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Most memorable moments in MLB Winter Meeting history
Gary Barber/Getty Images

Most memorable moments in MLB Winter Meeting history

Some of the biggest free agent signings and trades in MLB history have occurred during the Winter Meetings. Here's a look at some of the most memorable moves.

 

2017: Yankees get Giancarlo Stanton

2017: Yankees get Giancarlo Stanton
Steve Mitchell / USA Today Sports Images

It was clear the Marlins were headed for a firesale after an ownership group led by Derek Jeter purchased the team. Stanton had plenty of leverage with a no-trade clause, backing the Marlins into a corner until they shipped him to the Yankees during the Winter Meetings.

 

2016: Red Sox land Chris Sale from White Sox

2016: Red Sox land Chris Sale from White Sox
Gary A. Vasquez / USA Today Sports Images

Red Sox GM Dave Dombrowski had a reputation for making big deals, and the acquisition of Sale from the White Sox was one of his biggest. The deal still came at a heavy cost for Boston, trading four prospects, including elite prospects Yoan Moncada and Michael Kopech. The move paid has paid off big time for the Red Sox over the last two years, as they won the World Series in 2018.

 

2015: Arizona gives up a boatload for Shelby Miller

2015: Arizona gives up a boatload for Shelby Miller
Jennifer Stewart / USA Today Sports Images

GM Dave Stewart became a the focus of much ridicule when he traded 2015 first overall draft choice Dansby Swanson, Ender Inciarte, and Aaron Blair to Atlanta for Miller and Gabe Speier. Miller had played for Diamondbacks Chief Baseball Officer Tony La Russa in St. Louis, but the move turned out to be an even bigger disaster for Arizona than anticipated. Miller threw only 139 innings in three seasons for Arizona that included Tommy John surgery, posting a 6.35 ERA. Swanson and Inciarte have gone on to become solid contributors for the Braves.

 

2012: Royals get James Shields and Wade Davis

2012: Royals get James Shields and Wade Davis
Noah K. Murray / USA Today Sports Images

KC GM Dayton Moore faced heavy criticism when he traded top prospects Wil Myers, Mike Montgomery, and Jake Odorizzi to Tampa Bay for James Shields and Wade Davis. The trade eventually vindicated Moore, as the Royals reached the 2014 World Series with the duo, and won it all in 2015 after Shields departed. Myers, Montgomery, and Odorizzi have also gone on to become quality major league players.

 

2011: Albert Pujols signs with the Angels

2011: Albert Pujols signs with the Angels
Rick Scuteri / USA Today Sports Images

The wild-spending Marlins were rumored to be in on Pujols, but it was a surprise team that emerged instead. The Angels signed Pujols to a mammoth 10-year, $210 million contract going into his age 32 season. Pujols immediately declined upon leaving St. Louis and has continued to see his production slide in recent seasons.

 

2011: Marlins go on a spending spree

2011: Marlins go on a spending spree
Sarah Crabill / Getty Images

Miami ownership decided to go all-in during the 2011 Winter Meetings, signing Heath Bell, Mark Buehrle, and Jose Reyes to lucrative contracts for a combined $191 million. Even Albert Pujols was rumors to be going to Miami before signing with the Angels. The trio didn't stick around Miami for long, as all three were traded the following offseason.

 

2010: Phillies bring back Cliff Lee

2010: Phillies bring back Cliff Lee
Brian Garfinkel / Getty Images

Lee spent about two months with the Phillies in 2009 before the team traded him to Seattle, but that wasn't the last they would see of him. Philadelphia brought back the lefty on a five-year, $120 million contract during the 2010 Winter Meetings. The Phillies had a history starting rotation in 2011, with three of their starters, including Lee, finishing in the top five in the NL Cy Young vote.

 

2010: Jayson Werth moves to Washington

2010: Jayson Werth moves to Washington
Mitchell Layton / Getty Images

The Nationals won only 69 games in 2010, so it came as a shock to many when they signed Werth to a seven-year, $126 million contract during the Winter Meetings. The signing was considered a huge overpay at the time, but the team made the playoffs in Werth's second year with the team.

 

2010: Red Sox give up big prospect package for Adrian Gonzalez

2010: Red Sox give up big prospect package for Adrian Gonzalez
Elsa / Getty Images

Gonzalez had become a star in San Diego, making three consecutive All-Star appearances before he was traded during the Winter Meetings in 2010 to Boston for a package that included Rey Fuentes, Casey Kelly, and Anthony Rizzo. Gonzalez had a very good 2011 season for a 90-win Red Sox team, but was traded to the Dodgers during 2012.

 

2009: Yankees, Diamondbacks, Tigers agree to blockbuster 3-way deal

2009: Yankees, Diamondbacks, Tigers agree to blockbuster 3-way deal
Leon Halip / Getty Images

Potential blockbuster trades like the one the Yankees, Diamondbacks, and Tigers took part in during the 2009 Winter Meetings are what make the event so exciting. The three-way deal included seven players, with the Tigers receiving Phil Coke, Austin Jackson, Daniel Schlereth, and Max Scherzer, the Yankees receiving Curtis Granderson, and the Diamondbacks receiving Edwin Jackson and Ian Kennedy. Scherzer stands out in the deal, as he developed into a Cy Young winner for Detroit.

 

2008: Mariners, Mets, Indians complete 12-player trade

2008: Mariners, Mets, Indians complete 12-player trade
Jim McIsaac / Getty Images

Trades don't get much bigger than the blockbuster completed by the Mariners, Mets, and Indians in 2008. The deal was headlined with New York's acquisition of J.J. Putz, also receiving Sean Green and Jeremy Reed, giving up seven players: Aaron Heilman, Joe Smith, Mike Carp, Ezequiel Carrera, Endy Chavez, Maikel Cleto, and Jason Vargas. Cleveland received Luis Valbuena and Smith, sending Franklin Gutierrez to Seattle.

 

2008: CC comes to the Big Apple

2008: CC comes to the Big Apple
Nick Laham / Getty Images

CC Sabathia made himself a lot of money with a great playoff showing for the Brewers in 2008, signing a seven-year, $161 million contract with the Yankees during the Winter Meetings and also added A.J. Burnett. He proceeded to finish in the top four in AL Cy Young voting during his first three years with New York.

 

2007: Tigers get Miggy and Dontrelle

2007: Tigers get Miggy and Dontrelle
Mark Cunningham / Getty Images

The Marlins had an all-too-familiar firesale after the 2007 season, trading their two most recognizable players. They traded stars Miguel Cabrera and Dontrelle Willis to the Tigers for Dallas Trahern, Burke Badenhop, Frankie De La Cruz, Cameron Maybin, Andrew Miller, and Mike Rabelo. Willis would struggle after leaving Florida, but Cabrera has won two MVPs and five Silver Sluggers with Detroit.

 

2006: Reds purchase Josh Hamilton after Rule 5 draft

2006: Reds purchase Josh Hamilton after Rule 5 draft
Stephen Dunn / Getty Images

Drafted first overall by the Devil Rays in the 1999 amateur draft, Hamilton had well-publicized issues with drugs off the field. Seven years later, Tampa Bay left him off their 40-man roster, making him eligible for the Rule 5 draft. Hamilton was selected by the Cubs before getting traded to Cincinnati. Hamilton remained with the Reds for the entire 2007 season and had a good rookie year, but was traded to Texas for Edinson Volquez in the offseason.

 

2005: Nats get Alfonso Soriano from Texas

2005: Nats get Alfonso Soriano from Texas
Jim McIsaac / Getty Images

Coming off a 30/30 season in Texas, Soriano was traded during the Winter Meetings to the Nationals for Brad Wilkerson, Terrmel Sledge, and Armando Galarraga. Soriano spent only one season with the Rangers but had arguably the best year, hitting .277-46-95 with 41 stolen bases.

 

2003: Yankees get Kevin Brown from LA

2003: Yankees get Kevin Brown from LA
Tom Hauck / Getty Images

Kevin Brown was a big-ticket item at the Winter Meetings again, getting traded to the Yankees for Jeff Weaver, Yhency Brazoban, Brandon Weeden ( yes, that Brandon Weeden) and cash. Brown struggled in two seasons with the Yankees to finish off his career.

 

2003: Orioles land Miguel Tejada

2003: Orioles land Miguel Tejada
Kirby Lee / Getty Images

The 2002 AL MVP, Tejada was set for a big payday as he left Oakland following the 2003 season. Baltimore was the team to give it to him, signing Tejada to a six-year, $72 million contract. He had four good seasons in Baltimore but was traded to Houston before the contract expired.

 

2000: Alex Rodriguez announces record-breaking deal with Rangers

2000: Alex Rodriguez announces record-breaking deal with Rangers
Gary Barber / Getty Images

It was the contract heard around the world. A-Rod signed with the last place Rangers for 10-years, $252 million, the biggest contract in sports history at the time. While Rodriguez was terrific in three seasons with Texas, including the 2003 AL MVP, the Rangers were unable to put together a competitive team around him, and he was eventually traded to the Yankees in 2004.

 

2000: Red Sox get Manny

2000: Red Sox get Manny
J. Meric / Getty Images

Alex Rodriguez was the main headliner of the 2000 Winter Meetings, but Boston was also able to get their prize. Manny Ramirez signed an eight-year, $160 million contract with the Red Sox after leaving Cleveland. He made the All-Star Game in all eight of his seasons with Boston, also helping the team win two World Series.

 

2000: Mike Hampton moves to Denver for "the school system"

2000: Mike Hampton moves to Denver for "the school system"
Brian Bahr / Getty Images

The best pitcher available in the 2000 offseason, Hampton shocked the baseball world by signing with the Rockies during the Winter Meetings. The deal was for eight years, $121 million, but Hampton infamously said during his introductory press conference that he signed with Colorado for "the school system." The signing was a complete disaster for the Rockies, as Hampton was terrible after moving to Coors Field with a 5.75 ERA in 62 starts over the next two seasons before getting traded to Florida and then Atlanta.

 

1998: Kevin Brown breaks $100 million

1998: Kevin Brown breaks $100 million
Mike Nelson / AFP / Getty Images

Brown signed the first $100-plus million contract in baseball history during the 1998 Winter Meetings, agreeing to a seven-year, $105 million deal with the Dodgers. The contract had mixed reviews, but Brown was injured for a large portion of it before getting traded to the Yankees during the 2003 Winter Meetings.

 

1992: Barry Bonds comes home to San Francisco

1992: Barry Bonds comes home to San Francisco
Focus on Sport / Getty Images

Bonds spent the first seven seasons of his MLB career in Pittsburgh, but created a stir when he signed with the Giants for a record seven years, $43.75 million during the 1992 Winter Meetings. San Francisco was the same team his father, Bobby, and godfather, Willie Mays, played for during Bonds' childhood. Bonds spent the rest of his career with San Francisco, breaking the single-season and career home run records.

 

1990: Jays set stage for World Series by acquiring Joe Carter and Roberto Alomar

1990: Jays set stage for World Series by acquiring Joe Carter and Roberto Alomar
Rick Stewart / Getty Images

Toronto and San Diego pulled off a huge trade in 1990, as the Blue Jays moved Tony Fernandez and Fred McGriff to the Padres for Carter and Alomar. Carter and Alomar went on to have some of their best years north of the border, and helped the team win the 1993 World Series.

 

1988: Nolan Ryan becomes a Ranger

1988: Nolan Ryan becomes a Ranger
Otto Greule Jr. / Getty Images

The Rangers were busy during the 1988 Winter Meetings, but their biggest move was signing Ryan. Entering his age 42 season, Ryan was still very good in 1989 (16-10 with a 3.20 ERA and league-high 301 strikeouts and ended up pitching a total of five seasons for Texas.

 

1984: Gary Carter becomes a Met

1984: Gary Carter becomes a Met
MLB Photos / Major League Baseball / Getty Images

Carter spent most of his career behind the plate for the Expos, but was traded by Montreal to the Mets during the 1984 Winter Meetings for Hubie Brooks, Mike Fitzgerald, Herm Winningham, and Floyd Youmans. He went on to make four All-Star appearances in five years with New York and won the 1986 World Series.

 

1984: Yankees get Rickey

1984: Yankees get Rickey
Focus on Sport / Getty Images

The premier leadoff man in baseball, Henderson was traded from Oakland, along with Bert Bradley, to the Yankees for Tim Birtsas, Jay Howell, Stan Javier, Eric Plunk, and Jose Rijo. He spent four-plus years in New York before getting traded back to Oakland in 1989.

 

1980: Dave Winfield signs 10-year deal with Yankees

1980: Dave Winfield signs 10-year deal with Yankees
Bettmann / Getty Images

Winfield signed with the Yankees for 10-year, $23 million during the 1980 Winter Meetings, one of the most infamous contracts in baseball history. Yankees owner George Steinbrenner thought he was signing Winfield for only $16 million, but cost-of-living increases in the contract gave Winfield $7 million more. The discrepancy created a feud between Winfield and Steinbrenner and in 1990, Steinbrenner paid Howie Spira, an admitted gambler, $40,000 to dig up dirt on Winfield. "The Boss" was banned from running the Yankees, as a result.

Seth Trachtman

Seth Trachtman is a sportswriter, digital marketer, and fantasy sports expert based in St. Louis, Missouri. He’s a two-time winner of the Tout Wars Fantasy Baseball Expert’s League, and his work has appeared in hundreds of fantasy baseball and fantasy football newsstand and online publications

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Cubs Have Another Breakout Hitting Prospect Rising Fast In Farm System Thanks To Consistent Bat
MLB

Cubs Have Another Breakout Hitting Prospect Rising Fast In Farm System Thanks To Consistent Bat

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NFL

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NFL

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NBA

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