Chicago Cubs linked to two high-end free agent starting pitchers by analyst

The Chicago Cubs are, at this late stage of the season, being given a 100% likelihood of making the playoffs. They are also 3.5 games ahead of the San Diego Padres when it comes to taking the Wild Card top seed, which would give them home field advantage through the three-game Wild Card series.

That doesn’t mean, however, that the front office isn’t eyeing next season and beyond.

Given the quality of this Cubs team and the holes that it needs to address, free agency will loom large in their future.

Free agency looms large in Chicago Cubs’ future

On the minus side, it’s looking more and more likely that four-time All-Star Kyle Tucker might be a one season-and-done asset after coming from the Houston Astros in a 3-for-1 trade this past offseason. With heavy-spending teams such as the Dodgers, Yankees, and Red Sox, among others, possibly in on the bidding, it seems that the frugal Cubs ownership may be outbid for the right fielder’s services.

On the plus side, though, there’s an opportunity for the under-budget Cubs to add some truly impactful free agent assets for the 2026 campaign.

Jackson Roberts of SI.com recently wrote a piece spotlighting the top 2026 free agents and where he believes they may be headed. He tied two quality starters to the Cubs (while also predicting that Tucker will sign with the Dodgers).

Two pitchers tied to the Cubs

The first name Roberts mentioned is former Cubs prospect and current San Diego Padre Dylan Cease.

Per Roberts:

“Don’t sleep on Cease’s potential to shift the power dynamics of the league next season. He may not have an impressive ERA this season (4.59 after Saturday’s start), but he’s the only pitcher in all of baseball to tally at least 200 strikeouts in each of the last five seasons.

It doesn’t seem likely that the Padres’ financial situation will allow them to retain the 29-year-old righty, but there’s a National League rival with money to spend who could really use a right-handed starter.”

Cease was curiously dangled over the trade market near this year’s trade deadline, but the trigger on a deal was never pulled. The 7-year veteran was also rumored to be on the trade market in the offseason.

Cease, who has a 3.88 ERA in 7 big league season, has spent a career going up and down when it comes to performance, alternating from elite-level to mid-tier performance in alternating years. This season has been one of the mid-tier years.

Also mentioned in connection with the Cubs was Jack Flaherty of the Detroit Tigers, who has a $20 million player option for the coming season and a 3.80 ERA over 9 seasons to certify his worth. The thought is that the 29-year-old may opt out of his contract and test the free agent market in search of a multi-year contract.

If he does that, Roberts feels that the Cubs could swoop in to sign him up:

“Flaherty hasn’t had his best season, posting a 4.69 ERA through 29 starts. The strikeouts are still there, though, and with only $20 million on the table if he accepts his player option, it feels more likely that he’ll bank on the market valuing him enough to squeeze out a multi-year deal.”

Logical or not?

The two right-handers, Cease and Flaherty, would be welcomed assets to any team, really.

The question with the Cubs is whether they’ll spend the money and commit to the contract years when they currently have Matthew Boyd, Shota Imanaga, Cade Horton, Jameson Taillon, Colin Rea, and Javier Assad on staff as starters, with Justin Steele coming back from elbow surgery at some point next season.

On the other hand, though, Boyd, Taillon, and Rea are due to be free agents after the 2026 season and there’s no guarantee on Steele being the same after his injury. Adding at least one more quality starter to the rotation wouldn’t be unwise.

For now, 2026 is speculation as this 2025 team attempts to make a deep playoff run.