Cubs Could Trade For Former Red Sox Right-Hander To Prepare For Playoffs

An ex-Red Sox hurler might end up in Chicago by July

Apr 26, 2015; Cincinnati, OH, USA; A Chicago Cubs hat and glove sits in the dugout during a game with the Cincinnati Reds at Great American Ball Park. Mandatory Credit: David Kohl-Imagn Images | David Kohl-Imagn Images

The Chicago Cubs’s late-inning bullpen arsenal might soon feature two former Boston Red Sox relievers.

Technically, Chicago’s 36-year-old closer Ryan Pressly never played for the Red Sox’s big-league team, but he was drafted by Boston in 2007 and spent half a decade in its minor league system.

Pressly, a two-time All-Star and 2022 World Series champ with the Houston Astros, has been solid for the Cubs this season, accruing a 2-1 record, 2.08 ERA, and four saves in 13 appearances for a hot 21-13 Chicago club looking poised to seize the National League Central crown.

Given Pressly’s age, the Cubs would be wise to add another closer-type to their ‘pen before the deadline, if only to serve as a reliable setup man for Pressly and/or as the team’s backup closer.

And according to new comments from MLB Networks’ Greg Amsinger made this week on MLB Tonight, another ex-Red Sox closer promises to be available on the trade market this summer.

“Kenley Jansen looks terrific,” Amsinger said on Wednesday night.

“The (Los Angeles) Angels just don't look good right now. Last week and a half, they've been terrible. Kenley looks great. And if this future Hall of Famer wants to be in a winning environment, the velocity, (and) the spin is all a plus. Kenley will be on the move.”

Jansen suffered his first bad outing of 2025 on Friday versus the Detroit Tigers, allowing six earned runs in 2/3 innings and swallowing the loss.

Before that, Jansen hadn’t allowed a run in six appearances and was looking like one of Major League Baseball’s premier trade chips.

Friday will likely prove to be an outlier for the 37-year-old Jansen. Contending teams like the Cubs pursuing postseason glory in 2025 have reason to monitor Jansen and his expiring $10 deal.

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