The MLB offseason often moves at a snail's pace, but that all changes when the Winter Meetings take place. The Winter Meetings are a four-day event held annually in December where executives from each MLB team, as well as some of the prominent free agents and agents, gather in the same hotel.
Given the fact that most of the prominent figures are all in the same place, transactions get completed. Often, star free agents sign during the week of the Winter Meetings, and we see trades get completed as well. With that in mind, here's a look at some of the biggest trades in Winter Meetings history since 2000.
Red Sox acquire Garrett Crochet from White Sox (2024)
Everybody knew that the Chicago White Sox would trade Garrett Crochet coming off an All-Star season with the team rebuilding, but nobody knew where the southpaw would end up. The Boston Red Sox got him in a Winter Meetings blockbuster, and let's just say that worked out quite well for them.
Acquiring Crochet was a bit risky as 2024 was his only full season as a starter and he had some durability concerns, but he was nothing short of dominant in 2025, leading the American League in innings (205.1) and strikeouts (255) while also dominating in his lone postseason start. Crochet was the AL Cy Young runner-up for Boston, and at just 26 years of age with several years of control on team-friendly money, there should be many more memorable seasons to come from this left-hander.
Boston Red Sox trade regrade: A
Losing Crochet hurts, but let's not act as if the White Sox got a bad return. Kyle Teel looks like a star catcher, Braden Montgomery is a top 35 prospect according to MLB Pipeline, Chase Meidroth has an excellent eye while playing steady defense at shortstop, and even Wikelman Gonzalez has some potential. The White Sox traded a Cy Young contender, so they lost the trade, but they still got back several worthwhile pieces.
Chicago White Sox trade regrade: B
Yankees win second Juan Soto trade sweepstakes (2023)
With his free agency looming a year later, it felt inevitable that the San Diego Padres were going to trade Juan Soto, knowing they didn't have the funds to keep him around long-term. The New York Yankees got him, and had as much success with him as they've had in over a decade.
Soto helped guide New York to the World Series and had arguably the best season of his career in pinstripes, hitting in front of Aaron Judge. Unfortunately, though, New York lost the Fall Classic and then had to watch Soto join their crosstown rivals, the New York Mets. An outstanding 2025 campaign from Trent Grisham helped mask the blow of losing Soto a bit, but trading all they did only for one year of Soto that didn't result in a World Series isn't the heist it would've been had he stuck around or had they won it all.
New York Yankees trade regrade: B+
The Padres made a similar kind of win-now push even after trading Soto and didn't even make it to the World Series. San Diego landed Michael King to bolster its rotation, and traded the top prospect in the deal, Drew Thorpe, to land Dylan Cease. They got some good results from both of these pitchers, but Cease signed with the Toronto Blue Jays and King is a free agent as well. Assuming King departs, the Padres traded a year of a generational talent in exchange for just one Wild Card Series win in two years. All that's left in San Diego from this deal, as of this writing, are Jhony Brito and Randy Vasquez, two mediocre pitchers. That's not what they wanted.
San Diego Padres trade regrade: B-
Yankees acquire reigning MVP Giancarlo Stanton (2017)
The Miami Marlins made the shocking decision to trade Giancarlo Stanton after winning the MVP award to the New York Yankees. Stanton rejected trades to the St. Louis Cardinals and San Francisco Giants, all but forcing his way to the Bronx, but the results haven't been quite as great as Yankees fans had hoped.
The idea of hitting Aaron Judge and Stanton back-to-back was frightening when this deal went down, but Stanton hasn't been the same player he was in that unforgettable year with the Marlins. He has never hit more than 40 home runs with New York, has never finished higher than 19th in the AL MVP balloting, and has only one All-Star appearance in eight seasons. To top it all off, Stanton is exclusively a DH at this point. Injuries have played a role, and his impressive postseason resume elevates the grade a bit, but the Yankees expected more than what they've gotten from Stanton when they got him.
New York Yankees trade regrade: B-
The only reason the Yankees' grade is higher than a C+ is that they traded virtually nothing to acquire him. Starlin Castro was a mediocre second baseman, and the two prospects they traded, Jorge Guzman and Jose Devers, combined for -0.6 bWAR for the Marlins. The Marlins got out of paying most of Stanton's deal, but didn't get much production at all in exchange for the reigning MVP winner and rarely reinvested what they saved into the team.
Miami Marlins trade regrade: D+
Red Sox beat Nationals to Chris Sale punch (2016)
Just a day after it appeared certain that Chris Sale was going to be pitching for the Washington Nationals, the Red Sox swooped in and acquired the White Sox star. In hindsight, this was the most lopsided Winter Meetings deal in recent memory.
The Red Sox got everything they could've wanted out of Sale, including a pair of top-five finishes in the AL Cy Young balloting and a World Series title. Injuries plagued him after inking an extension with the club, and the trade that sent Sale to the Atlanta Braves was a disastrous one, but when looking at what Sale accomplished in Boston and what the Red Sox gave up to get him, this was such a heist.
Boston Red Sox trade regrade: A
At the time, it looked like the White Sox had done well. Yoan Moncada was MLB Pipeline's No. 1 overall prospect at the time, and fireballer Michael Kopech was one of the league's top pitching prospects. Unfortunately, the results were disastrous. Moncada never came close to reaching his potential in six injury-riddled seasons on the South Side, and the same can be said of Kopech, who struggled in parts of five injury-riddled seasons. As for Victor Diaz and Luis Alexander Basabe, Diaz never made it past High-A, and Basabe only made it to the majors with the San Francisco Giants and played in 20 games during the shortened 2020 season.
Chicago White Sox trade regrade: F
Diamondbacks gift Dansby Swanson to Braves (2015)
Just days after signing Zack Greinke, the Arizona Diamondbacks beefed up their rotation even more by trading for Shelby Miller, a young All-Star. Acquiring Miller meant they had to part with a lot, though, and boy, do the Diamondbacks regret making this deal in hindsight.
The Atlanta Braves received Dansby Swanson, the No. 1 overall pick from the 2015 MLB Draft, as well as Ender Inciarte, a soon-to-be three-time Gold Glover. Inciarte was a mainstay in Atlanta's outfield for several years, but Swanson was the big prize. It took him a while to adjust to big league pitching, but once he did, Swanson was a key cog on an eventual World Series-winning team. He might've only been a one-time All-Star in Atlanta, but his value to that team was far greater than just looking at the basic stats. Some thought the Braves would've won this deal given Swanson's tremendous upside, but Miller's struggles in Arizona made it a clear fleece.
Atlanta Braves trade regrade: A-
In the 29 games he appeared in for the Diamondbacks in his first stint in Arizona, Miller posted a 6.35 ERA. Yes, it was that bad. He went from being an All-Star to simply uncompetitive in Arizona. To make matters even worse, Gabe Speier, a solid reliever now, never appeared in a big league game for Arizona. They got -1.2 bWAR from this deal in exchange for Swanson and Inciarte. Not great!
Arizona Diamondbacks trade regrade: F
Max Scherzer, Curtis Granderson headline three-team deal (2009)
The lone three-team deal on this list is an absolute doozy in hindsight. If we're being honest, all three teams on this list benefited somewhat. Still, there is a pretty clear winner and one very clear loser when re-grading this deal.
The Tigers are clear winners, as they acquired four of the seven players dealt, headlined, of course, by Max Scherzer. The future Hall of Famer won a Cy Young award in his fourth of five years in Detroit and helped lead the team to a World Series the following year. Austin Jackson was a solid center fielder for a while, then was part of a deal that sent David Price to the Motor City. Even Phil Coke and Daniel Schlereth are two left-handed relievers who had some decent years in Detroit. They did give up a great player in Curtis Granderson, but acquiring Scherzer and Jackson, a pair of young, unproven players who wound up doing great things in Detroit, makes it a clear win.
Detroit Tigers trade regrade: A
The Yankees are another winner of this deal. They didn't get a future Hall of Famer, but Curtis Granderson made two All-Star teams and had a pair of 40+ home run seasons in the Bronx. Granderson was the most established player in this deal, and yet, the Yankees weren't the team that traded Scherzer. They parted with Austin Jackson, Phil Coke and Ian Kennedy, so it's not as if they got Granderson for free, but this was still good value for them.
New York Yankees trade regrade: A-
The Arizona Diamondbacks are clear losers in this deal. To be fair, they didn't get nothing. Ian Kennedy finished fourth in the NL Cy Young balloting a couple of years after this deal went down and was a servicable arm for them for a while, but the Diamondbacks only got one lousy season out of Edwin Jackson. Getting Kennedy makes the idea of trading Scherzer a bit easier to come to terms with, but not really.
Arizona Diamondbacks trade regrade: C-
Tigers acquire Miguel Cabrera from Marlins (2007)
The earliest trade on this list might be the most memorable one. The Florida Marlins sent Miguel Cabrera and Dontrelle Willis, two established stars at the time, to the Tigers in exchange for six players. Unfortunately, the Marlins learned the hard way that quality is always more important than quantity. Getting six players for two doesn't guarantee you anything.
The Tigers got everything they could've asked for out of this deal. Sure, Dontrelle Willis never wound up pitching well or much for Detroit, but landing Cabrera was good enough. Cabrera spent the last 16 years of his career with Detroit and will soon find his way to Cooperstown with a Tigers cap on. It's virtually impossible to lose a trade that leads to 16 years of a future Hall of Famer, but the Tigers won this deal very handily.
Detroit Tigers trade regrade: A+
Andrew Miller, the biggest name in the deal, had his best years roughly a decade after this deal was completed with Cleveland. Cameron Maybin, the other huge name in the deal, never spent a full year in the majors before getting traded to the San Diego Padres three years later. Burke Badenhop was the only player who somewhat lived up to his potential, and he was never anything more than a solid reliever. Yeah, this was a disaster for the Marlins no matter how you slice it.
Florida Marlins trade regrade: D-
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