Chicago Cubs Predicted to Sign Red Sox 18-Win Star Pitcher in Major Move

Toronto Blue Jays v Boston Red Sox
Getty
BOSTON, MA - JULY 25: Sonny Gray #54 of the Boston Red Sox pitches against the Toronto Blue Jays during the first inning at Fenway Park on July 25, 2026 in Boston, Massachusetts. (Photo By Winslow Townson/Getty Images)

The Chicago Cubs should be aggressive in free agency after a disappointing free agency.

It is no secret that the Cubs’ biggest objective this offseason should be to improve their pitching rotation. They need to add at least one high-impact starting pitcher if they hope to be a more significant threat next season.

Due to this, the Cubs are already being connected to a star pitcher from the Boston Red Sox.


Chicago Cubs Predicted to Sign Boston Red Sox Star Pitcher Sonny Gray

American League Wild Card: Boston Red Sox v New York Yankees - Game Two
GettyNEW YORK, NEW YORK – SEPTEMBER 30: Sonny Gray #54 of the Boston Red Sox reacts in the fourth inning against the New York Yankees in game two of the American League Wild Card Series at Yankee Stadium on September 30, 2026 in the Bronx borough of New York City. (Photo by Elsa/Getty Images)

In a recent article for Sports Illustrated, Justin Binkowski named the Cubs among the top landing spots for Red Sox star pitcher Sonny Gray this offseason.

“If Gray does become a free agent, he could be one of the top candidates to be Chicago’s ace next season,” Binkowski wrote. “Gray has experience pitching in the National League Central with the Cincinnati Reds and the St. Louis Cardinals. A return to that division could be an option for the veteran hurler if the Cubs revamp their rotation.”

With the Cubs needing pitching help, it makes sense that they are being viewed as a fit for Gray. He would give their starting rotation a significant boost if they signed him. Thus, they could be a team to watch very closely in the Gray sweepstakes this winter.

Bringing in a veteran pitcher like Gray would be massive for the Cubs. They are looking to be true contenders in 2027, and signing Gray could help them take another step in the right direction toward doing just that.


Looking at Gray

Boston Red Sox v Baltimore Orioles
GettyBALTIMORE, MD – SEPTEMBER 05: Sonny Gray #54 of the Boston Red Sox pitches against the Baltimore Orioles during the sixth inning at Oriole Park at Camden Yards on September 5, 2026 in Baltimore, Maryland. (Photo by Scott Taetsch/Getty Images)

Gray was fantastic for the Red Sox this season. In 29 games, he posted an 18-5 record, a 2.72 ERA, and 149 strikeouts. With this, the 5-foot-10 righty made his third-career All-Star Game.

With how well Gray pitched this season, it would not be surprising at all if the Cubs pursue him. These kinds of numbers are very impressive, and Gray would give Chicago’s rotation a significant boost if signed. Thus, they should be among the teams heavily targeting Gray this offseason.

While Gray will be in his age-37 season in 2027, the Cubs should not be afraid to target him. He would be such a strong pickup for the front half of their rotation. Due to this, the Cubs should make him one of their primary targets this offseason.

In 368 career MLB games over 14 seasons, Gray has posted a 143-107 record, a 3.51 ERA, and 2,074 strikeouts. He has had a great career, and that should only make the Cubs more intrigued about the possibility of signing him. It will be interesting to see if they end up being the team that signs him this offseason from here.

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Chicago Cubs Predicted to Sign Red Sox 18-Win Star Pitcher in Major Move

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