The 6 MLB front office executives under the most pressure this trade deadline

As the July 31 MLB trade deadline rapidly approaches, the intensity is rising across all front offices in the league. Whether a team is buying, selling, or stuck somewhere in the middle, every executive is feeling the heat. The pressure to make the right moves is palpable, and the decisions made in the coming days could shape the rest of this season — and potentially the future — for many franchises.

Teams with postseason aspirations are scrambling to bolster their rosters, looking for impactful additions to strengthen their odds in the playoff push. At the same time, they’re also seeking to deepen their organizations to guard against the inevitable injuries that occur down the stretch. Ever since MLB eliminated August waiver trades six years ago, the July deadline has taken on added significance, leaving teams with just one shot at meaningful midseason acquisitions.

What complicates matters even more this year is the relative scarcity of definitive sellers. With only eight clubs — the Orioles, Athletics, White Sox, Marlins, Braves, Nationals, Pirates, and Rockies — trailing the wild-card race by more than six games, the market is tight. That puts even more strain on general managers and heads of baseball operations to deliver results under immense scrutiny. While every front office is being watched, a handful of them are under especially intense pressure to execute transformative trades that could define their tenure.

Let’s examine the executives whose decisions this trade season will be under the brightest spotlight:

1. Mike Elias – General Manager, Baltimore Orioles

Among all MLB executives, Mike Elias arguably finds himself in the hottest seat. Industry insiders suggest that his position might even be in jeopardy, should he fail to guide the Orioles through a productive trade deadline.

Elias has built a reputation as one of the top talents in player development and amateur scouting, dating back to his time with the Astros. Since taking over in Baltimore in late 2018, his drafts have been widely praised — including the 2025 MLB Draft, where many analysts declared the Orioles as having one of the best hauls.

But despite these successes on paper, Elias has yet to fully translate that into a dominant Major League roster. While the Orioles did win 100 games in 2023 and made playoff appearances in recent seasons, this year has been plagued with setbacks. Injuries, underperformance, and general bad luck have Baltimore shifting from contenders to likely sellers.

Still, the Orioles find themselves in a position of leverage. If teams like the Diamondbacks don’t enter the seller’s market, Baltimore may control the narrative at the deadline, boasting some of the top available talent. In a recent interview on MLB Network Radio, Elias hinted at prioritizing deals for players with expiring contracts, though he didn’t close the door on other potential trades. The Orioles’ best trade chips include veteran players such as designated hitter Ryan O’Hearn, center fielder Cedric Mullins, starting pitcher Charlie Morton, and relievers Gregory Soto and Seranthony Domínguez — all of whom are nearing free agency. The club could also consider parting with long-term assets like closer Félix Bautista or outfielder Ramón Laureano, depending on the offers.

A smart, calculated deadline could help Elias reshape Baltimore for a powerful resurgence in 2026. But if he fumbles, the organization may begin looking for new leadership — possibly demoting Elias or replacing him altogether.

2. Ben Cherington – General Manager, Pittsburgh Pirates

Cherington’s tenure in Pittsburgh is approaching its sixth year, and the results have been mixed. While he’s assembled a respectable pitching staff, the offense remains weak and inconsistent. The time has come for Cherington to address this shortcoming decisively.

He does have valuable assets to offer. Starters Mitch Keller and Andrew Heaney, along with relievers David Bednar and Dennis Santana, could be moved for promising young bats. Keller, under contract through 2028, would be the most high-profile departure. Trading him could open a spot for top prospect Bubba Chandler, who’s currently thriving at Triple-A. Additionally, the Pirates expect starter Jared Jones to return next season from elbow surgery, giving them a reason to consider retooling now.

If Cherington can turn a few veteran arms into a group of near-MLB-ready position players, he could solidify his standing with ownership. Failing to act, however, might lead to his departure before the 2025 season begins.

3. Jed Hoyer – President of Baseball Operations, Chicago Cubs

Hoyer, along with general manager Carter Hawkins, has done a commendable job guiding the Cubs back toward relevance. After two consecutive 83-79 seasons, Chicago now finds itself in a heated battle for the NL Central crown with the surging Milwaukee Brewers.

Despite their success, ownership has not yet offered Hoyer and Hawkins contract extensions — both are signed through 2025 — meaning the pressure is on to prove that the Cubs are legitimate contenders. At the deadline, they’re eyeing reinforcements across the board: a starting pitcher, an upgrade at third base, bullpen depth, and bench help. Fortunately, the Cubs possess one of the stronger farm systems in the league. Top prospects like Owen Caissie and Kevin Alcántara could serve as valuable trade pieces.

Given the current competitive window, the Cubs can’t afford to stand still. This deadline could be pivotal in propelling them from good to great.

4. Perry Minasian – General Manager, Los Angeles Angels

Since stepping into the Angels’ GM role in late 2020, Minasian has tried to lead the club out of mediocrity. However, despite building a promising young core featuring Zach Neto, Logan O’Hoppe, Nolan Schanuel, and Jo Adell, the Angels have consistently underperformed, particularly in pitching.

Currently ranked 26th in team ERA and 29th in WHIP, the Angels’ staff is one of the worst in baseball. And while Minasian received a contract extension through 2026, his job security is far from guaranteed. The lack of impact from the farm system has forced him into frequent short-term fixes, a pattern that isn’t sustainable.

This trade deadline represents a critical opportunity. Whether the Angels opt to be buyers or, more realistically, sellers, Minasian must prioritize pitching — at every level of the organization. The path he chooses may be dictated by owner Arte Moreno, but ultimately, Minasian will be judged by how much he improves the team’s trajectory.

5. Jerry Dipoto – President of Baseball Operations, Seattle Mariners

Seattle’s championship window is wide open, but it won’t remain that way forever. With a top-tier rotation and an MVP-level campaign from catcher Cal Raleigh, now is the time for the Mariners to go all-in.

Fans have grown impatient with the team’s conservative trade strategies, and Dipoto’s front office cannot afford another deadline with minimal movement. Fortunately, ownership is prepared to increase payroll if necessary, and Seattle boasts one of the best farm systems in the league — rich in assets that could be flipped for immediate help.

Seattle is reportedly searching for one more big bat and a reliable bullpen arm. Potential trade targets include Ryan O’Hearn (Orioles), Josh Naylor and Eugenio Suárez (Diamondbacks), Luis Robert Jr. (White Sox), and Kyle Stowers (Marlins). A deal or two could turn the Mariners into legitimate World Series contenders — something the franchise has never achieved.

6. Mike DeBartolo – Interim General Manager, Washington Nationals

Appointed only recently after the firing of longtime executive Mike Rizzo, DeBartolo has a rare chance to prove himself. While the Nationals are expected to bring in a new president to oversee operations in the offseason, a successful trade deadline could give DeBartolo a shot at retaining his role as GM.

His approach appears to be focused on making minor moves around the edges — particularly in the bullpen and bench — rather than trading away core players. However, if he takes a bold swing, dealing one of the team’s valuable but non-essential contributors for a sizable prospect return, he could cement himself as a long-term fixture in Washington’s front office.

If his deadline is unremarkable, though, he risks being passed over when permanent hires are made.