Yankees, Astros: World Series or bust? 6 MLB front-office execs who need to win now

Eight weeks remain in MLB’s regular season. How they unfold will likely determine the fate of at least a few general managers and team presidents.

In an era of expanded playoffs, the pressure to make them is elevated. For a handful of MLB executives, the temperature surrounding their job security could be nearing a boiling point if their clubs aren’t successful in 2024. 

Neither what constitutes success nor the stakes are identical for each front-office leader identified below. But what they all have in common is they’re under fire and likely cannot afford a major letdown in the upcoming months.

Let’s examine six MLB executives who need to win now, along with what their respective clubs must accomplish this October, to get off the hot seat — if not keep their jobs.

Houston Astros 
Exec under fire: General manager Dana Brown
Club’s 2024 achievement floor: World Series appearance

Anything is possible for the members of the Astros front office after owner Jim Crane ended his three-year partnership with former general manager James Click following the Astros’ 2022 World Series championship. Crane’s unpredictable willingness to spend coupled with his front-office meddling has long put his GMs in difficult situations. It’s fair to wonder whether Brown’s job is safe if the Astros don’t win the pennant, let alone miss the playoffs entirely. (Entering Monday, they’re one game behind the Mariners for first in the AL West and five games out of a wild-card spot.) Since Crane didn’t hesitate to part ways with Click in the immediate aftermath of winning a title, what exactly does that mean for Brown as he tries to take Houston on another deep playoff run?

Brown is currently facing scrutiny for giving up so much for left-hander Yusei Kikuchi at the trade deadline. Adding even more pressure for Brown: The Astros’ window to win another World Series with their current core could be closing. Third baseman Alex Bregman will enter the open market after this season, and outfielder Kyle Tucker and starting pitcher Framber Valdez are set to hit free agency after the 2025 season, and it’s unclear whether either or both will be offered contract extensions before then. 

It’s fair to wonder how much autonomy Brown has had and who exactly is in charge in the Astros front office. In April, Reggie Jackson, a special advisor to Crane, said there are “four to five people that make decisions with the Astros.” Jackson noted Craig Biggio and Jeff Bagwell as part of that group, and we already know Crane plays an enormous role. Given all of that, Brown’s future with MLB’s most successful franchise over the past seven years seems tenuous at best.

New York Yankees 
Exec under fire: General manager Brian Cashman
Club’s 2024 achievement floor: World Series appearance

In his 26th season at the helm, Cashman is the longest-tenured GM in MLB. Across his quarter-century governing the Yankees front office, New York has made the postseason 21 times, including 14 consecutive years from 1998-2012, and won the World Series six times, with its most recent championship coming in 2009. Cashman has been under fire and receiving more scrutiny of late, particularly after the Yankees missed the playoffs last year for the first time in seven years, with Yankees fans even chanting “fire Cashman” in the Bronx last September for the roster he assembled. 

This year, the stakes are even higher than usual for Cashman and the Yankees due to the uncertain future of impending free-agent Juan Soto. While they have the generational Soto in the lineup, the Bronx Bombers are constructed to not only reach the playoffs, as is expected of them every year, but to finally get back to the World Series. It’s not as if fans, or the clubhouse, would be satisfied if the Yankees were eliminated (by the Astros) in the ALCS again, which has been the case three times in the past seven years. It seemed unlikely owner Hal Steinbrenner would dismiss his longtime GM after an injury-marred, mediocre 2023 season. Yet, it now seems plausible that Cashman’s roster has to reach the World Series not only to meet expectations, but to extend his run as the leader of the Yankees’ front office.

San Diego Padres 
Exec under fire: General manager A.J. Preller
Club’s 2024 achievement floor: NLCS appearance

Preller went all-in at the trade deadline and this past spring, trading away a dozen top prospects for star players who could help the win-now Padres play deep into October. Though they now boast the best bullpen in baseball, it remains to be seen whether the roster in its entirety has the talent necessary to defeat the Dodgers or Phillies in the playoffs. Anything is possible, and that’s certainly what Preller is thinking as San Diego gears up for an important stretch run.

Preller depleting the Padres’ farm system even more than it already was suggests he’s feeling the pressure to win big, or sayonara. After all, Preller has been asked about his job security all year. The topic of whether he’s truly on the hot seat, and whether he’s trying to save his job, has followed his every move. Will the Padres simply reaching the postseason, after failing to do so in 2023, be enough to save Preller? My guess is that it’s more likely San Diego must advance to the NLCS, like the club did in 2022, to solidify Preller’s future with the Padres. He took an enormous risk, and there’s plenty at stake for it to pay off.

San Francisco Giants 
Exec under fire: President of baseball operations Farhan Zaidi
Club’s 2024 achievement floor: Wild-card berth

The Giants have a top-10 payroll in MLB, and their record doesn’t justify it. They have been above .500 for just five days this season, and most of their top players haven’t lived up to expectations. Despite the obvious reasons for a new plan from Zaidi, he concocted a trade deadline that suggests they’re still somehow going for it in 2024. San Francisco has a 12.2% chance of clinching a wild-card spot, according to FanGraphs, and most Giants fans would agree that even that percentage is too high. 

Zaidi proclaimed the club has “the best rotation in baseball,” which has an outside shot at being true in the final two months of the season, but the team is still deeply lacking a playoff-ready offense. The Giants rank 19th in MLB in home runs, and no trade was made for a power hitter. They did the opposite, in fact, dealing away Jorge Soler just four months into a three-year deal in a salary dump. 

Zaidi, the Giants’ president of baseball operations since 2018, is facing mounting pressure to get the Giants back to the postseason. It looks like he’ll have to make good on that promise in order to keep his job, according to a July report from USA Today. That, at least, explains why Zaidi didn’t sell off major assets at the deadline. He listened to offers on reigning NL Cy Young winner Blake Snell, who threw a no-hitter in his most recent start for the Giants, but didn’t want to give up on the 2024 season. Zaidi has to hope that, at the very least, the Giants turn their season around enough to secure a wild-card appearance — or his unremarkable reign in San Francisco could be over.

Seattle Mariners 
Exec under fire: President of baseball operations Jerry Dipoto
Club’s 2024 achievement floor: Playoff appearance

Dipoto has led Seattle’s front office since the beginning of the 2016 season, and in that time, the Mariners have made the postseason just once, back in 2022. There was, of course, a rebuild at the onset of his tenure, and Seattle came out of it with a playoff-caliber roster and a farm system that is currently ranked 13th in the league, per FanGraphs. If those two elements are what ownership believe headline Dipoto’s front-office responsibilities, then it’s likely he’s not going anywhere. But a fan base that has yet to see its franchise make a World Series appearance is not happy about simply qualifying for the playoffs. It’s fair to question the overall expectations for management, and whether it’s enough for ownership to settle for a good core group that will sell jerseys and tickets. 

The Mariners were trending toward a wild-card berth last season before fizzling out in September, and they’re back in a similar position this year, vying for the AL West division title alongside the Astros. Dipoto traded for a power bat in Randy Arozarena and a veteran in Justin Turner, as well as adding relief help. Those additions could be enough to propel the Mariners to a wild-card or ALDS appearance, and while pitching has been a strength, their roster overall has yet to show it is on par with stronger AL contenders. The bottom line for Dipoto to avoid being on the hot seat is simply making the playoffs.

St. Louis Cardinals 
Exec under fire: General manager John Mozeliak
Club’s 2024 achievement floor: NLDS appearance

Mozeliak has been dropping hints all season that he, and his manager Oli Marmol, could be on the hot seat if the Cardinals don’t figure out a way to make the playoffs. Fans were understandably frustrated after St. Louis missed the postseason last year for the first time since 2018 and suffered its first losing season since 2007. The Cardinals are a storied franchise with annual expectations to be major players in October — not just fizzle out in the wild-card round like they have in their previous three playoff appearances. Now that the Cardinals are playing better baseball, and added a couple of reinforcements at the deadline, their floor should be to advance beyond a wild-card series. 

But is this roster and rotation good enough to even get that far? Mozeliak’s ability to turn an injured Tommy Edman into Erick Fedde and Tommy Pham was a good reminder of why he’s the second-longest tenured front-office leader in MLB. But the seat was already warm for the longtime president of baseball operations, and it will be scorching hot if the club fails to make the playoffs for the second straight year. As the playoff picture and their roster uncertainty currently stands, qualifying for the postseason is far from a guarantee for the Cardinals.

Deesha Thosar is an MLB reporter for FOX Sports. She previously covered the Mets as a beat reporter for the New York Daily News. The daughter of Indian immigrants, Deesha grew up on Long Island and now lives in Queens. Follow her on Twitter at @DeeshaThosar.

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