Inside The Red Sox

Ex-Red Sox Starter's Remarkable Comeback Story Continues During Cubs' NLDS Run

He even got a ring with the 2018 Sox...
Jackson Roberts|
Sep 13, 2025; Chicago, Illinois, USA; Chicago Cubs pitcher Drew Pomeranz (45) prepares to pitch against the Tampa Bay Rays during the sixth inning at Wrigley Field. Mandatory Credit: Patrick Gorski-Imagn Images
Sep 13, 2025; Chicago, Illinois, USA; Chicago Cubs pitcher Drew Pomeranz (45) prepares to pitch against the Tampa Bay Rays during the sixth inning at Wrigley Field. Mandatory Credit: Patrick Gorski-Imagn Images | Patrick Gorski-Imagn Images

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There are a select few former Boston Red Sox still making an impact on the postseason.

Boston was eliminated last Thursday by the New York Yankees, and entering play on Saturday, only five teams are still fighting for a World Series title. Obviously, Mookie Betts and Kiké Hernández are still alive with the Los Angeles Dodgers, but some lesser-known former Sox are playing key roles as well.

A night after little-known former Red Sox reliever Eduard Bazardo made a heroic extra-innings appearance for the Seattle Mariners, the Chicago Cubs will send Drew Pomeranz to the mound on Saturday, continuing a remarkable story.

Pomeranz to start Game 5 of NLDS

Drew Pomeranz
Sep 7, 2025; Chicago, Illinois, USA; Chicago Cubs pitcher Drew Pomeranz (45) throws the ball against the Washington Nationals during the first inning at Wrigley Field. Mandatory Credit: David Banks-Imagn Images | David Banks-Imagn Images

Pomeranz, the 36-year-old lefty, pitched for the Red Sox from 2016 to 2018, a tenure marked by serious peaks and valleys. He won 17 games in 2017, then struggled mightily in 2018, though he did get a World Series ring after missing out on the playoff roster.

But Pomeranz's career easily could have been over after the 2021 season, when he was an effective reliever for the San Diego Padres. He had two elbow surgeries and didn't appear in a Major League Baseball game for over three years.

But after not making the Seattle Mariners' roster out of spring training this year, Pomeranz was traded to the Cubs, and he went right back to being one of the best lefty relievers in baseball.

In 57 appearances, he put up a sparkling 2.17 ERA and 57 strikeouts in 49 2/3 innings. His lifetime 2.32 ERA as a reliever (in 201 appearances) is nothing short of remarkable.

Now, in the biggest game of the season, Pomeranz will be the first Cubs pitcher to take the ball against the Milwaukee Brewers, Chicago's biggest rival and the team with the best regular-season record in baseball this season.

It's storybook-type stuff, and although he doesn't have any more former Red Sox teammates still in Boston, one has to imagine there are plenty of Bostonians rooting for Pomeranz to keep the Cubs' season alive.

More MLB: Red Sox Lose 7-Year Veteran To Free Agency After Memorable Season

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Jackson Roberts
JACKSON ROBERTS

Jackson Roberts is a former Division III All-Region DH who now writes and talks about sports for a living. A Bay Area native and a graduate of Swarthmore College and the Newhouse School at Syracuse University, Jackson makes his home in North Jersey. He grew up rooting for the Red Sox, Patriots, and Warriors, and he recently added the Devils to his sports fandom mosaic. For all business/marketing inquiries regarding Boston Red Sox On SI, please reach out to Scott Neville: scott@wtfsports.org

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