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Five executives under the most pressure ahead of the 2023 MLB Winter Meetings

As the baseball world descends upon Nashville this weekend, some execs are feeling the heat more than others.

New York Yankees General Manager Brian Cashman looks on during batting practice prior to game four of the American League Championship Series against the Houston Astros at Yankee Stadium on October 17, 2019 in New York City. Photo by Mike Stobe/Getty Images

It’s been almost a month since the Texas Rangers captured the 2023 World Series, and Hot Stove season is finally set to really heat up. The baseball world will converge on Nashville this Sunday, Dec. 3, for the marquee event of the offseason: The Winter Meetings, in which teams and agents get together for four straight days of wheeling and dealing (and the occasional drink at the hotel bar).

We’ve seen a couple big names come off the board already in Aaron Nola and Sonny Gray, but a ton of talent remains available — including the most anticipated free agent in the history of the sport. There’s a strong chance that MLB’s landscape looks completely different this time next week; just look at last year’s Meetings, when Aaron Judge, Trea Turner, Justin Verlander, Xander Bogaerts and more put pen to paper. The stakes are high.

Of course, they’re a little higher for some executives than others. Who will land the final piece of their team’s World Series puzzle? Who will leave Nashville with a very unhappy fan base? Here are the five front offices feeling the most heat ahead of what promises to be a hectic few days.

MLB execs under most pressure ahead of 2023 Winter Meetings

Honorable mentions: Jerry Dipoto, Seattle Mariners; Mike Elias, Baltimore Orioles; Jed Hoyer, Chicago Cubs

For the first time since he got to Baltimore, offseason expectations are on Elias, who’s kept his powder dry in previous winters (and at this year’s trade deadline). He can ill-afford to stand pat again after watching his team get swept in the ALDS, though the O’s army of young talent certainly buys him some good will — and keeps him out of the top five here.

The Cubs announced their intentions as World Series contenders by poaching Craig Counsell from the division-rival Brewers. Now it’s on Hoyer to make good on that aggression, with Shohei Ohtani looming as the biggest prize. Dipoto, meanwhile, angered the entire Pacific Northwest with his “54 percent” comments at the end of the season, and nothing about his (and owner John Stanton’s) approach to the offseason so far suggests that the Mariners have the werewithal to take the big swing they so desperately need.

While Hoyer and Dipoto will both have questions to answer if they don’t make a splash in Nashville, however, both clubs have young cores in place that should set them up for success in the future. Things are a bit more perilous for the guys above them on this list.

5. Farhan Zaidi, San Francisco Giants

This isn’t just about the lack of on-field success, though missing the playoffs in two straight years — complete with an ugly second-half collapse in 2023 — certainly doesn’t help. More broadly, though, this is about a vibe shift: From Ohtani (the first time) to Bryce Harper to Aaron Judge to Carlos Correa, Zaidi has never been able to land the big fish during his time in San Francisco. The result is a team lacking any coherent identity, adrift in the sea of low-80s win totals. The Giants have been linked to everyone from Ohtani to Yoshinobu Yamamoto to Cody Bellinger, any one of whom would do wonders for turning this franchise’s narrative around. Strike out again, though, and Zaidi risks slipping into irrelevance — or being out of a job this time next year.

4. Ross Atkins, Toronto Blue Jays

It seemed like just yesterday that the Jays were set up for big things, ownership willing to spend around the dynamic young core of Bo Bichette, Vladimir Guerrero Jr., Alek Manoah and others. Flash forward a few years, though, and that core has still yet to win more than 92 regular-season games or even a single postseason series. Given the ugly way they went out in their Wild Card loss to the Twins this past October, the heat is on Atkins to figure out what this team needs to finally get over the hump (especially after he declined to fire embattled and unpopular manager John Schneider).

Item No. 1 will be fixing what’s been a weirdly inconsistent offense, one that now has holes to fill with Matt Chapman, Kevin Kiermaier and Brandon Belt all hitting free agency. Toronto has been one of the teams most heavily linked to Ohtani, and if Atkins manages to pull that off, they might just go ahead and elect him mayor. If the Jays swing and miss there, though, Atkins will have to pivot quickly in an uncertain position-player market if he hopes to avoid another disappointing season in 2024.

3. John Mozeliak, St. Louis Cardinals

Speaking of disappointing seasons: Arguably no team was more disappointing in 2023 than the Cardinals, who went from inner-circle World Series contenders to a last-place finish in the NL Central. The problem, put simply, was pitching: St. Louis’ rotation was awful last season, and the bullpen could use a boost too. Mozeliak has gotten a jump on that already, signing veterans Lance Lynn and Kyle Gibson to one-year deals, but this staff needs a lot more than sturdy back-end types. They need frontline talent, and a lot of it, if this team hopes to return to contention in 2024 — which it should, given its depth of position-player talent (and the fact that Nolan Arenado and Paul Goldschmidt aren’t getting any younger).

If Mozeliak lands, say, Blake Snell and Montgomery, the Cardinals could vault right back into the thick of the NL playoff picture. If he misses out, though, expect the angst level among the Best Fans in Baseball to ratchet up considerably.

2. A.J. Preller, San Diego Padres

Not only is Preller tasked with fixing a team that underachieved mightily in 2023, but he’ll have to do it with one hand tied behind his back: It’s an open secret around the league that Padres ownership is looking to slash payroll considerably (read: dozens of millions of dollars) ahead of next season.

The easiest way to make that happen would be to trade superstar outfielder Juan Soto, who’s set to make some $30 million in his final arbitration year before hitting free agency. Of course, trading Soto would also leave a gaping hole in a lineup that was already far too inconsistent in 2023. Can Preller split the difference, trimming fat for the future while giving Fernando Tatis Jr., Manny Machado and Xander Bogaerts the help they need to contend next season? If he doesn’t, he likely won’t be sticking around for the next Padres rebuild.

1. Brian Cashman, New York Yankees

No one does pressure quite like the Yankees, especially after missing the playoffs for the first time since 2016 — and flirting with a losing record for the first time in some 30 years. If you’d like to know whether Cashman is feeling the heat ahead of a pivotal offseason, just look at how defensive he’s gotten every time he’s spoken to the media in the last few months. Hal Steinbrenner appears to have far more patience than his father, but another year without postseason baseball would represent a five-alarm fire in the Bronx — one that could lead to far more change than we saw this season.

If Cashman wants to turn things around, it’ll likely start at these Winter Meetings, where completing a trade for Soto would go a long way toward fixing what was a moribund offense in 2023. Another outfielder on top of that wouldn’t hurt, as would at least one impact starting pitcher. There are a lot of holes here, is the point, and Cashman will have to show far more urgency than he has over the past few offseasons if he wants to plug them all.