Red Sox CBO Craig Breslow has previously stated that he wants to "bolster" at the deadline. However, many of the Red Sox fans aren't buying what he's selling (get it?). They believe he should do said selling because they believe he waved the white flag when he traded Rafael Devers.
Now, while there's some truth to what both Breslow and the fanbase are claiming about the Devers situation, it's interesting to see if Breslow will either buy or sell depending on the results. There's already a piece about him going through with his word and buying at the deadline, no matter the result, because he "believes" in this team. But there isn't one about if he DOESN'T follow through with his words.
Think about it: The Red Sox have been notorious for saving money since the turn of the decade, and ownership is completely hands-off on operations. Breslow is treating the Red Sox like it's a small market (or medium-sized market, rather) when it's supposed to be a big market. The team is currently responsible for $249 million of their 2025 payroll and is projected to be around $197 million for 2026. Given all the bloated contracts that the Red Sox have from the Bloom era, Breslow doesn't want to deal with that, and just like Devers, he'll shed as much as possible.
So, who are the possible names that could be dealt in this year's deadline? These players are as follows:
1. Walker Buehler
2. Lucas Giolito
3. Aroldis Chapman
4. Abraham Toro
5. Greg Weissert
6. Trevor Story
7. Jarren Duran
Now, those are a lot of names, and most of them are already written off by sports writers across the nation (Chapman, Buehler, Duran, & Story mentioned). But who's willing to take them?
Walker is as good as gone by the end of July, and that's either by DFA or (a big IF on this one) by trade, and someone's willing to take on that salary. But most likely, it would have to be a package among other prospects/players. He's absolutely infuriating in Boston right now, and he's a shell of his former self. He signed a 1-year, $21M deal with Boston in the offseason, hoping to come back to that Cy Young contender that he once was. That experiment has not panned out in the slightest, and it's time to let go. He'll be good for a salary dump with a team like, say, Colorado.
"I don't want to be traded. I really love it here.", Lucas Giolito - 2025
Poor naive Giolito, he doesn't know how much Breslow doesn't care. Unfortunately, baseball is business...and if there's a good return for him, Breslow will take it. But who would want him? He's on the books for $19.25M this year with a $12.5M club option for the next. It's expendable, and the ones that could take this contract would be five teams: the Diamondbacks, Cardinals, Reds, and the Cubs.
The Cardinals and the Cubs are in need of pitching help, especially for a #3 or #4 starter, and Gio fits this role. The Cubs, for one, need it the most with Shota Imanaga just returning and Justin Steele needing Tommy John Surgery, effectively ending his season. The Cardinals' best pitcher is 35-year-old Sonny Gray, who IS holding his own, but it's not sustainable for team success when the rest of the rotation has a 4.28 ERA.
Aroldis Chapman is the most obvious one of the bunch, as he's 37 years old on an expiring contract, who's arguably one of the better relievers in baseball this season. He'll generate a good return for any team he goes to, which are most likely the D-Backs, Angels, Dodgers, or the Phillies.
Any of these four teams are big candidates for a phone call to Breslow. The Diamondbacks had youngster Justin Martinez as their closer, and now he's out for Tommy John Surgery, ending his season. The Angels had originally signed (funny enough) Kenley Jansen, but he had an ERA over 4 with a risk of not being a sustainable arm. Chapman would be a better substitute and move Kenley as a setup arm.
The Dodgers, funny enough, want more talent. They're always a candidate for acquisitions, especially for pitching. They've always been known to acquire better pitchers at the deadline. But the Phillies? They arguably need Chapman the most. Their current closer, Jordan Romano, is having the worst season of his career. An ERA over 7, with an ERA+ of 59, which is almost unheard of for a closer.
Their only good pitcher was Jose Alvarado, and he's been suspended 80 games for the use of PEDs. An arm like Chapman, with the season he's having? He'll be a must-want player for them right now and could get an outstanding return if Breslow plays hardball to their desperation for a good reliever.
Abraham Toro, a 28-year-old journeyman, has been one of the more surprising assets to the Red Sox lineup. He's batting .286, with 5 HRs and 9 doubles in just 42 games with the club. He was, once upon a time, a top-30 prospect in the Astros' formerly VERY fertile farm system. He was traded to Seattle in a package for reliever Kendall Graveman in 2021.
Since then, he's been part of the Seattle, Milwaukee, and formerly Oakland ballclubs. He was then signed to a minor league deal with the Red Sox in 2025 and was called up to play first base as a substitute for Triston Casas, after he tore his right patellar tendon, ending his season prematurely. What was seen as a temporary sub turned out to be rather of an antidote.
He'll be a great depth piece with the highest value that he's ever had in his still-young career. Ironically, the Astros are one of the three teams that could need a piece like him to bolster their depth. They're already in good shape with their roster construction, so why not just get a small piece to iron the lineup out? Many teams do this when contending.
The other teams that would want his services are the Cubs. Now with the Cubs, he'll most likely be in the utility role from third to first, alternating with rookie Matt Shaw and Michael Busch. The return they'll get wouldn't be the best because it would seem more like the Red Sox wanting to get rid of him due to the Cubs already having players in those positions (and are doing passably).
As for the return? It could most likely be a player swap, but why not ask for a top-30 prospect? Can't hurt to try, right? Both the 'Stros and the Cubbies can bulk one up in a trade, like say, RHP Will Sanders (Cubs #20 prospect) or RHP Jose Fleury (Astros #14 prospect who's due a call-up to AAA). It could work out pretty well, given the latter's previous trading with the Red Sox which turned out to be Wilyer Abreu in that infamous Christian Vazquez trade.
Greg Weissert, a man who leads the league in games played for pitchers, but has a sub-3.00 ERA and 4 blown saves on the season. "That's our fault, we misused him", Brad Pitt as Billy Beane would say in Moneyball (2012).
The teams that could still use him on the roster are the Diamondbacks, Rays, Angels, and Reds. The D-Backs, over these past couple of seasons, have had one of the worst bullpen arms in baseball. How did they miraculously make the 2023 World Series? No one has a clue about that team ERA at 4.70 this season. At this point, they need anything that can stick.
Weissert is a candidate, foolish or not, and the D-Backs are the gullible recipients of his services. They could fork up a decent return if Breslow negotiates properly. He could put him in a package with Chapman for this deal. One prospect that they could get from their farm with that trade could definitely be someone like RHP Daniel Eagen, a very promising prospect out of college who's excelling with a 2.97 ERA in High-A ball with 83 strikeouts.
The Rays could give up a good prospect or a player swap for him, like RHP Edwin Uceta, who's having a down year with a 5+ ERA, but can thrive in Bailey's system. They could also give up a prospect in the late 20s, like RHP Jose Urbina (#28), who's doing amazing in Single-A right now with an ERA of 2.10 with 12 saves and 66 strikeouts in only 12 games. I'd suggest the latter for Breslow here.
The Angels and the Reds are all deaf for pitching help right now, especially in that bullpen. However, knowing how the Angels have poorly approached the deadlines these past few seasons, they could just stand pat like they did last year or do a minimal deal. Weissert is perfect for that, and they could get a prospect for him, albeit not that strong of one, since the Angels' farm system has been barren since 2014. But the Reds can definitely fork up a bit for Weissert. RHP Ty Floyd (#18) could be a piece they acquire as well.
Finally, in a healthy season for the Red Sox, Trevor Story is a serious candidate to be traded. It's really a shame that many believe that just because his contract is worth $23M a season, it means that no GM wants a player with that much mileage on him. Sure, he wouldn't get a great return, but the pedigree is still there from what Story has shown this season.
Story's a very hot-and-cold player, especially this year. He's batting .244, but with 12 HRs on the season, and is playing excellent defense at shortstop. While it could be hard to find a team that wants a player with this much mileage and questions about his sustainability, this year could be the only chance that the Red Sox have at getting rid of his contract.
The Rays and the Brewers are teams that could want him, but the Rays are a big question mark given his bloated contract. The Brewers, however, could be more than willing to add a power piece to their lineup (that is desperate for power, by the way, as they're 22nd in team HRs). Here's the advantage as well: Not many shortstops will be on the market this year, but if the Red Sox put Story on the block, the Brewers could most likely be on the other telephone line.
To sum this all up, Trevor Story has enough shortstop defense and power upside, in a weak shortstop market, to have trade value. But, and it's a big "BUT", the Red Sox would almost certainly have to absorb some money to get anything more than a token return. So with that in mind, IF the Red Sox want to pony up about $10M to $15M over these next few seasons left in the deal (until 2028), they can get a prospect or two plus a depth piece.
They could get a good return for him, which could be RHP Bishop Letson (#12) and RHP Bryce Meccage (#13), and/or Garrett Mitchell as a backup outfielder (depending on whether they eat some salary or not).
Again, baseball is business...and it'll be sad to see Jarren Duran go, but there's a logjam in the outfield. Many execs believe that Wilyer Abreu is going to stay, while Duran will be heading somewhere else at the deadline. While it'll be sad to see him go, the return could be amazing for a player who's one, under control until 2029, is almost never injured, and is a doubles and triples machine that's aggressive and fast around the bases.
Many teams want him, but the more probable candidates are the Phillies, Dodgers (no shocker there), Padres, and the Blue Jays. Let's start with the Phillies.
The Phillies have Max Kepler in left field...if that's not a recipe for a disaster, then the world isn't spinning. Kepler is a decent player, but more of a bench bat nowadays. They need an outfielder like Jarren, and they'll be desperate enough to fill his services. Max Kepler could be involved in the trade, but the return would definitely be bigger than just a player swap; more like RHP Andrew Painter (#1) and RHP Moises Chace (#8) as well.
The Dodgers have always had a fertile farm, but not a lot of top pitchers in their farm system besides LHP Jackson Ferris (#4). The Padres do have pitchers, but most of them are in AA or lower (the ones that are doing well), like LHP Kash Mayfield (#3) or LHP Boston Bateman (#5), so both of them will have to fork up some major league players as well, like reliever Jeremiah Estrada (Padres) or Alex Vesia (Dodgers).
The Blue Jays are an intriguing team to watch. They've missed out on a lot of players like Shohei Ohtani and Juan Soto. But if they can swoop in with a good offer, like RHP Trey Yasavage (#2) and LHP Kenry Rojas (#8), along with someone like Davis Schneider or Brendan Little (who's been amazing in the bullpen this year for Toronto), it would be a passable deal. But if Breslow is wise, he can play into the fact that they haven't acquired big-time talent because they've been coming up short, it may get them desperate enough to give up another prospect. A prospect like RHP Juaron Watts-Brown, who's a big up-and-comer in their system, then it could play into the Red Sox's hands.
Truth be told: The Red Sox don't have to trade anybody, but if they're wise about it, it's best to sell. Nothing is going for them this year, and loading up on pitchers in the prospect pool will only help them in the future. It may stink for the fans, but it has to be done. Barring a total collapse from the Rays and the Blue Jays this season, the Red Sox will not be making the playoffs in 2025. Retool and bolster next year, which is probably what Breslow meant in the first place.