Red Sox-Dustin May 2025 Trade Aging Like Total Disaster

The Boston Red Sox will begin a three-game series on Friday night against the St. Louis Cardinals and there will be a familar face on the other side.

Dustin May is scheduled to take the mound for the Cardinals. Boston fans will remember May after he had a cup of coffee with the organization in 2025. Boston, while needing one more starter to make a push to the playoffs, went out and acquired May from the Los Angeles Dodgers in exchange for outfielders James Tibbs III and Zach Ehrhard. At the time, Tibbs was Boston's No. 5 prospect and Ehrhard was the team's No. 27 prospect. May has all of the talent in the world, but the deal was weird at the time.

He had a 4.95 ERA in 19 total appearances, including 18 starts, with the Los Angeles Dodgers before the trade. Boston traded Tibbs, who was acquired in the Rafael Devers trade and Ehrhard, for a rental that didn't work out. May had a 5.40 ERA in six total appearances with Boston. The Red Sox bet on the upside of May but things just simply didn't work out. Now, they will face off against him as a member of the Cardinals on the road.

The Red Sox Will Face Dustin May On Friday Night

Mar 29, 2026; St. Louis, Missouri, USA; St. Louis Cardinals starting pitcher Dustin May (3) looks on as he walks off the field after the second inning against the Tampa Bay Rays at Busch Stadium. Mandatory Credit: Jeff Curry-Imagn Images | Jeff Curry-Imagn Images

If May takes down the Red Sox, that will be brutal. One thing that makes the deal look even worse is how well Tibbs is playing in the Dodgers' organization. He has played in 12 games in Triple-A in the Dodgers' organization this season and has slashed .380/.456/.920 with seven homers and 13 RBIs in 12 games played. That's just ridiculous.

You're not going to hit on every deal. That's obvious. But the trade for May was an absolute miss. FanSided's Robert Murray reported that Tibbs has put himself "firmly in the conversation" to make his big league debut with Los Angeles this season.

May has struggled so far this season with the Cardinals in two starts. He has a 15.95 ERA in two starts. But he has the talent to really turn things around. But he didn't have it for the Red Sox. Plus, the guy the Red Sox gave up for him could play a role for the best team in baseball. It's insane.

For Boston fans, they will see May once again on Friday night and the big topic of the night is going to be "What If?" What if he could've lived up to his massive potential down the stretch for Boston? What if he stayed healthy for the Red Sox? What if the Red Sox didn't trade Tibbs? The list goes on. All in all, it just wasn't Boston's best move.