Key Points
Bullet point summary by AI
- The Boston Red Sox enter the 2025 season with a rocky 2-8 record, sparking fan unrest and calls for leadership changes.
- Recent offseason moves, including a high-profile trade and free agency decisions, are under intense scrutiny for their impact on the roster.
- Critical evaluations of these transactions reveal significant missed opportunities that could affect the team's playoff contention this year.
At 2-8, the sky is falling in Boston. Red Sox fans are chanting “Sell the Team!” with John Henry in the ballpark. But things can only get better from here — really, for a team as talented as the Red Sox, it can’t get much worse.
There are holes on the roster, however, and it’s something I’ve been concerned about since the winter. In trading Rafael Devers and shedding the entirety of his contract, the team should have easily had the money to retain Alex Bregman, a player they loved both in the clubhouse and on the field. Instead, they watched him depart for the Chicago Cubs. They had interest in Bo Bichette, Kyle Schwarber and others, and instead ended the winter with Willson Contreras, Caleb Durbin and Isiah Kiner-Falefa.
But let’s step back and look at the Devers trade. After I broke the news, the comments ranged from “WTF!” to “were you hacked?” to eventually “what’s the return?”
The return, of course, was Kyle Harrison, Jordan Hicks James Tibbs III and Jose Bello. It was regarded as light by many, with some referring to the move as a pure salary dump. The Red Sox then flipped Harrison to the Brewers for Durbin. They traded Hicks to the White Sox. They traded Tibbs III only weeks later to the Los Angeles Dodgers for a couple disastrous months of Dustin May. (Bello, meanwhile, remains in Boston.)
So 75% of the Devers return is elsewhere … and now they’re tearing it up elsewhere.
Trading Kyle Harrison looks like a mistake

To be fair, I love Durbin. I think he’s an excellent player and his short stature should remind many folks in Boston of Dustin Pedroia. He will be an impact player. Yes, I realize he’s off to an incredibly slow start. But he will be better.
My initial reaction to the trade, and something I shared numerous times on The Baseball Insiders, was that the Brewers clearly saw something in Harrison they could fix. Not long ago, he was regarded as the Giants’ latest version of Madison Bumgarner. Expectations were high for Harrison in San Francisco. It did not work out, he was traded to Boston and the Brewers viewed him as a buy-low candidate on a player they could not previously get their hands on.
Since spring training, Harrison has impressed team officials. They changed subtle things with him, including a new changeup and also his preparation between starts, and it’s worked wonders. He looks exactly what the Giants hoped he’d become and has carved out a role in Milwaukee's rotation.
It should be little surprise considering how good the Brewers’ pitching development is. Last year, they did it with another highly regarded prospect in Quinn Priester — also acquired from the Red Sox — and now it appears they did it again with Harrison.
James Tibbs III is breaking out in Los Angeles

Right after the Red Sox acquired Tibbs III, I had two prominent league sources reach out and say that Tibbs III was likely to be moved again at the deadline.
For who?
Well, it was for Dustin May, and the reaction initially from league sources was surprise. May, a former top prospect, was being openly shopped at the deadline and had posted a 4.85 ERA in 19 games in 2025. Getting Tibbs III, a high-end prospect and former first-round pick, was a lot of value for a player of May’s status on an expiring contract.
Tibbs III has been a revelation in the Minors this season, hitting .474/.535/1.184 with a 1.719 OPS, seven home runs and 13 RBI in Triple-A. It would hardly be a surprise if he debuted at the MLB level this season and contributed within the Dodgers’ outfield, perhaps even during the postseason.
The Tibbs III for May swap made little sense in the moment. But it looks like a huge swing and miss for the Red Sox, especially with May departing for the St. Louis Cardinals in free agency.
Should we overreact?
I’m usually a big believer that we shouldn’t panic too soon, especially not two weeks into the season. But the Red Sox needed to turn the saved money from the Devers trade into adding one of Bregman, Schwarber or Bichette. They did not.
I’m still convinced that the Durbin for Harrison trade will be a deal that helps both sides. Do not give up on Durbin by any means; he’ll be a good player for a long time. But the Tibbs III for May trade already looks like a mistake.
Sometimes the best trades are the ones you don’t make at all. And in Breslow’s case, perhaps he made one too many, and didn’t prioritize the right players in free agency.
