Chicago Cubs Predicted To Land World Series Champion Pitcher in Free Agency

The Chicago Cubs have been predicted to upgrade their starting pitching staff in a big way in free agency.

Oct 30, 2024; New York, New York, USA; Los Angeles Dodgers pitcher Jack Flaherty (0) reacts after being relieved during the second inning against the New York Yankees in game four of the 2024 MLB World Series at Yankee Stadium. / Brad Penner-Imagn Images

The Chicago Cubs don’t have too many glaring needs on their roster following the 2024 season.

With Cody Bellinger deciding to accept his player option for 2025, $27.5 million of potential money to spend went away. With him in the fold, there isn’t a pressing need in the lineup, except for maybe a catcher despite trading for Matt Thaiss.

That could change if the team is able to trade him away, as some reports have indicated they are looking to do.

Where the Cubs are going to focus their spending, which insiders believe will be limited by ownership, is their pitching staff.

Chicago revamped the bullpen this past year, as early struggles led to new players getting opportunities. Out of that, they have found some long-term pieces, such as Porter Hodge and Nate Pearson.

In the starting rotation, the team has already lost veteran Kyle Hendricks when he signed a deal in free agency with the Los Angeles Angels.

While his production slipped, he brought veteran leadership to the team as the longest-tenured player. An addition will have to be made to replace him, and it will be interesting to see how high in the market Chicago goes.

They have a strong quartet in place already with Shota Imanaga, Justin Steele, Jameson Taillon and Javier Assad, but Andy McCullough of The Athletic believes the perfect addition for the team in free agency would be to add Jack Flaherty to the mix.

“Flaherty made the most of his pillow-contract season in 2024. He logged more innings than he had since 2019, when he looked like a budding ace in St. Louis. He thrived in Detroit and became the No. 1 starter for the eventual World Series champions in Los Angeles. Flaherty would like to stay with the Dodgers, but they may have their sights set a bit higher. The Cubs could use some stability in the rotation,” he wrote.

He started the 2024 campaign with the Detroit Tigers after signing a one-year deal as a free agent. His production was excellent, as he was traded to the Los Angeles Dodgers ahead of the deadline and helped them win the World Series.

Now, he is in a position to land a lucrative multiyear deal, and McCullough believes the Cubs are the perfect team to give it to him.

Reports have swirled that the Cubs are already out on some of the bigger-named players on the market, as agents are not thrilled with how they are operating this offseason as a franchise in one of the largest markets.

Flaherty, who turned 29 in October, is younger than some of the other pitchers hitting the market, which could give him an edge in some regard.

He also performed at a high-level last season and helped anchor a staff that won the championship.