MLB 2024 winter meetings: Winners, losers and takeaways

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Heading into the MLB winter meetings each year, there is always hope for a big week of free agent signings and trades. The 2024 meetings delivered.
Top free agent Juan Soto chose the New York Mets for 15 years and $765 million, the largest contract in baseball history. The New York Yankees responded to losing Soto by handing a record deal to left-handed starter Max Fried. Not to be left behind in the American League East, the Boston Red Sox landed lefty ace Garrett Crochet in a trade with the Chicago White Sox.
We asked our MLB experts who were on the scene in Dallas to break down everything that happened this week. Which moves most impressed them? Which moves most confused them? Who were the biggest winners and losers? And what can we expect next?
What was your favorite move of the winter meetings?
Jorge Castillo: Garrett Crochet going to the Boston Red Sox made the most sense all along. It wasn’t a matter of if but when the Chicago White Sox would finally trade Crochet for position player talent. On the other end, Boston’s top offseason priority was adding a front-line starter and the Red Sox had a surplus of position player prospect capital. Both teams got what they wanted when they executed the trade — Crochet for four prospects — on Wednesday. It was the perfect match.
Alden Gonzalez: Soto spurned them for the Mets and Fried spurned them for the Yankees, but the Red Sox countered by acquiring the most sought-after pitcher in the trade market. And though it cost four highly-regarded prospects to land Crochet from the White Sox, the Red Sox did well in plucking from a deep pool of position-player prospects to grab a high-end starter who’s controllable for two years and will cost a fraction of what far lesser pitchers commanded in free agency. Better yet, they also freed up money to heavily pursue the likes of Alex Bregman and Teoscar Hernandez, if they so choose. The Red Sox have more business to conduct, of course, but this was a crucial pivot.
Buster Olney: One of the greatest hitters we’ve ever seen got the biggest contract ever bestowed, so the Mets win the prize. But since the Willy Adames deal wasn’t announced until the middle of the meetings, I can pick that. Buster Posey presented his vision of what he wanted for the San Francisco Giants moving forward and made it clear he’s seeking ballplayers who fans will enjoy, and Adames fits that description. He’s a good player, a good defender, someone who can move to another spot as he ages, but his love for the game is apparent. That’ll translate in a market that has been starved for star players.
Jeff Passan: Even if the price on Soto was exorbitant, Steve Cohen has the money, wants to spend it and got a Hall of Famer in the process. Crochet, also at a high cost in prospects, is precisely who the Red Sox needed. But for the combination of need and fit, Nathan Eovaldi’s return to the Texas Rangers on a three-year, $75 million contract was imperative as they try to shake off the disappointment of 2024 and rekindle the World Series-winning 2023 version of themselves. With Jacob deGrom and Tyler Mahle healthy and Kumar Rocker showing front-line-starter stuff in his September cup of coffee, adding Eovaldi — a tremendous worker and clubhouse presence — makes the Rangers’ rotation dangerous. In a wide-open AL West, Texas could enter the season as the favorite.
Jesse Rogers: The Yankees’ pursuit of Soto. Even though they lost out on him, they drove up the price on the Mets and then took that money and signed Max Fried while continuing to pursue other top players. If they add first baseman Christian Walker and trade for Cody Bellinger — all with the money they saved on Soto — then who is to say the Yankees aren’t better without him? By the way, how do we know that wasn’t the Yankees’ strategy the whole time, knowing that Mets owner Steve Cohen would stop at no lengths to get the best player on the market. Either way, the Yankees are going to come out of the winter looking just fine.
What one move had you scratching your head?
Castillo: Andres Gimenez’s offensive production regressed over the past two seasons since a breakout 2022 All-Star campaign and he qualified as expensive for the Guardians. But seeing Cleveland trade him was a stunner. Gimenez is one of the best defenders in the sport and doesn’t turn 27 until September. The Guardians signing him to a seven-year, $105 million extension — the second-largest expenditure in franchise history — on the eve of Opening Day in 2023 signaled that he was one of their core players. Instead, he was moved north.
Gonzalez: Alex Cobb’s one-year, $15 million deal with the Detroit Tigers. It’s only a one-year deal, and it makes sense for a Tigers team that can’t chase the high-end starting pitchers and needed a veteran to help round out a young group. But Cobb securing $15 million as a 37-year-old coming off a three-start season — one in which he recovered from hip surgery, dealt with shoulder inflammation, navigated through a blister and was ultimately ruled out because of a back strain — spoke to the inordinate sums commanded by starting pitchers in this market.
Olney: The Mets signing Clay Holmes with the intent of shifting him to the rotation is confusing. Holmes is highly respected, a good teammate and hopefully it works out, but it’s safe to say there is a lot of skepticism around the sport that this is going to translate, given his struggles to consistently throw strikes. Jeremy Hefner is an excellent pitching coach, one of the best, and maybe he can help Holmes the way that he helped Luis Severino, Sean Manaea and Jose Quintana, but this is a hell of a gamble, given the Mets’ need for starting pitching.
Passan: The Dodgers giving Michael Conforto a one-year, $17 million deal was the epitome of luxury. Already far over the competitive-balance-tax threshold — and, as a multitime offender, needing to pay a 110% tax on every dollar spent over $301 million — Conforto will cost even more. Clearly the Dodgers believe he can be a force in their lineup. And after winning the World Series, Los Angeles warrants the benefit of the doubt. This isn’t the typical head-scratching move because it’s bad as much as it was simply unexpected.
Rogers: I mean it’s not my money, but the Mets paying Soto as much as they did seems ludicrous. He can bat only one time through the order. Then again, $765 million to Steve Cohen might be like $165 million for anyone else. As long as it doesn’t hamper them for — I don’t know — the next 15 years, more power to them. But that amount is the definition of a head scratcher.
Who is the most interesting available player who didn’t sign or get traded this week?
Castillo: Corbin Burnes, Max Fried, and Blake Snell were widely considered the three best starting pitchers available in free agency, and only Burnes remains without a team. It has become a game of musical chairs. With Fried going to the Yankees, Snell to the Dodgers and Crochet to the Red Sox via trade, the Blue Jays and Giants are the two teams that stand out as clubs in the market for an ace that haven’t landed one. Burnes is likely to beat Fried’s massive deal — eight years for $218 million — perhaps venturing into Stephen Strasburg (seven years for $245 million) territory.
Gonzalez: The emergence of Kyle Tucker as a trade candidate has been fascinating — as has the Yankees’ reported interest in him. Yankees fans will gladly settle for Fried and Tucker as consolation prizes for not landing Soto, especially if Walker also joins them. Some would even prefer it. But other teams are undoubtedly in play for Tucker. The Astros can’t afford to bring back Bregman back on the type of deal he wants and sign Tucker as a 28-year-old free agent next offseason. Trading him, even though he’s controllable for only one year, would bring back the type of prospect package that would go a long way toward replenishing the upper levels of an Astros system that has dried up. But it will hurt the 2025 team fairly significantly. And it would be a huge risk for the Astros to deal Tucker before knowing they can bring back Bregman. The guess is that won’t happen.
Olney: I’m really curious about the next landing spot for Walker Buehler, because we’ll know how teams have treated Buehler’s strong postseason performances — as outliers, or as a sign of a pitcher transitioning from pure power into someone who can beat great hitters with his pitch mix. Late in the regular season, it was widely assumed in the industry that Buehler’s best play was to take a short-term deal in 2025, then demonstrate that he’s healthy and capable of adjustments — and yet in just a few weeks of the postseason, he proved a lot, executing all of his pitches. Somebody is going to invest in the guy who won Game 3 of the World Series as a starter before closing out Game 5.
Passan: Even though the earliest he can sign is Jan. 15, Roki Sasaki will be at the forefront of teams’ minds into the new year. Just look at the price of pitching. Blake Snell got more than $30 million a year. Max Fried got $27.25 million for eight years. Nathan Eovaldi got $25 million, Luis Severino $22.3 million, Yusei Kikuchi $21 million, Frankie Montas $17 million. To get a potential front-line pitcher like Sasaki for anywhere between $5 million and $7.5 million and have him playing at the major league minimum for the next three seasons is a coup. And whichever franchise is lucky enough to land him will be even more thankful for the relative value he brings.
Rogers: Bregman. He could be a domino for other players — plus, the idea of him leaving the Houston Astros for, say, their archrivals, the Yankees, is juicy. Or is there another move to be made? Maybe the Philadelphia Phillies get involved if they trade Alec Bohm. Detroit would be flexing some muscle if he signs there. Or perhaps the heart strings get a tug and Houston owner Jim Crane says yes to whatever agent Scott Boras is proposing and the Astros keep the band together. Bregman comes with an instant championship résumé. Whether he takes his services elsewhere is something to watch.
Who was the biggest winner — and loser — of the week?
Castillo: The biggest winner is the guy who secured the largest contract in professional sports history. But since naming Juan Soto was obvious, let’s go with a secondary winner: Scott Boras. A year ago, the superagent was criticized for how he handled the free agencies of some of his high-profile clients. Now he’s back landing deals for more money than projected, none bigger than Soto’s massive commitment. On the other side, the losers of the week are the Orioles. They’re not expected to compete to re-sign Burnes and they watched the Red Sox dip into their position player prospect capital for Crochet — something the Orioles could’ve done. Competing for an AL East title without an ace will not be easy. The O’s must find one.
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Gonzalez: Let’s not complicate this — the biggest winners are the Mets. They landed the biggest star and showed the rest of the industry that nobody can compete with them financially when Steve Cohen zeroes in on a target. Also, they’re not done adding. The next decade of baseball in Queens will be a lot of fun, and this week solidified that. The biggest losers? The small- to mid-market teams that clearly can’t compete for the types of contracts that Soto and Fried received and Burnes will eventually land. The gap between the haves and have-nots is perceivably widening, illustrated by the common theme shared by the five teams that were legitimately in on Soto: They all have stable media contracts. At least for now.
Olney: Mets. We anointed the Mets the winner of the offseason about four weeks ago, because you knew they were going to be aggressive and make bold moves — and they landed a future Hall of Famer who just turned 26. Nobody’s going to beat that this winter.
Passan: Everyone else wants to say Juan Soto? Fine. That’s the right answer. But how about Max Fried? He landed the largest guarantee ever for a left-handed pitcher and the second-longest contract for a domestic free agent pitcher in baseball history. Now Fried gets to pitch for the Yankees and join a team coming off a World Series appearance. The losers are the Toronto Blue Jays, who are the only team that tried for Shohei Ohtani and Juan Soto in free agency and whiffed on both. As the great Ricky Bobby said, if you ain’t first, you’re last.
Rogers: Um, Soto? Does he really deserve more than Shohei Ohtani? He’s the winner by a mile. The biggest losers are the Miami Marlins, who unloaded a young power hitter in Jake Burger — one of the few interesting players on their team — for three prospects who won’t help them anytime soon. The best of those prospects wasn’t even one of the Texas Rangers’ better minor leaguers.
Which team is now under the most pressure to do something big after the meetings?
Castillo: The Toronto Blue Jays have money to spend and they want to spend it, but they just can’t get anyone to take it. At least not yet. The pressure is on to improve the roster one year before Vladimir Guerrero Jr. hits free agency.
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Gonzalez: A rival GM posed this question earlier this week, as free agent starters were coming off the board and prices continued to seem high: What, exactly, are the Baltimore Orioles going to do with their rotation? They clearly need help there but have yet to make any moves — in a division where the Yankees and Red Sox are being aggressive and even the Blue Jays, still unable to reach an extension with Guerrero, continue to try to supplement their current group. The Orioles’ deep crop of young position-player stars has their contention window wide open — but they need to support it with pitching.
Olney: The Orioles are right in the middle of their window to win, after making the playoffs the past two years, and yet they continue to take half-measures in addressing their desperate need for pitching. Look, the Cubs really weren’t in position to win until they gave Jon Lester $155 million after the 2014 season, and the Astros turned the corner when they made the aggressive move for Justin Verlander in the summer of 2017. The Orioles took on a one-year rental in Burnes last year, knowing he was going to walk away at season’s end, and added Zach Eflin before the 2024 trade deadline, but they needed more; the players and fans deserve more. Is this about the front office? Is this about the ownership not willing to pay for high-end pitching? Does it matter, because either way, the clock is ticking and soon enough, idiots like me will be writing about when the Orioles will have to consider trades of their incredible core position players before they approach free agency.
Passan: It’s still the Red Sox. They’re carrying a middle-of-the-pack payroll, and while Crochet’s value is as much in his deflated arbitration salary as his immense talent, his acquisition leaves plenty of room for Boston to pursue Corbin Burnes or Alex Bregman. It should, of course, be Burnes and Bregman, but the Red Sox’s pullback from the elite-payroll club — they had the highest salaries in MLB in 2018 and 2019 — to this version of themselves makes that highly unlikely. If Boston emerges with either, consider it a win.
Rogers: The Red Sox would have been the easy answer, but they got on the board by acquiring Crochet from the White Sox for four prospects. It’s time for the Atlanta Braves to get active as they lost Fried to the Yankees and have holes on the mound to fill. (Plus, the Mets just got a whole lot better in the Braves’ division.) Houston seems like a close second to Atlanta.

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