The Cubs don’t have much mystery here: Jacob Webb’s $2.5 million club option should be an easy call.
That decision sits against a bullpen picture that already has some shape to it for next season. Caleb Thielbar, Hunter Harvey, and Aaron Civale are all set to reach free agency, but plenty of the group is still in house.
Daniel Palencia remains under contract, Phil Maton gets a chance to bounce back in the second year of his deal, and Ryan Zeferjahn still comes with plenty of control after the Angels trade deadline deal. Ryan Rolison is also entering his first year of arbitration after a season that included a 3.14 ERA and 3.94 FIP, while Javier Assad and possibly Colin Rea, if his option is exercised, can supply more depth as long-relief swingmen.
That gives Jed Hoyer a baseline to work with before the Cubs even get into the market for outside help. He can fill in around the edges with cheaper relief bets or take a bigger swing on a pricier arm, knowing there’s already a decent foundation in place.
Webb belongs in that group, and his ugly finish shouldn’t change the decision. He allowed the walk-off homer to Randy Arozarena on Aug. 22, then closed the regular season with 10 innings and a 9.90 ERA.
Three straight game-tying or walk-off two-run homers made the ending look as bad as it gets. But the full season tells a much better story.
In 67 innings, Webb put up a 3.36 ERA and a 4.03 FIP, while his expected ERA landed at 4.35, the worst mark of his career. The long ball hurt him some - his home-run-to-fly-ball rate topped 15% - but his expected FIP came in at 3.57, easily the best of his career. He also set a personal best with a 25.7 percent strikeout rate, and his 33.3 percent whiff rate ranked in the 96th percentile across all pitchers.
The real question is whether the Cubs asked too much of him. Injuries to Palencia, Maton, Harvey, and others pushed Webb into the closer role in the middle of the season, and he handled it for a while, including a 24-game scoreless streak. He also piled up innings while becoming one of Craig Counsell’s most trusted options, finishing with nine saves.
That’s exactly why the Cubs should be willing to bring him back, but also why they’d be smart to use him differently. In a middle-relief or setup role, Webb wouldn’t have to carry the same weekly burden, and that could keep his stuff sharper deeper into the season.
Even if he simply repeats his 2026 performance, $2.5 million is still a bargain by bullpen standards. And if he’s needed in higher leverage, he has already shown he can handle it.
This isn’t the same kind of decision the Cubs faced with Andrew Kittredge last year, when a $9 million option loomed over an age-36 season. Webb will be 33 next year, and his track record is steady, with only one season in which his ERA has topped 4.00.
The walks can creep up, and the home run issue is real, but the strikeouts and swing-and-miss are there. For that price, the Cubs should pick up the option without hesitation.
In Other News...
Cubs Face Another Winter Question As Key Insider Draws Interest
The Cubs are already navigating a winter of turnover, with Jared Banner moving on to become the Orioles' general manager and John Mallee surfacing in the Mets' search for a hitting coach. Now another familiar name from their organization is drawing outside interest, as Seattle reportedly weighs Cubs farm director Jason Kanzler for its managerial opening. It is the kind of back-office ripple that can matter as much as any on-field move, especially for an organization trying to keep its player development operation steady.
For Chicago, the timing only adds to the uncertainty. The Angels are also reshaping their front office and dugout, which can widen the market for candidates and create more movement around the league, while the Cubs continue to scout Japanese third baseman Teruaki Sato ahead of his expected posting this offseason. The question is whether there is a clean fit for him on the roster, but before that gets answered, the Cubs may have to sort through another winter issue closer to home: whether one of their important voices is staying put. [Read more 🡒]
Cubs Fans Should Watch One AL Contender Closely This Winter
After a run to the 2025 World Series, the Blue Jays are heading into an offseason with a few obvious holes to patch, and the offensive side of the roster looks like the place where they may be most aggressive. Among the names already tied to Toronto are two familiar to Cubs fans, Seiya Suzuki and Ian Happ, a reminder that a contender with financial muscle and urgency can quickly become part of the market for proven bats.
Torontos interest could make this winter more interesting for Chicago than it might seem at first glance. The Blue Jays need help at designated hitter and in the outfield, but the expected lockout and the kind of crowded free-agent bidding that comes with it could complicate their plans, leaving Cubs fans to watch whether the team that came so close to a title can actually turn that interest into a signing. [Read more 🡒]
Cubs Already Have A Tough Corbin Martin Decision To Make
Corbin Martins brief run with the Cubs looked promising at first. The right-hander gave Chicago four scoreless outings in his first stretch with the club and appeared to give the bullpen another useful arm before his command started to slip. Once the control problems piled up, the Cubs designated him for assignment and sent him back to Triple-A on May 10, a quick turn that underscored how little margin there was for error.
The harder part now is sorting out what comes next for a pitcher who never really got the runway to settle in. Martin kept working in the minors after the demotion, but his season was interrupted by an injury that cost him a long stretch down the line, leaving the Cubs with one more uncomfortable call to weigh on a depth piece who flashed enough early to make them notice in the first place. [Read more 🡒]