Ranking MLB's Top 10 Winter Meetings Trades Ever
The annual MLB winter meetings kick off on Monday from Orlando, Florida, and with it comes a whirlwind of activity, whether it's actual deals getting done or simply a wave of new rumors and speculation to dissect.
Last year, Juan Soto signing a record-breaking contract with the New York Mets was the biggest storyline of the winter meetings, while Willy Adames also inked a nine-figure deal with the San Francisco Giants.
It also brought a massive blockbuster trade, as the Boston Red Sox found their ace when they acquired Garrett Crochet from the Chicago White Sox for a package of prospects built around their two most recent first-round picks in Kyle Teel and Braden Montgomery.
Ahead of this year's meetings, we've taken a look back at the top 10 trades in winter meetings history, with more than a few Hall of Famers on the list.
Honorable Mentions
1 of 11
Dec. 12, 1980: Brewers acquire RHP Rollie Fingers, C Ted Simmons, RHP Pete Vuckovich from the Cardinals for OF Sixto Lezcano, RHP Lary Sorensen, LHP Dave LaPoint, OF David Green
Dec. 10, 1982: Astros acquire RHP Mike Scott from the Mets for OF Danny Heep
Dec. 5, 1984: Yankees acquire OF Rickey Henderson from the Athletics for RHP José Rijo, RHP Eric Plunk, OF Stan Javier, RHP Jay Howell, LHP Tim Birtsas
Dec. 6, 1989: Cleveland acquires C Sandy Alomar Jr., 2B Carlos Baerga, OF Chris James from the Padres for OF Joe Carter
Dec. 15, 1997: Padres acquire RHP Kevin Brown from the Marlins for 1B Derrek Lee, RHP Rafael Medina, LHP Steve Hoff
Dec. 9, 2015: Diamondbacks acquire RHP Shelby Miller, LHP Gabe Speier from the Braves for SS Dansby Swanson, OF Ender Inciarte, RHP Aaron Blair
Dec. 11, 2017: Yankees acquire OF/DH Giancarlo Stanton from the Marlins for SS Starlin Castro, SS José Devers, RHP Jorge Guzmán
Dec. 14, 2017: Cardinals acquire OF Marcell Ozuna from the Marlins for RHP Sandy Alcantara, RHP Zac Gallen, OF Magneuris Sierra, LHP Daniel Castano
Dec. 7, 2023: Yankees acquire OF Juan Soto, OF Trent Grisham from the Padres for RHP Michael King, C Kyle Higashioka, RHP Randy Vásquez, RHP Drew Thorpe, RHP Jhony Brito
Dec. 11, 2024: Red Sox acquire LHP Garrett Crochet from the White Sox for C Kyle Teel, OF Braden Montgomery, IF Chase Meidroth, RHP Wikelman González
10. Johan Santana to the Minnesota Twins
2 of 11
Date: Dec. 13, 1999
Transaction: Twins acquire LHP Johan Santana from the Marlins for RHP Jared Camp
It's not uncommon for a team to select a player in the Rule 5 draft, then immediately flip him to another team for cash or a different prospect, but more times than not those deals end up being of little consequence.
In 1999, it was one of those deals that saw a young left-hander named Johan Santana plucked from the Astros organization by the Marlins, then swiftly traded to the Twins for right-hander Jared Camp who never ended up reaching the majors.
After struggling to a 6.49 ERA in 86 innings as a rookie, Santana eventually emerged as one of the most dominant pitchers of his era. He took home AL Cy Young honors in 2004 and 2006 while winning two ERA titles and three strikeout titles during an elite four-year peak.
9. A Massive 3-Team Blockbuster
3 of 11
Date: Dec. 8, 2009
To DET: RHP Max Scherzer (via ARI), OF Austin Jackson (via NYY), LHP Phil Coke (via NYY) and LHP Daniel Schlereth (via ARI)
To NYY: OF Curtis Granderson (via DET)
To ARI: RHP Edwin Jackson (via DET), RHP Ian Kennedy (via NYY)
The prize of this massive three-team trade at the time was Curtis Granderson, who went on to log a pair of 40-homer, 100-RBI seasons during his four years with the Yankees.
Edwin Jackson and Ian Kennedy were both promising young starters who stepped immediately into the D-backs rotation, but it was the Tigers who won this deal in hindsight by acquiring a young Max Scherzer.
Scherzer had gone 9-11 with a 4.12 ERA, 1.34 WHIP and 174 strikeouts in 170.1 innings in his first full season in the majors in 2009, and he steadily developed into an ace after joining the Tigers, winning 2013 AL Cy Young honors.
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8. Gary Carter to the New York Mets
4 of 11
Date: Dec. 10, 1984
Transaction: Mets acquire C Gary Carter from the Expos for OF Hubie Brooks, RHP Floyd Youmans, C Mike Fitzgerald, OF Herb Winningham
After 11 seasons, seven All-Star selections, 215 home runs and 55.7 WAR as a member of the Expos, catcher Gary Carter was traded to the Mets ahead of his age-31 campaign.
Still a legitimate star, Carter slugged a career-high 32 home runs in his first season with the Mets, then helped lead the team to a World Series title in 1986 as the veteran leader on a young club headlined by Dwight Gooden and Darryl Strawberry.
He went 8-for-29 with two doubles, two home runs and nine RBI against the Red Sox in the 1986 World Series, and was a four-time All-Star and two-time Silver Slugger winner over his five seasons with the Mets.
7. Chris Sale to the Boston Red Sox
5 of 11
Date: Dec. 6, 2016
Transaction: Red Sox acquire LHP Chris Sale from White Sox for 3B Yoán Moncada, RHP Michael Kopech, OF Luis Alexander Basabe, RHP Victor Diaz
At the time of this trade, Yoán Moncada was No. 2 on the Baseball America Top 100 prospect list, while Michael Kopech checked in at No. 32, making it one of the most significant prospect hauls ever acquired.
However, it was the Red Sox who undoubtedly won this deal with the benefit of hindsight, as Moncada failed to live up to superstar expectations and Kopech never carved out a spot in the rotation.
Meanwhile, Sale put up elite numbers in 2017 (17-8, 2.90 ERA, 308 K, 214.1 IP) and 2018 (12-4, 2.11 ERA, 237 K, 158.0 IP), and he was the ace of the staff for the 2018 World Series champions.
6. Adam Wainwright to the St. Louis Cardinals
6 of 11
Date: Dec. 13, 2003
Transaction: Cardinals acquire RHP Adam Wainwright, RHP Jason Marquis, LHP Ray King from Braves for OF J.D. Drew, OF Eli Marrero
Outfielder J.D. Drew was one of the top players on the trade market during the 2003-04 offseason, as the former top prospect had developed into a solid contributor with 17.2 WAR over five seasons in the St. Louis outfield.
He ended up turning in the best season of his career as a one-year rental in Atlanta, hitting .305/.436/.569 with 31 home runs, 93 RBI and 8.3 WAR before joining the Dodgers in free agency that winter, but the Braves failed to advance beyond the NLDS.
The cost to acquire that one fantastic season of production proved to be extremely steep, as Adam Wainwright would develop into one of the best pitchers of his era over 18 seasons in St. Louis. To his credit, Jason Marquis was also a rock solid member of the Cardinals rotation, making 97 starts and chewing up 602.2 innings in three seasons.
5. Frank Robinson to the Baltimore Orioles
7 of 11
Date: Dec. 9, 1965
Transaction: Orioles acquire OF Frank Robinson from the Reds for RHP Milt Pappas, RHP Jack Baldschun and OF Dick Simpson
As the story goes, Reds owner Bill DeWitt referred to Frank Robinson as "an old 30" in an effort to justify to the fanbase the decision to trade the future Hall of Famer to the Orioles during the 1965 winter meetings.
The deal brought back a solid rotation piece in Milt Pappas, but that was not enough to save it from being widely regarded as one of the worst trades in baseball history.
Robinson went on to play 11 more seasons, six of which were in Baltimore where he hit .300/.401/.543 with 179 home runs and 32.4 WAR. He won the AL Triple Crown and both AL MVP and World Series MVP in 1966, and was instrumental in delivering another title in 1970.
4. Roger Maris to the New York Yankees
8 of 11
Date: Dec. 11, 1959
Transaction: Yankees acquire OF Roger Maris, SS Joe DeMaestri, 1B Kent Hadley from the Athletics for OF Hank Bauer, RHP Don Larsen, 1B Norm Siebern, 1B Marv Thorneberry
Over three big league seasons, Roger Maris had done little to hint at his future stardom, hitting .273/.359/.464 with 16 home runs and 72 RBI in his final season with the Athletics before he was traded in a seven-player deal at the 1959 winter meetings.
The trade sent aging star Hank Bauer and World Series hero Don Larsen the other way, but a year later there was little doubt the Yankees had pulled off a massive heist.
Maris had a 39-homer, 112-RBI season in his Yankees debut while leading the AL with 7.5 WAR and taking home AL MVP honors, and the following season he turned in his record-setting 61-homer performance to capture MVP for the second year in a row. His peak was relatively short, but as memorable as any in baseball history.
3. Roberto Alomar, Joe Carter to the Toronto Blue Jays
9 of 11
Date: Dec. 5, 1990
Transaction: Blue Jays acquire 2B Roberto Alomar, OF Joe Carter from the Padres for 1B Fred McGriff, SS Tony Fernandez
With a young John Olerud waiting in the wings to take over at first base, the Blue Jays made the bold decision to trade established star Fred McGriff following a 1990 season where they went 86-76 and finished second in the AL East standings.
The deal ended up being the move that pushed them over the top, as Joe Carter effectively replaced McGriff's run production in the middle of the lineup, while a 23-year-old Roberto Alomar blossomed into a star in Toronto.
After a trip to the ALCS in 1991, the Blue Jays won back-to-back World Series titles in 1992 and 1993, with Alomar as the team's WAR leader during the '92 season and Carter delivering one of the most memorable home runs in MLB history to end the '93 series.
2. Miguel Cabrera to the Detroit Tigers
10 of 11
Date: Dec. 4, 2007
Transaction: Tigers acquire 3B Miguel Cabrera, LHP Dontrelle Williams from the Marlins for LHP Andrew Miller, OF Cameron Maybin, RHP Burke Badenhop, C Mike Rabelo, RHP Frankie De La Cruz, RHP Dallas Trahern
After debuting as a 20-year-old for a Marlins team that went on to win the World Series in 2003, Miguel Cabrera hit .318/.396/.551 while averaging 31 home runs and 115 RBI over the next four seasons to establish himself as one of the game's brightest young stars.
However, that was not enough to keep the penny-pinching Marlins from trading him away, alongside Dontrelle Willis in a deal that brought back a haul of prospect talent that never came close to equalling one of the greatest right-handed hitters the game has ever seen.
Cameron Maybin and Andrew Miller were two of the top prospects in all of baseball at the time of the trade, and both went on to productive big league careers, but they provided a combined 0.1 WAR during their time with the Marlins.
1. Joe Morgan to the Cincinnati Reds
11 of 11
Date: Nov. 29, 1971
Transaction: Reds acquire 2B Joe Morgan, OF César Gerónimo, RHP Jack Billingham, 3B Denis Menke, OF Ed Armbrister from the Astros for 1B Lee May, 2B Tommy Helms, OF Jimmy Stewart
It's not unreasonable to say there is no "Big Red Machine" without this trade.
Joe Morgan already had nine big league seasons under his belt in Houston before he was traded to the Reds, with a pair of All-Star selections and 27.0 WAR to his credit, but he immediately went from solid everyday player to one of the best players in the sport after coming to Cincinnati.
His first five seasons deserve to be fully appreciated:
1972: .292/.417/.435, 43 XBH, 73 RBI, 122 R, 58 SB, 9.3 WAR
1973: .290/.406/.493, 63 XBH, 82 RBI, 116 R, 67 SB, 9.3 WAR
1974: .293/.427/.494, 56 XBH, 67 RBI, 107 R, 58 SB, 8.6 WAR
1975: .327/.466/.508, 50 XBH, 94 RBI, 107 R, 67 SB, 11.0 WAR
1976: .320/.444/.576, 62 XBH, 111 RBI, 113 R, 60 SB, 9.6 WAR
The Reds won three NL pennants and two World Series titles during that stretch, while Morgan was a five-time All-Star, four-time Gold Glove winner and two-time NL MVP.
Not to be completely overlooked, César Gerónimo also won four Gold Gloves in center field and tallied 13.2 WAR over nine seasons with the Reds, while Jack Billingham won 87 games in six seasons and finished top 10 in NL Cy Young balloting twice.
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