Key Points
Bullet point summary by AI
- Ten MLB executives face intense pressure before the trade deadline, with some jobs potentially on the line.
- The Atlanta Braves and San Diego Padres have the resources to make major moves, but must decide whether to buy or sell.
- Choices on whether to trade star players or push for contention could define legacies and futures for several front offices.
Every MLB executive feels pressure this time of year, but not all pressure is created equally. Sure, Andrew Friedman feels some pressure to try and get the Los Angeles Dodgers a third straight World Series title, but it's not as if his job is at risk if they were to fall short. Sure, Chicago White Sox fans want to see a postseason appearance, but is Chris Getz really going to lose his job if they miss out?
These 10 executives, though, are facing a lot of heat — and could even have their jobs on the line ahead of the trade deadline.
10. Alex Anthopoulos, Atlanta Braves
Alex Anthopoulos already has a World Series win to his credit, and that helps ease some of the pressure he's dealing with, but the Atlanta Braves are in a position to win another title as things stand. They enter Tuesday's action with the best record in baseball despite a myriad of injuries and another disastrous Jurickson Profar contract, and they have more resources than they could've imagined entering the year.
Not only did Profar's extension give the Braves a ton of money to spend at the deadline, but prospects like Eric Hartman and John Gil have the Braves' farm system in much better shape as well. All of a sudden, Atlanta is in a perfect spot to go big-name hunting. Can Anthopoulos win the Braves a World Series at the deadline? We've seen him do it before.
9. A.J. Preller, San Diego Padres
No executive wants to make a splash this time of year more than A.J. Preller, who has acquired more stars at the deadline than I can count. But he needs to figure out whether buying is the right move for the San Diego Padres, who are three games over .500 but with a negative run differential and an offense that ranks dead last in the Majors in runs scored.
Preller should have money to spend with new ownership in place, and Ethan Salas is playing his way back to elite prospect status, but are the Padres really a splash or two away from competing with the likes of the Dodgers and Braves? Can Preller afford to sit back if he thinks the answer is no, given all he's done to try and win right now?
8. Buster Posey, San Francisco Giants
An argument can be made that the 29-43 San Francisco Giants are the most disappointing team in the sport thus far, and Buster Posey deserves a lot of that blame. Barring something unforeseen, San Francisco will be major sellers at this year's deadline, meaning that Posey must nail the returns in the deals he makes.
Both Robbie Ray and Luis Arraez are near locks to head elsewhere, and both should bring back a good amount of value. Ray is a proven innings-eater, and Arraez will probably be one of the best position players available. Posey will certainly try to dump at least one of Rafael Devers, Willy Adames or Matt Chapman as well. The Giants need to acquire impactful young talent. Failure to do so could lead to uncomfortable conversations.
7. Brian Cashman, New York Yankees
This might be the New York Yankees' best chance yet to win a title in the Aaron Judge era, as the American League is an absolute mess while teams like the Dodgers and Braves, while great, sure seem beatable. The Yankees' rotation is as good and as deep as anyone's when healthy, the same can be said about their lineup (with a healthy Judge) and even their bullpen has some quality pieces even if it lacks depth.
Cashman has seemingly unlimited job security, but at some point, results have to matter, right? He's done a good job to this point this season, even if the Yankees could use a catcher and more bullpen arms. But New York hasn't won a World Series since 2009. Failure to even get there in this American League would be a travesty.
6. Dana Brown, Houston Astros
Dana Brown took over a Houston Astros team that was the class of the AL and has watched them do nothing but regress under his watch. The Astros were fresh off a World Series title in the winter that Brown was hired, and since then, they've gone from an ALCS exit to a Wild Card Series exit to no playoffs at all. This season has been even worse somehow, as Houston is 33-41 on the year with one of the worst pitching staffs in the sport.
The Astros have looked like clear sellers for much of the year, but Hunter Brown is about to return, and they're as healthy as they've been all season. Might this be the excuse Brown needs to go all-in and try to guide Houston to the playoffs in a remarkably weak AL? Whether his team can make the playoffs or not could determine whether Brown has a job next season.
5. Dave Dombrowski, Philadelphia Phillies
It feels like now or never for the Philadelphia Phillies, considering the ages of most of the players in their core. They've done a great job getting back into postseason contention under Don Mattingly, but the holes on this team are abundantly clear. Not only do they lack rotation depth, but their lineup is both lefty-heavy and incredibly top-heavy.
Dombrowski has to do what he can to win now, but with a lot of money tied into this team and a very weak farm system, he faces clear limitations. It'll be interesting to see what he can pull off.
4. Jed Hoyer, Chicago Cubs
The Chicago Cubs' need for starting pitching might eclipse any need any other contender has right now. Matthew Boyd should be back from the IL very soon, but with Cade Horton out for the year and both Justin Steele and Jameson Taillon sidelined until the second half at least, the Cubs' rotation is in dire shape.
It'll cost a lot to address it meaningfully, though. Will Jed Hoyer be willing to meet said asking prices? I know that he recently signed an extension, so he probably isn't on the hot seat, but the Cubs missing the playoffs after signing Alex Bregman and trading for Edward Cabrera in the offseason would not be a good look. It's on Hoyer to ensure that doesn't happen, even if that means getting out of his comfort zone. And if Hoyer decides to sell, boy, he better get some exciting young talent.
3. Craig Breslow, Boston Red Sox
I don't know what the Boston Red Sox are going to do, as they're the fourth-worst team in the AL record-wise yet are only 5.5 games back of the third Wild Card spot. What I do know, though, is that whether Craig Breslow opts to buy or sell, he must get his moves right. I don't know if this fan base can take another bad deadline.
The Red Sox have said his job isn't in jeopardy, but a rough deadline could just be Breslow's final straw. Boston hasn't gotten any better since firing Alex Cora, and seemingly every move that Breslow has made since trading Rafael Devers away has aged poorly. A rough deadline would only make an already angry Red Sox fan base even angrier.
2. David Stearns, New York Mets
David Stearns felt more pressure than anyone entering this season, considering the New York Mets' stunning 2025 collapse — and so far, things have been disastrous. The Mets, despite a new-look roster, are eight games under .500 and in last place in the NL East. Injuries have hurt them, and they're still technically in the postseason race, but they've been as disappointing as anybody. And Stearns' offseason moves have a lot to do with that.
As is the case with Boston, I have no idea if the Mets will be buying or selling, but whether he chooses to trade Freddy Peralta and others for prospects or attempts to will this team to the postseason, Stearns must get this right. More moves that wind up going sideways will inevitably lead to conversations being had.
1. Scott Harris, Detroit Tigers
Nobody is even close to Scott Harris when it comes to executives under pressure right now, as he has to decide what to do with the best pitcher in baseball. Will the Detroit Tigers keep Tarik Skubal and try to make a postseason push? Or will they trade Skubal for what they can, punt on this season and hope for the best in 2027?
Arguments for both sides could be made, especially since the Tigers have been better lately, but again, regardless of what he picks, Harris better be right. If he keeps Skubal, the Tigers better go on a memorable run. Anything less than a World Series berth would make keeping him hard to justify, knowing he's almost certainly leaving in free agency. If he trades Skubal, he'd better nail the return. There is no excuse for trading Skubal for players who won't help the Tigers win in the not-too-distant future.
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