3 Former Cubs Theo Epstein Could Bring to Boston

With Theo Epstein re-joining Fenway Sports Group as a part owner, don't be surprised if he lures these three former Chicago Cubs to the Boston Red Sox.

Theo Epstein could potentially lure these three former Cubs to the Red Sox after making his Boston return. / Winslow Townson-USA TODAY Sports

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2. Rich Hill, SP

The Red Sox are looking to improve the starting rotation this offseason and I wouldn't be surprised if Rich Hill was signed as a depth arm.

Hill is someone that Epstein, Red Sox fans, and Cubs fans are all familiar with. The 43-year-old began his 19-year career with Chicago in 2005 and enjoyed a brief stop in Baltimore before joining the Epstein-led Red Sox in 2009. Hill didn't see much playing time in his first three seasons with Boston, making 40 appearances without a start before leaving town in 2013.

Hill has had two more stints in Beantown since then (most recently in 2022) and it's clear that he plays some of his best baseball in a Red Sox uniform. He's played a total of 70 games (30 starts) across five seasons with the franchise, going 12-8 with a 3.31 ERA while averaging 8.8 strikeouts per nine innings.

The Boston native has recently declared that he might wait until halfway through the 2024 schedule to sign a contract. Although he wasn't particularly impressive in 2023 (8-14, 5.41 ERA in 32 games/27 starts), I'm not opposed to a well-rested Hill joining the Red Sox as someone who can play at the end of the rotation or be inserted into the lineup when injuries arise.

After all, what better place to end his career than in his hometown?

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