Cubs have an easy Jacob Webb contract decision despite his frustrating finish

There may be turnover aplenty coming for the Chicago Cubs next year, but one place where they'll have a surprisingly solid foundation is the bullpen. Caleb Thielbar, Hunter Harvey, and Aaron Civale will all hit the open market, but otherwise, much of the same crew will be in place. Daniel Palencia is still under contract, Phil Maton will have a chance at redemption in the second year of his deal, and Ryan Zeferjahn has a lot of control left after the big trade deadline deal with the Angels. Those three alone create a decently high ceiling at the back end, albeit with some risk.

After that, Ryan Rolison is only just hitting his first year in arbitration. He's due a modest raise after a 3.14 ERA and 3.94 FIP season, but he gives them another solid returning piece. Assuming fewer injuries this time, Javier Assad and potentially Colin Rea, if his option is picked up, will then add depth as long-relief swingmen. Jed Hoyer can then lean on a mix of lower-end to minor-league reclamation projects, with, perhaps, a bigger swing on a higher-dollar reliever, with some confidence in what he has already locked up.

Before worrying about free-agent or trade additions, however, there's the matter of Jacob Webb. There's no denying he had a rough end to the season. Starting when he gave up the walk-off home run to Randy Arozarena on Aug. 22, he threw 10 innings with a 9.90 ERA through the rest of the regular season, including three two-run, game-tying or walk-off blasts in a row. Even though he made some ugly history, that shouldn't stop the Cubs from picking up his $2.5 million club option without thinking twice.

There's a case to be made that Webb gave the Cubs one of the best seasons of his career in 2026. In a high of 67 innings, he posted a 3.36 ERA with a 4.03 FIP, though his expected ERA was comfortably the worst of his career at 4.35. However, his home-run-to-fly-ball ratio was above 15%, suggesting he got a bit unlucky whenever the ball was hit in the air. With that in mind, his expected FIP was by far the lowest of his career at 3.57. Under the hood, his 25.7 percent strikeout rate was also a personal best, and his 33.3 percent whiff rate was in the 96th percentile of all pitchers.

The Cubs could get the best of Jacob Webb outside of high leverage

It's fair to wonder if Webb's rough stretch was the result of overusage. Injuries to Palencia, Maton, Harvey, and more forced him into the closer role in the middle of the season, where he mostly thrived, posting a 24-game scoreless streak, but eating up a ton of innings in the process. Despite being a lower-cost signing brought on with some risk, he ended the year with nine saves as he became one of Craig Counsell's only go-to relievers. It wouldn't be the first time the Cubs have seen the adverse effects of riding specific arms into the ground out of necessity.

Having Webb in a middle-relief or setup role where he's not needed nearly as often would do more to maximize his effectiveness and keep him sharp until the end of the season. Even if he repeats what he did in 2026, or comes close to it, $2.5 million would be a bargain given the usual cost of pitching in the offseason. The fact that he can, in theory, step into higher leverage makes the decision even easier. Though if the Cubs could go one step further and add someone like Adrian Morejon or David Bednar to lessen the chance that's required, it would give this unit upside it simply hasn't enjoyed in recent years.

This isn't a case like Andrew Kittredge's last year, when he had a $9 million option heading into his age-36 season. Webb will be 33 next year and has been fairly consistent, only once having an ERA of 4.00 or higher in a season. Walks can be a slight problem at times, and he has faced issues with the long ball, but he brings solid swing-and-miss and potential to step up when he's needed most for an arm at that price. Add in the fact that he's respected in the clubhouse by his teammates and manager, and it should be a slam-dunk move for the Cubs.

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