Red Sox's Top 5 Winter Meetings deals

For the Red Sox, some of the most memorable transactions in team history took place amid the chaos of the Winter Meetings.

It was in that setting that Dan Duquette landed a star slugger in his prime who would end up producing countless highlights -- and moments of comic relief -- in an eight-season run in Boston.

It was also when Dave Dombrowski dealt two of his top prospects for an overpowering ace in Chris Sale. Red Sox chief baseball officer Craig Breslow went to that same playbook to land Garrett Crochet eight years later. Theo Epstein and Ben Cherington both used the Winter Meetings as the opportunity to land an elite closer who would go on to throw the final pitch of a World Series.

Here are the top five Winter Meetings moves in Red Sox history.

1. Dec. 19, 2000: Red Sox sign free-agent OF Manny Ramirez to eight-year, $160 million deal
After facing star slugger Manny Ramirez in the American League Division Series three times in five seasons, the Red Sox knew what a fearsome offensive threat they were courting 20 years ago. Earlier in the offseason, the Sox lost out on their top target when ace Mike Mussina went to the Yankees. But Duquette quickly shifted to Plan B and acquired one of the most impactful hitters in Red Sox history.

“It was important for us to get a player like that, and for us to have really good, identifiable players from a competitive basis," Duquette said. "We thought that Manny would be a long-time fixture and fit in with the tradition of great Red Sox sluggers in left field."

While Ramirez’s various quirks always drew the refrain, “Manny being Manny,” that shouldn’t overshadow his consistent excellence in his eight years with Boston. Ramirez was a central member of the 2004 “Idiots” squad that ended the 86-year championship drought and also came up big in the title run of ’07. Ramirez played 1,083 games for the Red Sox, slashing .312/.411/.588 to go with 274 homers and 868 RBIs.

2. Dec. 6, 2016: Red Sox acquire LHP Chris Sale from White Sox for 2B Yoan Moncada, RHP Michael Kopech, OF Luis Alexander Basabe, RHP Victor Diaz
Dombrowski made the biggest blockbuster trade of his eventful four-year run with the Red Sox when he acquired an ace in his prime, Chris Sale. It didn’t come cheaply, as Boston served up two of its most highly touted prospects in Yoán Moncada and Michael Kopech. The deal swiftly paid dividends as Sale put together back-to-back excellent seasons in 2017-18 as the Red Sox extended their run of consecutive AL East titles to three.

In 2017, Sale recorded 308 punchouts, second to Pedro Martinez’s 313 strikeouts in ’99 for the best in team history. Though Sale battled some shoulder issues in ’18, he was superb in his 27 starts (2.11 ERA, 0.86 WHIP). And when the Red Sox clinched their fourth World Series title in 15 seasons that year, it was Sale who threw the final pitch, buckling Manny Machado with a wicked slider.

3. Dec. 11, 2024: Red Sox acquire LHP Garrett Crochet from White Sox for OF Braden Montgomery, C Kyle Teel, RHP Wikelmen González and INF Chase Meidroth
Just like eight years earlier, the Red Sox were trying to vault back to World Series contention while the White Sox were in a rebuild. So Boston was able to land the modern-day Sale for four prospects, putting the Red Sox back on the path to October after missing the playoffs three straight years. The deal became even more impactful shortly after the ‘25 season started when the Sox agreed with Crochet on a six-year, $170-million contract extension.

4. Dec. 13, 2003: Red Sox sign RHP Keith Foulke to a three-year contract with a vested option for fourth year
At Thanksgiving, the Red Sox made a move that sent a happy jolt throughout New England, landing Curt Schilling in a trade with the D-backs. But they still needed a premier closer to get over the sting of 2003, and Epstein got his man in Keith Foulke.

In large part due to Foulke’s performance in the regular season and postseason, Boston won that long-awaited 2004 World Series. While Schilling and David Ortiz and Dave Roberts seem to get the most credit for that amazing October, Foulke was probably the team’s MVP throughout the month of October, as he notched a 0.64 ERA while pitching in 11 of Boston’s 14 postseason games. When the Sox trailed the Yankees, 3-0, in the AL Championship Series, Foulke threw 100 pitches over the next three games to set up Game 7.

5. Dec. 18, 2012: Red Sox sign RHP Koji Uehara to one-year, $4.25 million deal
When the Red Sox first secured the services of Koji Uehara, it was hardly a blip on the radar. At the time, Joel Hanrahan was supposed to be the closer, and if that failed, Andrew Bailey was Plan B. But both of those pitchers were ineffective and injured. By June, Uehara took over the ninth inning and responded with one of the best seasons by a reliever in franchise history. In 73 appearances, Uehara had a 1.09 ERA and a 0.57 WHIP. In 74 1/3 innings, he tallied 101 strikeouts and just nine walks.

In Boston’s 2013 title run, Uehara was every bit as effective as Foulke was in ’04, converting all seven of his save opportunities with a 0.66 ERA. Uehara clinched all three playoff rounds with a game-ending strikeout. Remarkably, he didn’t walk a batter during the playoffs. Uehara had three more solid seasons with the Red Sox and was a fan favorite.