The Cubs have settled Jacob Webb’s future for 2027, and they did it on terms that give the bullpen a little more certainty - and a little less cost.
Instead of simply exercising Webb’s $2.5 million option for the 2027 season, Chicago and the right-hander agreed to a one-year deal worth $2 million, according to FanSided’s Robert Murra y. The new contract also includes a $4 million club option for 2028 with a $500,000 buyout. That means the Cubs shaved $500,000 off the immediate price tag, a modest savings, but still a savings.
Webb’s 2026 season wound up being a useful one for the Cubs, even if it didn’t finish cleanly. With Daniel Palencia battling injuries throughout the year, Webb stepped into the de-facto closer role during the summer. He finished with a 3.36 ERA over 68 appearances and collected nine saves.
The late-season stretch was rougher. Webb blew three straight saves at the end of August and into September, a skid that dimmed the shine on his year and also underscored how thin the Cubs were in the late innings.
That shortage was a theme all season. Palencia’s injuries left a hole, and Jed Hoyer’s bullpen construction didn’t produce enough reliable high-leverage answers. Phil Maton spent the entire season dealing with a knee injury and wasn’t effective when he did pitch, while Hunter Harvey appeared in only four games for the Cubs.
Craig Counsell was left to use Webb in a role that hasn’t really been his calling card for most of his career. Webb has mainly worked as a middle reliever, and while the move brought some early success, the season eventually made it clear that he’s probably best suited to the middle innings.
The encouraging part for Chicago is that this winter doesn’t look like a total rebuild of the relief corps. Last offseason, Hoyer had to piece the group together from scratch.
This time, the Cubs already have a core in place for 2027 with Palencia, Ryan Zeferjahn, and Ryan Rolison under control. There’s also an expectation that Maton should be healthy - and better - next year.
Shelby Miller is another name to watch. He was shut down before he could pitch for the Cubs in 2026, but he enters the offseason healthy and ready to take on a bullpen role when the season begins.
Even with Webb back in the fold, the Cubs would still be wise to add another high-leverage arm. The group is more stable than it was a year ago, but Chicago still needs enough depth to keep anyone from being pushed beyond what they can handle.
In Other News...
Cubs May Finally Have A Bold Answer For Their Ninth-Inning Problem
The Cubs are heading into a winter where the bullpen sits near the top of the shopping list, and the timing matters with a December lockout looming. Chicago has been expected to attack both relief help and starting pitching, and one name that has started to surface in that conversation is Adrin Morejn, the left-handed Padres reliever whose recent run and age make him an intriguing fit for a club looking to stabilize the late innings.
Morejn is not a finished deal, but the idea has gained enough traction to stand out because of the kind of contract some around the game think he could command. For the Cubs, the appeal is obvious: a pitcher with closer upside, left-handed balance and enough upside to potentially reshape how the ninth inning looks in Chicago. Whether the front office is willing to go that far is the real question, and it is one that could define how aggressive this offseason becomes. [Read more 🡒]
Phillies Outfield Search Is Suddenly Centered On One Crucial Choice
The Phillies are headed into the offseason with a clear need in the outfield, and the market is already taking shape around a few familiar names. Among the free-agent options drawing attention is Ian Happ, whose profile naturally stands out because of his steady production and the kind of left-handed balance a contender can use. Taylor Ward and Tyrone Taylor are also in the mix as Philadelphia weighs both upside and fit while trying to patch a spot that has not held up well enough.
Happ, in particular, gives the Phillies a decision point that goes beyond simple need. He brings a track record that makes him easy to picture in a lineup built to win now, but any pursuit will come down to how aggressively Philadelphia wants to shop at the top of the market versus spreading its resources around the roster. No moves have been made yet, which leaves the club with options and a lot of room for the conversation to keep evolving. [Read more 🡒]
Mariners Saw Something In Former Astros Coach Fans Should Notice
The Mariners made a notable change after the 2026 season, moving on from Dan Wilson and turning to Jason Kanzler to lead the club beginning in 2027. For Cubs fans, Kanzler is a familiar name from his time as Chicagos director of player development, and Seattles decision says plenty about the kind of manager the organization believes can shape its next era.
Kanzler also brings a background as a former outfielder and a coach with the Astros, which helps explain why Seattle saw him as more than just another candidate. Mariners president of baseball operations Jerry Dipoto pointed to Kanzlers intelligence, intensity, creativity and ability to develop young players as traits that can help build a championship standard, a profile that should resonate with anyone who watched his work in Chicago. [Read more 🡒]