MLB Winter Meetings Winners, Losers: Best, Worst Deals From 2024 Event

MLB’s winter meetings never disappoint, but this season’s festivities might have been the best we’ve ever seen.

Dallas’ Hilton Anatole Hotel was home to not only the most lucrative agreement in the history of the sport but a trade that we’ve all been anticipating for months. The Boston Red Sox, New York Yankees and New York Mets the dominated conversation throughout the three-day sprint, landing huge names like Garrett Crochet, Max Fried and Juan Soto.

We all know this thing is a marathon, though, right?

Boston and New York certainly are home to the week’s biggest winners, but we’re going to get more specific than that while also highlighting some folks who probably are feeling some stress headed into the rest of the offseason:

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Winners

New York Mets
Juan. Soto.

Garrett Crochet
It’s probably the easy joke to make, but anyone who leaves the Chicago White Sox organization is a winner in our eyes. Crochet also happens to be joining a franchise in desperate need of top-end pitching talent, so he should walk in and be treated like a king.

The Red Sox also will want to get an extension done sooner rather than later, so it might not be long before the 25-year-old comes into a decent chunk of change, too.

Corbin Burnes
Burnes is the highest-profile pitcher who didn’t find a new home during the week, but that doesn’t mean he’s too stressed about the whole ordeal. Max Fried received a total of $218 million from New York. Crochet is on the periphery of an extension with Boston. Nathan Eovaldi got a fresh chunk of change from the Texas Rangers.

Burnes? He’s next.

The Toronto Blue Jays and San Francisco Giants are now left as the two most likely landing spots for the 30-year-old, who has seen his price tag do nothing but rise over the last couple of weeks.

Chase Meidroth
Boston probably wasn’t the best place to be for Meidroth, whose contact-first bat didn’t seem to be good enough for him to ever carve out a role in the infield. Rafael Devers, Triston Casas, Trevor Story, Kristian Campbell and Marcelo Mayer probably weren’t leaving any spots available.

Chicago, on the other hand? He might make the All-Star team if he puts together a decent enough batting average.

Alex Bregman
Bregman is still waiting on a new home, but he isn’t running out of options.

The Yankees, Red Sox, Houston Astros and Detroit Tigers are all still in the mix for the 30-year-old, who could play multiple positions for any one of them. It’s highly unlikely he will enter next season without a big, fat paycheck.

Losers

A.J. Preller
The San Diego Padres are cutting payroll, which means they’re reportedly listening to offers on the likes of starting pitcher Dylan Cease and infielders Luis Arraez and Xander Bogaerts — with outfielder Fernando Tatis Jr. also seemingly on the block.

Preller not only has to sit on the sidelines while all his friends (and/or enemies) throw around other people’s money, but he’s working the lines trying to get “value” for superstars. I’d feel bad if he wasn’t the guy who signed Bogaerts to such a ridiculous contract in the first place.

Teoscar Hernández
Hernández was supposed to find a home rather quickly following Soto’s deal, but as time continues to pass, the likelihood of him landing anything resembling a nine-figure deal seems to be waning.

The Red Sox haven’t been connected to him in almost a week, while the Blue Jays and Yankees seem to have shifted their attention elsewhere. The Dodgers are all that’s left, which isn’t just a boring outcome but one that could lead to less money for the 32-year-old.

Toronto Blue Jays
Toronto has missed out on Shohei Ohtani and Soto in back-to-back seasons, and seemingly can’t get any of the top starters to sign.

Hold this L.