Top 5 Ex-Red Sox Making Boston Regret Cutting Them Loose

If it feels like this season has brought an inordinate string of bad publicity for the Boston Red Sox, that probably has something to do with more than the team struggling on the field.

Decisions the Red Sox have made over several years, some during Craig Breslow's tenure as chief baseball officer and some before, are coming back to haunt them. All around the league, former Red Sox players are having great seasons that Boston could sorely use.

In no particular order, here are the five old friends causing the most pain to view from afar.

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Kyle Schwarber - PHI DH

You won't even find Rafael Devers on this list, even as Boston's designated hitter from this time last year has gone ballistic in the month of May. Another DH, who not only had a great 2021 stretch run with the Red Sox but was available this winter, definitely makes the cut.

Schwarber leads the majors with 20 home runs this season, and that's in the middle of a current five-game homerless streak. His .947 OPS would be far and away the best among Red Sox qualified hitters. Maybe Boston couldn't have won the bidding war against the Philadelphia Phillies, but we'll never know, because Breslow reportedly never made an offer.

Chris Sale - ATL SP

Trading Sale was one of Breslow's first acts as CBO, and every year, we get a long list of reminders that it was the wrong move. After winning the Cy Young Award in 2024, Sale is still thriving two years later, with a 1.89 ERA and 0.87 WHIP, which have him in contention to take home the trophy again.

Sale will face the Red Sox at Fenway Park on Thursday, just to drive home the point that he's in a better place now.

Kyle Harrison - MIL LHP

The Red Sox are quickly learning that if the Milwaukee Brewers want one of their pitchers in a trade, they should be prepared to look like idiots. Harrison only threw 12 innings for the Red Sox before he was flipped to Milwaukee for Caleb Durbin, the worst qualified hitter in the sport. Meanwhile, he's putting up a 1.77 ERA and looks like a strong candidate to make the All-Star Game.

Chase Meidroth - CHW 2B

Maybe losing Meidroth in the Garrett Crochet trade isn't as big a deal as some of the other moves on this list, but the 24-year-old is proving to be exactly the kind of pesky hitter the Red Sox wish they had more of. He's like a right-handed Nick Sogard with more power, and once Kyle Teel returns from the injured list and Braden Montgomery is called up, the Chicago White Sox will be able to really flex those returns from the blockbuster in December 2024.

Mookie Betts - LAD SS

Betts is actually having a pretty terrible season so far, with a .596 OPS and negative-0.3 bWAR in 19 games. But his existence as a Los Angeles Dodger is just a constant reminder that the Red Sox traded their best player only a year after a World Series title because they seemingly didn't want to pay him what he was worth.

Curse of the Bambino 2.0? We're not trying to be melodramatic, but it certainly doesn't help that the Dodgers have won three World Series with Betts since the trade, and are the odds-on favorites to win a fourth this October.

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