Red Sox All-Star Predicted To Ditch Boston For Cubs In Free Agency

Is this a good outcome for the Red Sox or a bad one?

Aug 12, 2023; Toronto, Ontario, CAN; A Chicago Cubs helmet rests on the dugout during a MLB game against the Toronto Blue Jays at Rogers Centre. Mandatory Credit: Kevin Sousa-Imagn Images | Kevin Sousa-Imagn Images

As free agency looms, few players around Major League Baseball have more complicated situations than Lucas Giolito.

Giolito saved the Boston Red Sox this season, pitching to a 10-4 record with a 3.41 ERA en route to the team's first playoff appearance since 2021. But he hurt his elbow at the very end of the regular season and wasn't able to pitch in the playoffs.

On Monday, the Red Sox declined Giolito's $19 million mutual option for next season, but the real decision is forthcoming, as he's eligible for a one-year, $22.025 million qualifying offer. That decision is due by Thursday, and if he declines the offer, the Red Sox would get a compensation pick in next July's draft.

Will Giolito walk in free agency?

Aug 15, 2025; Boston, Massachusetts, USA; Boston Red Sox starting pitcher Lucas Giolito (54) pitches against the Miami Marlins during the first inning at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images | Eric Canha-Imagn Images

There's still a lot to sift through, but at the end of the offseason, the important question is whether Giolito is pitching for the Red Sox or for some other team.

On Monday, Chris Cotillo of MassLive predicted that the former American League All-Star would take his talents to the Chicago Cubs, who needed starting pitching even before news of Shota Imanaga's impending free agency broke on Tuesday.

"There’s a real shot Giolito will get the qualifying offer from the Red Sox and accept it," wrote Cotillo. "But as a former top-ranking union member, he knows well the risk he’s taking by accepting a one-year deal, especially with the backdrop of his late-season elbow issues.

"The Cubs will have money to spend, especially if Kyle Tucker signs elsewhere, and Giolito is obviously familiar with Chicago after spending seven years pitching for the White Sox. The Red Sox would be thrilled to get a compensation pick here."

Giolito's under-the-hood numbers suggested that he got fairly lucky this season, and as important as the 145 innings he threw were, the Red Sox would ideally like more from someone in the No. 2 or 3 spot in their rotation.

But bidding farewell to a somewhat reliable arm is a risk in today's day and age. With the Cubs, Giolito would at least be out of the American League, but the Red Sox saw this year, with Nick Pivetta's success on the San Diego Padres, that addition by subtraction is far from guaranteed.

Giolito signing with the Cubs would be a positive outcome, but only if Boston replaced him on the payroll with a high-upside workhorse.

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