There's no denying the good that Craig Breslow has done as the general manager of the Boston Red Sox. The Garrett Crochet trade and subsequent extension have franchise-changing potential. Alex Bregman could be the new face of the Red Sox if he can extend him beyond the 2025 season. The pitching lab with Andrew Bailey has worked wonders with Andrew Bailey. And so on. Unfortunately, it doesn't erase the egregiously bad moves that Breslow has also made.
Put simply, there's a reason that the Red Sox finished only .500 in Breslow's first season as the general manager. There's a reason that Boston has struggled to get over the final hurdle in the 2025 season. Part of it is the remnants of Chaim Bloom, but some of it has also been the current Red Sox GM not making the right moves. Nobody bats 1.000 in the front office, but not everyone whiffs as badly as Breslow has to this point.
What are the worst Craig Breslow moves of his still-brief tenure? Somehow, we already have six (and it could've been seven if I was more critical of Lucas Sims) trades and signings that we have to talk about.
6. Trading Quinn Priester would look worse if not for a big return
At the 2024 trade deadline, arguably the most celebrated move that Breslow made was acquiring former Pirates top prospect Quinn Priester in exchange for Nick Yorke, who seemingly didn't have a path to the big-league roster in Boston. But the baffling conclusion to that came when the Red Sox then flipped Priester this offseason to the Milwaukee Brewers.
Let's be clear, Breslow got a nice return for Priester from the Brew Crew, getting the 33rd pick (Marcus Phillips) in the 2025 draft, Milwaukee's No. 7 prospect in Yophery Rodriguez and an organizational depth arm in John Holobetz. With Priester already fighting for a spot, that trade made complete sense. However, as Priester has inserted himself into the Brewers rotation, the move has continued to look worse for Breslow and the Sox.
Through 14 starts and 19 appearances with Milwaukee this season, the 24-year-old right-hander has a stellar 3.28 ERA with a 1.200 WHIP. It's not hyperbole to say that he's been part of the driving force that has propelled the Brewers to fighting for the NL Central crown with the Cubs. And as the Red Sox have eyed rotation upgrades throughout the 2025 season, it'd be nice to have someone pitching like that in the building.
The only reason that this move isn't higher-ranked as a worst move for Breslow is because of how good the return was. At the same time, it's still hard to swallow cutting bait on a pitcher who has immediately turned around to produce such great results on the mound.
5. Signing Walker Buehler, even for one year, at $21 million
Breslow made it a point to keep adding to the Red Sox pitching depth before the 2025 season, even while letting someone like Nick Pivetta loose. One such move was to take 2024 World Series hero Walker Buehler in free agency to a one-year, $21.05 million deal.
Make no mistake, there were a lot of fans who were excited about the move and thought that Boston was getting an absolute "dawg" to join the rotation and be a leader. However, what all of that failed to ignore, Breslow being the most notable culprit of turning a blind eye to it, was that Buehler simply hasn't been the same pitcher that he once was. That's been especially true in the regular season, both in 2025 with the Red Sox and even the year prior with the Dodgers.
While Buehler has started to shore up his performance around the All-Star break in 2025 season, his numbers still aren't pretty. Across 17 starts, the veteran righty has pitched to a 5.72 ERA with a 1.518 WHIP. Not to mention, his bad has been truly unwatchable, putting the Red Sox with a fat chance of getting a win by the end of the first inning on numerous occasions. And it's been tough to watch when that's the case.
The most bothersome part for Breslow is that he could've seen this coming. In 16 starts with LA a year prior, Buehler had a career-high (in at least 10 starts) 5.38 ERA with a 1.553 WHIP. Injuries have hampered him from being the player he once was on the mound, and it's difficult to now justify giving a player like that north of $20 million. It was a gamble on a bounce back that simply didn't pay off.
4. Trading for Danny Jansen as their much-needed right-handed bat
Red Sox fans were immensely frustrated with Breslow at the 2024 trade deadline because of what many deemed as fence-sitting. There's perhaps no better indication of that than the offense direly needing to add a right-handed bat and the front office's solution to that being a trade with the Blue Jays for catcher Danny Jansen.
First and foremost, the Red Sox really didn't need catching depth. So to land a right-handed bat that didn't have an immediate or natural position to play upon his arrival in Boston was a wild move in itself. But more damning was the fact that Jansen wasn't an impact bat in the slightest, which anyone could've told you with one look at his .671 OPS in Toronto before being dealt.
To make it look even worse, though, Jansen was worse with the Red Sox once he arrived. Across 30 games, he slashed just .188/.323/.300 with three homers standing as his only extra-base hits. It's telling that he's best remembered for now being a meme among fans because of how many times the broadcast mentioned him being the first player to play for different teams in the same game due to a previously suspended Sox-Jays matchup that resumed after the trade.
Because of this trade, there might be fears from fans for years now that, when the Red Sox need an impact bat, they'll just end up with the latest iteration of Danny Jansen.
3. Trading for Luis Garcia at the 2024 deadline
Boston was clearly trying to shop the bargain bin for relief pitching down the stretch at the 2024 trade deadline and, to Breslow's credit, you would've thought that he found a ripe option to pick in landing Luis Garcia. So much so, that Breslow gave up four prospects to the Angels to acquire the veteran right-hander's service. Had those prospects already made noise, this would be an even worse move. But it's still pretty bad with how things have played out to this point.
After Garcia had posted a more than serviceable 3.71 ERA and 1.168 WHIP with the Angels before the trade, he became legitimately unwatchable when wearing a Red Sox uniform. He appeared in 15 games with Boston and did so to the tune of an 8.22 ERA and a 1.630 WHIP. In just 15.1 innings of work, he gave up 2.3 home runs per nine innings and was a disaster that cost the team games in relief.
Obviously, it would be somewhat hard to see a blow-up of that magnitude coming for Breslow or anyone. At the same time, we're operating with 20-20 hindsight and the trade was an absolute failure. Garcia was traded for in an effort to improve and shore up the bullpen, but he instead made that group actively worse and helped erase any semblance of a chance that the Sox had of making the postseason, no matter how slim.
2. Trading Rafael Devers to the Giants after public feud
Most people were probably thinking that the Rafael Devers trade would be No. 1 on this list. The pure shock value of moving a star slugger 1.5 years into a 10-year contract warrants that type of reaction in most cases, without question. However, there's so much nuance with the Devers trade and Breslow's role in it that, while it's still bad — especially given the return — it doesn't yet qualify as the worst move that the GM has made in Boston.
If you're just looking at the trade in a vacuum, it's honestly justifiable why Breslow made the move. Devers has consistently made it clear since he was dealt to the San Francisco Giants that he was being spiteful and petty as a malcontent in the Red Sox clubhouse. The organization and player had clearly reached a point of no return that was negatively affecting the team, so it made sense to move on. For the action in that moment and to get a high-upside young arm (Kyle Harrison), a workable reliever (Jordan Hicks) and a higher-end prospect (James Tibbs III), the return should've been bigger, but it was passable.
Having said all of that, Breslow also gets credit, or perhaps more accurately blame, for why he and the Red Sox ended up in that position with Devers. His lack of communication regarding the team's pursuit of Alex Bregman in the winter leading into the 2025 season ultimately led to Devers' unhappiness. He didn't want to move to DH, or he at least wanted a heads up that was a possibility. Moreover, as Devers was later asked to fill in for Triston Casas at first base after an injury, he refused, which led back to the switch to DH but also Breslow's lack of contingency plan at first base.
The early returns on Devers in San Francisco were mixed, but that doesn't make the notion of the Red Sox trading their best offensive player for less than face value easier to swallow. The deal itself might not be the worst given the situation, but Breslow gets blamed because he's the one who led Boston and Devers into that situation.
1. Trading Chris Sale to the Braves for next to nothing
For as frustrating as the Devers situation is, there isn't a worse move than Breslow trading Chris Sale to the Atlanta Braves for Vaughn Grissom. In the context of the time of the deal, Sale's unbelievably bad luck with the Red Sox seemed to indicate that he might just need a change of scenery and a fresh start somewhere else. I get that. But at the same time, what Sale went on to do and what Grissom has done since the trade make it an outright catastrophe for Boston.
Starting with the one-player return that the Sox got, Grissom played 31 games for Boston in the 2024 season, managing only a .465 OPS after dealing with a spring training illness and spending most of the year recovering or in Triple-A. The highest level of the minors, meanwhile, has been where he's spent the first 100+ games of the 2025 season as well, and Boston has shown no urgency to try and get him back up to the big leagues anytime soon.
All Chris Sale did, contrarily, was go to the Braves and win the National League Cy Young. While injuries have popped up again in the 2025 season, he's been nothing short of dominant since the trade. He threw to a 2.38 ERA with a 1.013 WHIP and striking out an NL-high 225 batters across 29 starts in his first year in Atlanta, and had a 2.52 ERA with a 1.164 WHIP with 114 strikeouts in 15 starts before the injuries in mid-2025.
So to recap, the Red Sox traded a guy who won the Cy Young for a prospect they don't think is good enough to play in the major leagues right now. If that doesn't qualify as the worst trade that Breslow has made since he became the GM in October 2023, then I don't know what to tell you.