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.
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:
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: five-tool infielder Yoan Moncada (No. 1), hard-throwing right-hander Michael Kopech (No. 5), switch-hitting outfielder Luis Basabe (No. 8) and righty Victor Diaz (No. 28). 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.
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, who 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. Early returns on the deal heavily favor the Braves, as Miller posted a 6.15 ERA in his first year in Arizona as the D-backs lost 93 games, while Swanson hit .302 in his brief debut while looking like the cornerstone of the Braves’ rebuild.
Video: Bowman on Braves dealing for Swanson, Inciarte, Blair
2009: Three-team stunner
The D-backs, Tigers and Yankees pulled off the biggest three-team trade in Winter Meetings history in 2009 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 would hit 115 homers in four seasons in the Bronx and earn a fourth-place AL MVP Award finish in ’11.
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.
Video: Gilbert looks back on the Scherzer trade from 2009
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 one of the biggest deals of the past decade, 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 he’s signed with the Tigers through the 2023 season.
Video: WS2012 Gm3: Miggy receives trophy for Triple Crown
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.
Video: Must C Classic: Carter’s walk-off HR wins 1993 WS
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 would swipe 326 bags and record 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 would eventually send Rickey back to Oakland in 1989, where he would break the all-time stolen-base record two years later.
Video: Rickey Henderson takes his talent to the Bronx
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.
Video: Carter’s first home opener at Shea ends with homer
1980: Herzog rebuilds the Redbirds
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 then 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.
Video: MLB Productions recalls the 1982 World Series
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 would then go 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.
Video: [email protected]: Frank Robinson hits 500th home run
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.
Video: [email protected]: Maris hits his 60th home run of 1961
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.
AJ Cassavell is a reporter for MLB.com. Follow him on Twitter @ajcassavell.