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Cubs In Talk To Inked Another $4.5 Million Deal Alongside 3 Time Baseball Star

Posted on April 16, 2025

The Chicago Cubs recently acquired Ryan Pressly, a star closer from the Houston Astros, in a trade that came together quickly.

Following this move, the Cubs could benefit from adding another left-handed reliever to work alongside Pressly in the late innings.

Michael Brakebill from FanSided recently suggested that the Cubs might sign free-agent reliever Andrew Chafin to help strengthen their bullpen. Chafin is expected to sign a contract worth around $4.5 million this winter, according to Spotrac.

Brakebill noted that the Cubs addressed one of their major needs by signing Caleb Thielbar, a left-handed reliever, but pointed out that Thielbar struggled against left-handed hitters in 2024, allowing 10 earned runs in 22.1 innings and posting a 4.03 ERA.

However, his 2.59 FIP against lefties offers some hope for improvement. Still, the Cubs could use a more reliable southpaw like Chafin.

Mark Cunningham/MLB Photos via Getty Images

Chafin, known as the “Sheriff,” had a solid stint with the Cubs in 2021, posting a 2.06 ERA. Though he primarily served as a setup man, his experience in that role could be valuable for the Cubs, with Pressly likely taking over closing duties.

At 34, Chafin posted a respectable ERA and a 116 ERA+, making him an ideal left-handed option for the Cubs’ bullpen. At around $4 million, Chafin wouldn’t be expected to be a superhero, but rather a dependable reliever to get key outs against left-handed hitters late in games, setting up Pressly for saves.

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