-hitting duos of this generation playing on the same team. More impressively, Alonso has been as durable as one could be, having played all 162 games on the schedule for the past two seasons and at least 152 games every year (not including the COVID-shortened 2020 season) since joining the league in 2019.

Sure, one would have debated about how he would have fitted in positionally given that he is a first baseman by trade, which happens to also be Guerrero’s main position. But to be able to add a player of Alonso’s power and calibre, you do everything you can to find a way to make it work. After all, Guerrero did mention once before that he was willing to change positions if a move would make the Blue Jays better. Instead, the Blue Jays will now be forced to face him for years to come in the ultra-competitive AL East division.

Edwin Diaz

For any legitimate contender, having a shutdown reliever is vital for long-term success. There are so many close games over the course of a 162-game schedule, and having it come down to the closer to finish off tight ballgames can significantly shift the balance between the team's win and loss column. As a result, the Blue Jays totally missed out on the opportunity to add the electric Edwin Diaz to their relief corps.

Not to say that Jeff Hoffman can never become that shutdown closer for the Blue Jays, but with Diaz, you would get a proven, consistent sure thing from here on out. After all, the 31-year-old right-hander had posted 253 career saves with a 2.82 ERA, 1.04 WHIP, along with a 839 strikeouts in just 519.1 total innings pitched over his nine seasons in the majors.

Diaz was also coming off one of his best seasons of his career in 2025 with the New York Mets in which he compiled a 1.63 ERA, 0.87 WHIP, with 98 strikeouts in 66.1 innings pitched over 62 appearances. 

In the worst possible case scenario, Diaz has now joined the reigning World Series champions Los Angeles Dodgers. In doing so, it will make the task of dethroning the champs that much more difficult for the Blue Jays, or anyone else. 

Alex Bregman 

While Toronto and all of Jays nation have been busily focusing their attention on the potential reunion with star shortstop Bo Bichette, they had inadvertently let a true difference maker fall through the cracks as Alex Bregman signs with the Chicago Cubs. As a former three-time All-Star, two-time World Series champion and AL MVP finalist in 2019, Bregman has the ability to put up 20-plus home runs and 100-plus RBIs on a yearly basis while maintaining a solid batting average above .270 and OPS above .800.

He would have been an ideal replacement for Bichette in the Blue Jays infield not only from an offensive standpoint, but defensively as well as a former Gold Glove winner. More importantly, with the modest five-year deal that he signed with the Cubs, Bregman would have provided the Blue Jays with the “Bichette-level” type of production but on a much shorter term commitment.

That could have given Toronto some much-needed financial flexibility while adding a proven winner to help inspire and lead the ballclub to get the job done in the near future. Unfortunately, now with Bregman also off the board, the demands for top free agents such as Bichette and Kyle Tucker will likely skyrocket, making the chances of the Blue Jays securing one more high profile player this winter that much more improbable.