Chicago Cubs Should Target Los Angeles Dodgers Starter in Free Agency

The Chicago Cubs could link up with the right-hander to return him to the NL Central.

Oct 25, 2024; Los Angeles, California, USA; Los Angeles Dodgers starting pitcher Jack Flaherty (0) reacts after giving up a two-run home run in the sixth inning against the New York Yankees during game one of the 2024 MLB World Series at Dodger Stadium. / Jayne Kamin-Oncea-Imagn Images

The Chicago Cubs had an opportunity to improve their team for 2025 at the deadline and did just that. While there were other options for them to pursue, the Cubs were limited in what they wanted to do due to certain players hitting free agency when the year ended.

Of those players included Jack Flaherty, who was traded to the Los Angeles Dodgers at the deadline.

Flaherty would've been an ideal piece to this rotation, but considering the right-hander will hit the open market, moving assets for him with the chance of him departing in free agency wouldn't have made much sense.

But the time is now to land Flaherty, as he'd be an intriguing piece to their rotation. Highlighting him as a right-hander is the most important aspect, and his potential price should allow Chicago to sign and trade for other contracts in the winter.

Jim Bowden of The Athletic predicted his future contract, which was worth $68 million for three years.

"Jack Flaherty was the best starting pitcher traded at the deadline after logging a 2.95 ERA with 133 strikeouts and 19 walks in 18 starts for the Tigers, who dealt him because he was an impending free agent and they didn’t think they were a contender... The Tigers had a preliminary trade agreement in place with the Yankees, but New York backed out of the deal over concerns about his medical records... He showed his ability to miss bats this season with 194 strikeouts (in 162 innings), his highest total since 2019, when he finished fourth in the NL Cy Young Award voting. He’s only 29. If teams aren’t concerned about the medical risk associated with his back issues, he should land a three-year pact."

As Bowden touched on, there are concerns about Flaherty's medicals. He had a back issue, but throughout the campaign, it didn't seem to be too big of an issue.

He was once regarded as an up-and-coming arm in Major League Baseball but had a few rough years before reviving his career this season.

For the Cubs, paying an arm of his caliber about $22 million a year shouldn't be too much of an issue. Even if he isn't as elite as was in 2024, there's reason to believe he could, at worst, be the No. 3 in this rotation.

Flaherty's strikeout stuff is reason for optimism, as pitchers who post 194 strikeouts in 162.0 innings typically find long-term success.

Chicago would be wise to give him a chance and have him return to the NL Central.