Red Sox Could Acquire Cubs Lefty All-Star In Offseason Blockbuster, Insider Says

Pitching will be a hot commodity this winter...

Apr 3, 2019; Atlanta, GA, USA; Detailed view of Chicago Cubs hats and gloves in the dugout against the Atlanta Braves in the fifth inning at SunTrust Park. Mandatory Credit: Brett Davis-Imagn Images / Brett Davis-Imagn Images

Until the Boston Red Sox add at least one starting pitcher, not much else will matter to their chances of playoff contention.

The Red Sox rotation wasn't bad by any means in 2024--it overperformed expectations given all the question marks about the pitchers included at the start of the season. But the depth wore thin and most of the starters tired during the dog days of summer, which led to a losing stretch that ultimately tanked Boston's season.

Heading into 2025, the Red Sox are perhaps just one arm away from securing a much-needed return to the playoffs. And perhaps Chief Baseball Officer Craig Breslow can look to a familiar place to find the starting pitching help he desires.

Breslow came from the Chicago Cubs at the end of the 2023 season, and it just so happened that the Cubs had an All-Star pitcher that year who could be available if the price is right. Chris Cotillo of MassLive recently named lefty star Justin Steele as a possible Red Sox offseason trade target.

"John Henry’s curious recent spending habits and the massive surplus of young position players in the organization would seem to form a perfect storm in which Breslow is set up nicely to try to make a trade like the 2017 deal that brought Chris Sale to Boston for a package headlined by Yoan Moncada and Michael Kopech," Cotillo said. "What about old friend Justin Steele with the Cubs?"

Steele, 28, looks to be a borderline ace in this league after his performance the last three years combined. He has a 3.10 ERA/3.14 FIP with 437 strikeouts in 427 innings in that time frame, which comprises 78 games started.

Bringing Steele to Boston would solve a lot of issues. He'd finally give them a lefty in the starting rotation, and a darned good one at that. He's also proven he can consistently pitch six or more innings, which was a real struggle for the Red Sox during the summer.

It's only speculation at this point, but Steele really could be the perfect fit for the Red Sox this winter. Whether or not the Cubs will be willing to trade him, though, is up in the air.

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