The Boston Red Sox attempted a big swing at the 2025 trade deadline, as they hoped to land Minnesota Twins pitcher Joe Ryan to help carry them through the postseason and beyond as their No. 2 starter.

The Twins didn’t accept any of the Red Sox’s significant trade offers, and they were forced to turn to the Los Angeles Dodgers to trade for Dustin May. But hours before, the Toronto Blue Jays made the deal Boston should’ve done.

The Blue Jays traded for longtime Cleveland Guardians pitcher Shane Bieber at the trade deadline, despite his injured list status. Bieber underwent Tommy John surgery just weeks into the 2024 season, and his recovery took over a year. Toronto’s risk has paid off.

Bieber debuted on August 22 and posted a 3.57 ERA, a 1.02 WHIP, 37 strikeouts and seven walks over 40.1 innings in the regular season. He’s carried his dominance into the postseason, where he’s also clocked a 3.57 ERA with 18 strikeouts and six walks over four starts. He made possibly the start of his life on October 28 when he held the Dodgers’ usually gritty offense to one run on four hits in Game 4 of the World Series.

Red Sox were interested in trading for Blue Jays starter Shane Bieber, who stunned Dodgers in World Series Game 4, at the deadline

Bieber’s recovery from Tommy John surgery has gone smoother than many other pitchers who have undergone the same procedure, which the Blue Jays, Red Sox and Guardians couldn’t have anticipated before the trade deadline move. It was equally risky for Boston to pursue May, who had never pitched more than 56 innings in a single season before 2025.

Embed X: https://twitter.com/MLB/status/1983339552963211522/video/1

Not only did May’s stats not jump off the page, the Red Sox seriously overpaid the Dodgers for him — as they tend to do in their exchanges with this specific club. May clocked a 5.40 ERA and a 1.694 WHIP in the 28.1 innings he pitched with the Sox. He also fell injured with elbow neuritis in early September and was not available for the postseason. Boston’s pitching depth was severely depleted by October, with May, Lucas Giolito, Richard Fitts, Hunter Dobbins, Tanner Houck, Kutter Crawford and Patrick Sandoval all on the IL.

The Red Sox were among the few teams interested in signing Bieber before the 2025 season while he recovered from surgery, a strategy which has become their specialty in recent seasons (even though it doesn’t always work out). Had they made the move before the Jays did, maybe their playoff run would’ve lasted longer than the Wild Card round.