The biggest Winter Meetings trades of all time

The Winter Meetings mark the most unpredictable days on the offseason calendar, and through the decades we've seen the tides of the game shift repeatedly with some massive trades.

On Wednesday, we saw one of the game's most electric starting pitchers, Garrett Crochet, sent from the White Sox to the Red Sox for a significant prospect package. With that in mind, here is a look at some of the biggest swaps in Winter Meetings history, featuring a multitude of Hall of Famers and Hall of Famers-to-be:

2024: Red Sox get their rotation ace in Crochet
Garrett Crochet turned himself into a frontline starter during a breakout 2024 season that featured 209 strikeouts in 146 innings and his first All-Star selection. However, with him two years away from free agency and with the White Sox in the middle of a lengthy rebuild following a record-setting 121-loss season, Crochet didn't really really fit in Chicago's long-term plans.

But he was a perfect fit for Boston. The Red Sox entered the offseason with their sights set on upgrading a rotation that lacked a left-hander as well as a bona fide No. 1 starter. With Crochet, they found someone who could address both areas. The Red Sox used their position-player-heavy farm system to bring Crochet to Boston, sending four prospects to the Windy City. That included their top Draft picks in 2023 (catcher Kyle Teel) and '24 (outfielder Braden Montgomery). Both of those players were ranked among MLB Pipeline's Top 100 prospects at the time of the deal. Boston also included infielder Chase Meidroth and right-handed pitcher Wikelman Gonzalez in the deal to get its much-needed ace.

2023: Bombers bring Soto to the Bronx
Sixteen months after being traded from the Nationals to the Padres at the 2022 Trade Deadline, Juan Soto found himself involved in another blockbuster, this one sending him and center fielder Trent Grisham to the Yankees for Michael King, Drew Thorpe, Jhony Brito, Randy Vásquez and Kyle Higashioka.

Trade talks between the Yanks and Padres reportedly stalled the weekend before the Winter Meetings in Nashville, with New York balking at San Diego’s lofty asking price for Soto, a player with only one year of team control remaining before free agency. However, the two sides resumed discussions at the Winter Meetings and eventually reached a deal. The trade gave the Bronx Bombers the superstar left-handed bat they were seeking and provided the Padres with payroll relief, as well as some much-needed pitching help.

The Padres would soon send Thorpe to the White Sox as part of a package for right-handed starter Dylan Cease, who had a strong 2024 season in San Diego. Meanwhile, Soto had a monumental year. After hitting a career-best 41 homers, finishing third in the AL MVP voting and leading the Yankees to the World Series, Soto agreed to a record-setting 15-year, $785 million contract with the crosstown Mets during that year's Winter Meetings.

2017: Reigning NL MVP heads to AL
This deal was first reported on the eve of the Winter Meetings in Orlando, Fla., and became official on the first weekday of the event -- that Monday. Giancarlo Stanton's 59-homer season had netted him NL MVP honors, but he had just completed the third year of his 13-year, $325 million contract, and Marlins ownership had expressed a desire to shed payroll.

The Marlins sent him to the Yankees for Starlin Castro and Minor Leaguers Jose Devers and Jorge Guzman. Stanton became just the third reigning MVP to change teams in the offseason, joining Alex Rodriguez and Barry Bonds. He hasn't reached the same heights again in the Bronx, although he has topped the 30-homer mark three times.

2016: Sale swaps his Sox
A day after rumors had the White Sox nearing a deal to send Sale to the Nationals, Chicago shipped him to Boston instead. The Red Sox, who already had David Price and 2016 AL Cy Young Award winner Rick Porcello, further solidified their rotation with a 27-year-old superstar under club control for three more seasons at a reasonable price. But they also had to reach into their highly touted farm system to do it.

For parting with Sale, the White Sox landed four of the Red Sox's top 30 prospects, according to MLB Pipeline, including five-tool infielder Yoán Moncada (No. 1) and hard-throwing right-hander Michael Kopech (No. 5). Moncada, also the top overall prospect in baseball, got the highest bonus in history for an amateur player ($31.5 million) when Boston signed him in 2015, after he left Cuba. But Sale finished in the top four of AL Cy Young Award voting in both 2017 and '18 and got the last out of the World Series in the latter season.

2015: Historic trade for No. 1
Fresh off signing starter Zack Greinke to a six-year deal worth more than $200 million, the D-backs decided to commit fully to their newfound "win now" approach at the 2015 meetings in Nashville. The D-backs sent three players to the Braves, including shortstop prospect Dansby Swanson, whom they had drafted No. 1 overall not six months prior, as well as 2016 Gold Glove-winning outfielder Ender Inciarte, for a package highlighted by All-Star starter Shelby Miller.

Swanson became the first top overall pick to be traded before reaching the Majors since Adrian Gonzalez in 2003 and the first ever to be dealt the year he was drafted. Miller posted a 6.15 ERA in his first year in Arizona as the D-backs lost 93 games, and he went on to make only 29 appearances while battling injuries during his three-season tenure with the club. Swanson became a stalwart in Atlanta, helping the club win the World Series in 2021 before signing with the Cubs in December 2022.

2009: Three-team stunner
The D-backs, Tigers and Yankees pulled off a three-team trade at the 2009 Winter Meetings in Indianapolis. In a fairly uncommon occurrence, the deal actually benefitted each team involved in some way. The D-backs received Edwin Jackson and Ian Kennedy, the latter of whom played the role of ace during Arizona's 2011 National League West title run. The Yankees, meanwhile, hauled in Curtis Granderson, who hit 115 homers in four seasons in the Bronx and earned a fourth-place AL MVP Award finish in 2011.

Still, several years later, it's safe to say the Tigers probably won this deal. Detroit landed Max Scherzer and Austin Jackson (along with Daniel Schlereth and Phil Coke). Jackson was a very solid center fielder for five seasons in Detroit, but Scherzer ended up being the biggest difference-maker. He established himself as one of the game's top pitchers, winning the 2013 AL Cy Young Award and averaging 241 strikeouts over his final three seasons with the Tigers.

2007: Miggy lands in Detroit
It's easy to think of Miguel Cabrera as the cornerstone of the Detroit Tigers, but he was a superstar well before he headed to the Motor City. In five seasons with the Marlins, Cabrera hit .313 with 138 homers and made the All-Star team four times.

Then, at the Opryland during the 2007 Winter Meetings, Dave Dombrowski swung a huge deal, sending six players, including Andrew Miller and Cameron Maybin, to the Marlins for Cabrera and Dontrelle Willis. The rest, of course, is history. Cabrera developed into arguably the best hitter of his generation and finished out his career in Detroit.

1990: Padres and Blue Jays pull off a blockbuster
According to The New York Times, then-Blue Jays general manager Pat Gillick called his wife Doris during the 1990 Winter Meetings, telling her he had just dealt Fred McGriff and Tony Fernandez to the Padres for Joe Carter and Roberto Alomar. Her response: "Will you get home before you screw up the team any further?"

Of course, with the benefit of hindsight, Pat made out just fine in the trade. Alomar went on to a Hall of Fame career, and Carter won the 1993 World Series with his famed walk-off home run in Game 6. Both played an integral role on Toronto's only two championship teams. San Diego, on the other hand, got a few very quality years out of McGriff and Fernandez.

1984: Rickey lands in the Bronx
The 1984 Winter Meetings in Houston saw a future Hall of Famer in Rickey Henderson on the move. The Yankees sent Tim Birtsas, Jay Howell, Stan Javier, Eric Plunk and Jose Rijo to the A's in exchange for Henderson, who swiped 326 bags and recorded 663 hits in five seasons for the Bombers.

Only Derek Jeter (358) has recorded more stolen bases in pinstripes, and he did so with the benefit of 2,151 more games than Henderson. The Yanks eventually sent Rickey back to Oakland in 1989, and he broke the all-time stolen-base record two years later.

1984: Gary Carter to the Mets
Murray Cook's first task as general manager of the Montreal Expos was to trade beloved catcher Gary Carter -- an order that was given by Expos owner Charles Bronfman during the 1984 offseason. As the story goes, Cook and Mets executive Frank Cashen came to an agreement on the trade in a stairwell at the Opryland.

In exchange for Carter, New York gave up Hubie Brooks, Mike Fitzgerald, Herm Winningham and Floyd Youmans. Carter spent five seasons of his Hall of Fame career with the Mets, making the All-Star team four times and playing a pivotal role on the 1986 club that won the World Series.

1980: Herzog rebuilds the Redbirds
Whitey Herzog had served as the Cardinals' interim manager for 73 games before he was promoted to the club's general manager in August 1980. That offseason, Herzog took the manager spot back from Hall of Famer Red Schoendienst and immediately made his mark in his front office role for St. Louis.

Herzog engineered three massive trades, featuring 23 total players, and wound up sending a dozen Cardinals players away. When the dust had cleared, Herzog had one elite reliever in Bruce Sutter but sent another, Rollie Fingers, to the Brewers alongside Ted Simmons and Pete Vuckovich. While Herzog sent away those three stars, his moves in 1980 set the groundwork for later deals that would bring Lonnie Smith, Ozzie Smith and other valuable pieces to a club that captured a pair of National League pennants in the 1980s. In fact, the Redbirds wound up defeating the Brewers in the World Series just two years later.

1975: Bill Veeck is "Open for Business"
During the 1975 Winter Meetings in Fort Lauderdale, Fla., newly minted White Sox owner Veeck famously set up a table in the hotel lobby with a sign that read "Open for Business." He then went on to make six trades involving 22 players, including Jim Kaat (to the Phillies), Clay Carroll (to the White Sox from the Reds), Ralph Garr (to the White Sox from the Braves) and Dick Ruthven (from the Phillies to the White Sox, then from the White Sox to the Braves).

The South Siders won 75 games during the 1975 season, so Veeck's approach made at least some sense. But the deals didn't pay off, and the White Sox finished last in the AL West in '76 with just 64 victories.

1965: Frank Robinson goes to Baltimore
Legendary baseball executive Lee MacPhail left the Baltimore Orioles after the 1965 season, but not before he set in motion a trade that would shape the course of baseball history. At the '65 Winter Meetings, MacPhail negotiated the deal with the Reds that sent Frank Robinson to the Orioles for Jack Baldschun, Milt Pappas and Dick Simpson.

Robinson would go on to win two World Series and the 1966 American League MVP Award in Baltimore. Before completing the deal, however, MacPhail first made sure to get the approval of Harry Dalton, the incoming general manager. Fortunately for O's fans, Dalton signed off.

1959: Yankees acquire Roger Maris
The Kansas City Athletics' disappointing 1959 season culminated with the firing of manager Harry Craft. After being let go, Craft allegedly told Yankees skipper Casey Stengel to trade for A's youngster Roger Maris, because he was destined for stardom.

Sure enough, at the Winter Meetings in Miami Beach, Fla., Stengel followed through, landing Maris in exchange for Don Larsen, Hank Bauer, Norm Siebern and Marv Throneberry (New York also received Joe DeMaestri and Kent Hadley). Two years later, Maris became baseball's single-season home run king, and he helped lead the Yanks to World Series appearances in each of the next five years -- including two titles.