The Boston Red Sox made the postseason this year, but their starting rotation could look very different next season. Garrett Crochet was the ace the Red Sox needed, but now he needs some more help.
Behind Crochet, Brayan Bello and Lucas Giolito were solid starters. However, Craig Breslow has expressed a desire to add to the rotation, noting the team would only make a move for a pitcher who can pitch near the top of the Red Sox rotation. Bello is under contract, but Giolito is a free agent after declining his $19 million mutual option.
Giolito had a resurgent season, but between his free agency, injury history and Breslow’s desire to add to the top of the rotation, Giolito could sign elsewhere. Bleacher Report’s Tim Kelly predicted Giolito would sign with the Chicago Cubs.

“Two years is probably the ceiling Giolito will get in terms of guaranteed seasons,” wrote Kelly. “A return to Chicago—this time on the north side—could make sense, though the Cubs might shoot higher to open the winter.”
Kelly predicted Giolito to sign a two-year, $43 million deal with a club option for 2028. He signed with the Red Sox before the 2024 season, but underwent elbow surgery in the same offseason. He was an All-Star in 2019, but had a 4.31 ERA in three seasons after. Last season, he had a 3.41 ERA in 26 starts.
Giolito could be a great fit with the Cubs after his bounce-back season. It was his best year since his lone All-Star season, and the Cubs have a need. Shota Imanag is a free agent and Justin Steele is recovering from season-ending surgery. Giolito could slot in as one of the Cubs’ better starters right away.