The Cubs' Biggest Winter Meetings Acquisitions Of Years Past

[Bryan Jaeger]

Image courtesy of © Ray Carlin-Imagn Images / © Mike Dinovo-Imagn Images

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 to mingle and negotiate with players, agents, and media. High-profile trades—such as Garrett Crochet to the Boston Red Sox, Juan Soto to the New York Yankees, Chris Sale to the Red Sox, and Miguel Cabrera to the Detroit Tigers—dominate the headlines. It's as intense a four-day span as there will be all offseason.

The Cubs themselves capitalized on this setting last offseason, acquiring Kyle Tucker from the Houston Astros and agreeing to sign free-agent catcher Carson Kelly during the Meetings. Their impact was evident, but with Tucker now a free agent, the front office shifts its focus to acquiring a depth bat, a front-end starter, and bullpen help.

As speculation builds about what moves the Cubs might make this offseason, let's revisit the most impactful Winter Meetings acquisitions in the franchise's history.

Jon Lester's signing stands out as perhaps the most impactful. At a time when the franchise sought to move out of a rebuilding phase, Lester's arrival—via a six-year, $155 million contract after the 2014 season—signaled the Cubs' intent to contend.

During Lester's tenure, the Cubs made five postseason trips and won the 2016 World Series. During that season, he had a 19-5 record, 2.44 ERA, and a 197:52 strikeout-to-walk ratio. The lefty would finish the season as the runner-up to the Washington Nationals' Max Scherzer in the National League Cy Young voting. He threw more than 140 innings in every season except one (the 2020 Covid-shortened season).

After his contract expired, the Cubs declined his $25 million mutual option for the 2021 season, making Lester a free agent. He would sign with the Nationals, get traded to the St. Louis Cardinals at the trade deadline, and then hang his cleats up after the 2021 season.

During the 2015 Winter Meetings, the Cubs bolstered their offense by adding Ben Zobrist, fresh off his World Series win with the Kansas City Royals. The utility player signed a four-year, $56 million contract with the Cubs. To make room for Zobrist, the Cubs made a separate trade, sending Starlin Castro to the New York Yankees. During that season, Zobrist hit .272/.386/.446 with 18 home runs, 94 runs, and 76 RBIs over 632 plate appearances, earning his only All-Star appearance as a Cub.

In the 2016 World Series, Zobrist went 10-for-28 with five runs and two RBIs, and it was his go-ahead hit at the top of the 10th inning of Game 7 that put the Cubs up 8-7. They'd hold on in the bottom half, breaking their 108-year title drought, with Zobrist earning the MVP honors. His four seasons with the Cubs marked the end of his career.

A notable Winter Meetings trade came in 1980, when the Cubs traded their four-time All-Star closer, Bruce Sutter, to the St. Louis Cardinals. Sutter was perfect, saving 133 games during the 1976-1980 seasons as a member of the Cubs, without blowing a save opportunity. In 1979, he earned the NL Cy Young Award, posting a 2.22 ERA, 110:32 strikeout-to-walk ratio, and converted all 37 save opportunities over 101.1 innings.

A contract dispute led to the trade, but in return for Sutter, the Cubs received Leon Durham, Ken Reitz, and Ty Waller from the St. Louis Cardinals. This trade benefited both teams, as Sutter continued his dominant pitching in three of his first four years in St. Louis. For the Cubs, Durham played eight seasons, hitting 138 home runs and earning two All-Star appearances. Reitz and Waller weren't major contributors in their short-lived careers in Chicago.

This offseason's Winter Meetings may be busy for the Cubs. Shota Imanaga surprisingly accepted his one-year, $22.025 million qualifying offer over becoming a free agent. Still, the Cubs could use another front-line starting pitcher, with Justin Steele likely to miss at least the first half of the season after undergoing Tommy John surgery early into last season. The bullpen needs an overhaul, and the offense could use a depth bat, especially if Matt Shaw continues to struggle at the plate or if Owen Caissie isn't ready for the big leagues.

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