Being a baseball general manager is never easy. They are equal parts budget balancers and talent evaluators, as well as shrewd negotiators and, in some cases, the bringers of bad news to those no longer associated with the club. It’s a thankless job in the best of times and can be a real pressure cooker at other times, particularly during the MLB trade deadline.
Trade season forces baseball executives to take a long, hard look at their clubs—and farm systems—to make some tough decisions and then face the music from the media afterwards. Some are buyers, some are sellers and others are somewhere in between.
They all have one thing in common: pressure. They’re all feeling it at this time of year. Here are the seven GMs feeling it the most in the lead-up to the Aug. 3 deadline.
Brian Cashman, New York Yankees
Cashman is between a rock and a hard place in the lead-up to the deadline. The Yankees boast a solid bullpen and elite starting pitching, but the Aaron Judge-less offense has scored fewer runs than all but four teams since the big man went down with an injury. Yet, New York still resides in the AL, which is pacing for one of its weakest seasons historically. The conundrum, essentially, is that the road to pennant No. 42 looks easier than ever, but the car won’t start without Judge.
Does Cashman, who needs a catcher and a swing-and-miss reliever at minimum, go big at the deadline in the hopes that Judge returns for the playoff push? Or does he improve at the margins while holding onto some of his most prized prospects?
Dave Dombrowski, Philadelphia Phillies
Just a few months ago, the Phillies’ sluggish start would have put president of baseball operations Dave Dombrowski in position to sell. The club has since surged to the second-best record in the National League since firing ex-manager Rob Thomson, thus thrusting Dombrowski into the buyer’s line.
Complicating things is the fact that Philadelphia’s farm system has been depleted due to recent promotions, trades and injuries, giving the Phillies executive little to work with as he scours for outfield, bullpen and starting pitching help.
Scott Harris, Detroit Tigers
If the Tigers had a defining song for the next week or so in the lead-up to the Aug. 3 trade deadline, it would be “Should I Stay or Should I Go” by The Clash. That is the defining question for Tigers president of baseball operations Scott Harris, who must determine whether to keep back-to-back AL Cy Young Award winner and pending free agent Tarik Skubal in a push for October in a weak AL, or deal the ace for a sizable return while he still can.
Detroit has surged since Skubal returned from surgery to remove loose bodies from his pitching elbow, but is this roster built to succeed in the postseason? Expect Harris to mull the should-he-stay-or-should-he-go dilemma up until the 6 p.m. ET deadline on Aug. 3.
David Stearns, New York Mets
Stearns’s job isn’t in imminent danger (yet) but after a series of questionable decisions helped lead to a collapse down the stretch of 2025 and the disappointment of 2026, he’s certainly under the microscope more than he’d like. Nearly 20 games under .500, Stearns knows he needs to sell. The tricky part is figuring out who.
There are bad contracts (Bo Bichette) and underachievers (Freddy Peralta) among Stearns’s tradeable pieces, making this an unenviable task. Yet, the Mets executive can begin to right some of his wrongs by taking advantage of a seller’s market and dealing some of his valuable relievers for prospects.
A.J. Preller, San Diego Padres
The rent is now due on Preller’s aggressive strategies of deadlines past, as he sits with an aging roster and farm system that is a shell of itself, particularly after last season’s summer spending spree that netted the nearly unhittable Mason Miller.
Miller’s dominance has, however, opened the door for Preller to potentially recoup some of the high-end, young talent he’s dealt away. Yet, San Diego sits just close enough to a playoff spot to give the Padres executive pause on dealing the flamethrowing reliever. The question is, will Preller be able to ignore the little voice in his head telling him to buy?
Dana Brown, Houston Astros
The signs of Astros owner Jim Crane’s impatience were already there, when both general manager Dana Brown and manager Joe Espada were not offered contract extensions this past winter. Then, the Astros went out and played middling baseball for four-plus months this season. Given Houston still has a chance in the worst division in the worst league, selling would seem to be out of the question, despite a stale farm system in need of restocking.
The latter point will make Brown’s potential task as a buyer quite difficult. He’ll need to navigate the high-priced seller’s market in search of upgrades with nary a single elite prospect to dangle all while Crane breathes down his neck.
Buster Posey, San Francisco Giants
The Giants entered 2026 smelling like a rose, budding with the optimism that came with the hiring of new manager Tony Vitello and the dreams of a return to the postseason. Nearly 20 games under .500 with nearly a week to go until the trade deadline, the stench around the club now portends a potential summer sale.
But it won’t be easy. The Giants are bogged down by some of the worst contracts in baseball, and some of their best trade chips are rentals, not the club-controlled assets especially coveted by rival teams. Yet, Posey can take a step in the right direction by at least netting some prospects for veterans in what would otherwise amount to a lost season.
