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

New York Times

3 days ago

MLB front offices have only nine days left until the trade deadline and the pressure is mounting on every team, from the buyers to the sellers to the clubs that are in between.
Contending teams are trying to find ways to improve their rosters for the pennant race and the postseason through trades. They're also trying to add organizational depth to protect against unexpected injuries the rest of the way, since MLB changed the rules six years ago to eradicate trades via waivers in August.
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It's another tricky trade marketplace for executives to navigate due to the dearth of sellers and a playoff picture with only eight teams — the Orioles, Athletics, White Sox, Marlins, Braves, Nationals, Pirates and Rockies — more than six games out of a wild-card race.
Life as a general manager or president of baseball operations at the trade deadline is an intense time, and every front office — regardless of market, track record or place in the standings — is under the microscope to some degree. But certain front offices, from clear sellers to aggressive buyers, face more pressure to deliver difference-making deals than ever before.
Here are the front offices and executives under the most pressure to make significant moves this trade season.
No executive is under more pressure at this trade deadline than Elias, with many in the business believing his job could be in jeopardy.
He has been one of the best in the industry in terms of amateur draft selections, from his days rebuilding the Astros to his tenure with the Orioles (November 2018 to present), including this year's draft, with many analysts believing the Orioles 'won' the 2025 MLB Draft. However, in Baltimore, he hasn't yet turned his strong drafting track record into a World Series-caliber major-league team, though the Orioles did win 100 games in 2023 and make the postseason the past two years.
This season, anything that could go wrong has gone wrong, and now Baltimore must sell at the deadline and prepare for next year. The good news for the Orioles is they're in a strong position to take advantage of their misfortune and a thin trade market. If the Diamondbacks don't become sellers at the trade deadline, the Orioles will be the headliner among selling teams, with the most talented players to offer. Elias appeared on my MLB Network Radio show on Sunday, and he made it clear that players on expiring contracts will be at the top of their list to move, but he didn't rule out trading other players and is in the process of doing his due diligence.
With the trade deadline looming, it seems like phones are ringing in the Warehouse ☎️ @Orioles | #Birdland 🔗 https://t.co/iXax8hx4iO pic.twitter.com/dxU1Dyz14E
— MLB Network Radio on SiriusXM (@MLBNetworkRadio) July 20, 2025
If the Orioles can make strong deadline deals, it could go a long way toward establishing them as legitimate contenders in 2025, once their pitchers get healthy and their young position players start to play at higher level, which many of them can do.
So, let's look at what the Orioles have to offer in deals: It starts with position players like DH Ryan O'Hearn and center fielder Cedric Mullins and includes veteran starting pitcher Charlie Morton and relievers such as Gregory Soto and Seranthony Domínguez. All of them are impending free agents. The Orioles could also consider deals for players like closer Félix Bautista (under team control through 2027) and outfielder Ramón Laureano (2026 club option) as well.
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A strong deadline could save Elias' job. A lackluster one could result in the Orioles bringing in someone new to the front office to work under Elias or maybe even showing him the door. I believe he'll get the job done.
Cherington has had nearly six years to rebuild the Pirates, and although he's assembled a competitive pitching staff, he hasn't built an everyday lineup that's good enough to compete. He is under a lot of pressure to make deals at this trade deadline to improve their offense in all phases.
The good news for Cherington is he has plenty of pitchers he can dangle, including starters Mitch Keller and Andrew Heaney and relievers David Bednar and Dennis Santana. If the Pirates trade Keller (signed through 2028), they could promote top pitching prospect Bubba Chandler, who is at Triple A, and they will be getting back another bright young starter, Jared Jones, sometime next year, after he has recovered from the elbow surgery he underwent in May.
If Cherington can make trades in the coming days that turn the above-mentioned four veteran pitchers into eight hitting prospects who are close to the big leagues, it could go a long way toward keeping him in Pittsburgh a few more years. If not, he could be unemployed come October.
Hoyer and his GM, Carter Hawkins, are signed through the 2025 season, and both deserve contract extensions for the great job they've done in hiring manager Craig Counsell and rebuilding the Cubs' roster into a legitimate World Series contender. They've also excelled in building a strong farm system. However, if ownership hasn't extended their contracts by now, there's pressure on both to keep adding at the deadline to get this team over the top.
Chicago is in a fierce race in the NL Central with the Brewers, who have won 11 in a row to overtake the Cubs atop the division. Milwaukee looks formidable, especially with the addition of hard-throwing rookie Jacob Misorowski and veteran Brandon Woodruff off the injured list.
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The Cubs need to be active at the deadline. They're focused on acquiring a starting pitcher and an upgrade at third base as well as bullpen and bench reinforcements. They have a stocked system to trade from, led by outfield prospects Owen Caissie and Kevin Alcántara. After two straight seasons in which they went 83-79, the Cubs are in a much stronger position this year, but Hoyer and company need to deliver at this deadline.
Hired in November 2020, Minasian has had nearly five years to build the Angels into a contender, but hasn't been able to do it, and needs to start showing progress.
He has put together a strong young core of position players, led by shortstop Zach Neto, catcher Logan O'Hoppe, first baseman Nolan Schanuel and outfielder Jo Adell. However, on the pitching side of the equation, the Angels haven't improved during his tenure; this year, their major-league staff ranks 26th in ERA and 29th in WHIP. In addition, Minasian has needed to do a lot of patchwork-type transactions because the farm system just hasn't produced.
Minasian is signed through the 2026 season, but even with a year and a half left on his contract, there is no guarantee he'll be allowed to finish what is his second deal with the club. (He signed a two-year extension through 2026 in August 2024.)
This trade deadline is important for Minasian and the Angels regardless of what direction they decide to go: trying to buy and win now or (what I would do) looking to sell so they're stronger in the future. It might not even be his call, as Angels owner Arte Moreno could dictate the decision, but either way, the key goal Minasian must have is to improve their overall pitching in the short- and long-term at every level.
The Mariners' window to win a World Series won't stay open forever and the club must take advantage of its strong starting pitching and the MVP season of catcher Cal Raleigh. Seattle fans have been frustrated with the organization's lack of impact moves in the past, and that will only mount if it doesn't do enough to upgrade at the trade deadline.
Seattle is perhaps just one impact bat and one reliever away from having a legitimate chance to win the first World Series in franchise history. Ownership is willing to increase the payroll to make a big trade or two happen and Dipoto is willing to trade from the club's top-ranked farm system, which is loaded with trade bait.
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There can be no excuses this year. The Mariners must add those missing pieces and give themselves their best chance of winning it all since Lou Piniella managed the club to a 116-win season in 2001.
O'Hearn of the Orioles, Josh Naylor and Eugenio Suárez of the Diamondbacks, Luis Robert Jr. of the White Sox, and Kyle Stowers of the Marlins are among the big bat targets that make sense, and there are a number of available relievers who could fit the bill for Seattle. The Mariners have everything at their disposal to make trades, but the pressure is on to get deals over the line and this front office has to operate with urgency.
DeBartolo, whom the Nationals hired as interim GM earlier this month after firing president of baseball operations Mike Rizzo, has a relatively rare opportunity in this role to keep the job longer term, but that's likely only going to happen if he has a solid trade deadline.
In the offseason, the Nationals are expected to hire a new president to oversee both baseball and business operations, but that doesn't mean DeBartolo couldn't remain as the GM. He is not expected to trade any of the club's young core players in the coming days, instead probably trading around the edges of the roster, including the bullpen and bench, to pick up prospects. However, he could make a big impression if he goes outside the box and can land a haul for one of the core players not named James Wood or MacKenzie Gore.
It might make a lot of sense for the organization, if the right deal presents itself, and at the same time improve his chances of staying in the GM role long term. However, if DeBartolo's trade deadline is a dud, it could mean he never gets another opportunity in the big chair.
As a former GM, I'm rooting for him to be creative and make a name for himself by going big and bold at the deadline and helping expedite the Nationals' turnaround.
(Illustration: Will Tullos / The Athletic. Photos: Mike Elias: Diamond Images via Getty Images; Jed Hoyer: Michael Reaves / Getty Images; Ben Cherington: Mike Carlson / MLB Photos via Getty Images)