This offseason, the Toronto Blue Jays have been looking for ways to bolster their roster heading into 2026. So far, they have made their biggest splashes in the free agent market, landing elite starter Dylan Cease and recruiting KBO star Cody Ponce within a week’s time.
However, the Blue Jays shouldn’t take their foot off the pedal just yet as their division rivals could counter with their own big moves to match or even outdo Toronto. Ex-MLB GM Jim Bowden of The Athletic has recently posted some hypothetical trades that he would like to see (subscription required) at the Winter Meetings. Bowden has some of Toronto’s division rivals getting massive impactful players via the trade route to significantly improve their roster for the upcoming season.
Ex-MLB GM has Blue Jays rivals getting everybody in these wild trade proposals
For the New York Yankees, Bowden has them acquiring top arms Freddy Peralta and former Cy Young winner Sandy Alcantara to bolster their starting rotation which would already have Gerrit Cole, Carlos Rodon and Max Fried to begin with.
That means they could have five potential number one starters pitching for them in 2026, which would be a nightmare for the Blue Jays and just about everyone else in the division. To top it off, Bowden even has three-time All-Star and former MVP finalist Ketel Marte joining New York as well in exchange for two top prospects to give them an offensive boost. If that somehow comes true, it might mean we will be seeing a lot of Yankees and Los Angeles Dodgers World Series matchups.
Jim Bowden was on one today:https://t.co/xVAxSI78OO pic.twitter.com/a5W2fKFX9d
— Bleacher Creatures (@The_Bleacherss) December 5, 2025
But the Yankees aren’t the only one to benefit from Bowden’s wild trades, as the Boston Red Sox will land another ace to team up with Garrett Crochet and Sonny Gray. The Red Sox would be getting Hunter Greene from the Cincinnati Reds for Jarren Duran, Payton Tolle and Jedixson Paez. In doing so, both the Yankees and Red Sox would have improved their rotation enough that it would be comparable or perhaps even better than what the Blue Jays have formed so far this offseason.
To top it off, Bowden also has a trade involving the Tampa Bay Rays that would net them three young pitchers and a promising catcher in Ethan Salas at the expense of Drew Rasmussen and Shane Baz. With the way that the Rays usually get the most out of their young pitchers with their development system, they could suddenly be back in contention in no time once they reach their potential.
Surprisingly, Bowden doesn’t have any trades involving the Blue Jays. That could be due to the fact that their most coveted prospects in Trey Yesavage and JoJo Parker are likely off-limits in trade talks, leaving it a little harder for Toronto to formulate a blockbuster move as a result.
Nevertheless, with the Blue Jays having the slightly early jump on everyone else in their division, they will need to hold them off with another big move or two to complete the offseason to deem it successful when the dust settles.
