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This year, the Winter Meetings will take place in Orlando, Florida, from December 7-10. These meetings are renowned for major signings and trades, with all 30 MLB teams sending representatives alongside players, agents, and media. Notably, high-profile trades and signings — such as Juan Soto being traded to the New York Yankees and then signing a $765 million contract with the New York Mets, Miguel Cabrera being traded to the Detroit Tigers, and Shohei Ohtani signing a massive $700 million contract with the Los Angeles Dodgers — have highlighted the undeniable significance of this period for player movement.
During last year's Winter Meetings, the Red Sox made the massive move in acquiring Garrett Crochet from the Chicago White Sox. Crochet lived up to the hype during the season, posting a 2.59 ERA, an 18-5 record, and a 255:46 strikeout-to-walk ratio over 205 1/3 innings. He's in prime form to carry this starting rotation for at least the next five years throughout the duration of the $170 million contract the lefty signed after landing in Boston last December.
The Red Sox's significant needs for the upcoming season are on the pitching staff, which they addressed with short-term band-aids by acquiring Sonny Gray from the St. Louis Cardinals on November 25 and Johan Oviedo from the Pittsburgh Pirates on December 4.
The pitching staff will still be the primary focus during the Winter Meetings, as will the the decision to re-sign Alex Bregman or let him go. While we wait for the news to drop, let's take a look at other notable acquisitions and failures the Red Sox have made during this time period.
During the 2016 Winter Meetings, the Red Sox went after another White Sox player, acquiring Chris Sale in exchange for Yoan Moncada, Michael Kopech, Luis Alexander Basabe, and Victor Diaz. Sale was phenomenal in his first two seasons in Boston, posting 2.90 and 2.11 ERAs, respectively, combining for a 545:77 strikeout-to-walk ratio, and a 29-12 record over 372 1/3 innings. Sale would earn his only two All-Star appearances as a Red Sox in those two campaigns seasons. During the 2023 offseason, he'd get traded to the Atlanta Braves, where he won the NL Comeback Player of the Year and Cy Young Award that following season.
Not to be topped, in 2000, the Red Sox were the big talk of the Winter Meetings after agreeing to an eight-year $160 million contract with Manny Ramirez. He had a stellar seven-and-a-half years in Boston, hitting 274 home runs before being traded to the Los Angeles Dodgers during the 2008 trade deadline.
The 1987 Winter Meetings led to the Red Sox answering their closer question that offseason by acquiring Lee Smith from the Chicago Cubs for Calvin Schiraldi and Al Nipper. Smith spent two and a half seasons with the Red Sox, successfully converting 58 save opportunities.
The Red Sox have also been on the wrong side of Winter Meetings acquisitions. In 2004, Boston tried to re-sign Pedro Martinez; however, they were outbid by the Mets. The Red Sox didn't want to guarantee a fourth season, which led to Martinez's decision not to not re-sign. They were outbid again in 2014 for a former player, but this time it was Jon Lester signing with the Chicago Cubs. History repeated itself in 2022, when the Red Sox sought to re-sign Xander Bogaerts but were outbid by the San Diego Padres.
This offseason's Winter Meetings will revolve around the possibility of re-signing Alex Bregman. Fans will hope history doesn't repeat itself and that the team doesn't lose out on bringing back a key player. Other than Bregman, the focus will continue to be on reshaping the pitching staff for the 2026 season.
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