Each MLB Team’s Biggest Offseason Success of the Last 10 Years

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Chicago Cubs: Signed LHP Jon Lester (Dec. 15, 2014)
Trading for Dexter Fowler in Jan. 2015 was huge for the Cubs. Both in the regular season and postseason, he was indispensable in center field. But the acquisition of Jon Lester one month prior to that trade was even bigger in the quest to break the curse. It certainly wasn’t a cheap signing. That six-year, $155M deal was a big risk. In 2016, though, he almost won NL Cy Young and was phenomenal in the postseason, including his three-inning relief appearance in Game 7 of the World Series. The Cubs would have paid $300 million knowing he’d be that pivotal. Lester was also strong in 2015 and 2018.
Cincinnati Reds: Traded for RHP Luis Castillo (Jan. 19, 2017)
Castillo was traded four times before making his MLB debut, and it was Cincinnati who won that game of Prospect Hot Potato. In his five-plus seasons with the Reds, Castillo was worth 18.0 bWAR and the starting pitcher for one of the two postseason games this franchise has played in the past decade. And when the Reds decided to trade him away two summers ago, Castillo netted them Noelvi Marte, Levi Stoudt, Edwin Arroyo and Andrew Moore, which was quite the gift on his way out the door.
Milwaukee Brewers: Traded for OF Christian Yelich (Jan. 25, 2018)
During the 2014-15 offseason, the Miami Marlins signed Yelich to a seven-year extension for a total of just under $50M. But rather than keep him for the duration of the deal, they traded him to Milwaukee less than three years later for Lewis Brinson, Isan Diaz, Monte Harrison and Jordan Yamamoto—a quartet with a combined career bWAR of negative-6.8. Meanwhile, Yelich won NL MVP in his first season with the Brewers and narrowly missed winning it again in his second season.
Pittsburgh Pirates: Traded for OF Bryan Reynolds (Jan. 15, 2018)
One year away from reaching free agency for the first time in his career, the San Francisco Giants decided they couldn’t wait to get their hands on Andrew McCutchen, giving the Pirates Bryan Reynolds (and Kyle Crick) for Cutch’s expiring contract. It did not age well for the G-Men, who were sitting at .500 at the end of August when they traded him to the Yankees. But it worked out beautifully for the Pirates, with Reynolds playing well over the past five years and signed through at least 2030.
St. Louis Cardinals: Traded for 3B Nolan Arenado (Feb. 1, 2021)

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