Cubs Have Easy Decision To Make About Jacob Webb

There are some decisions that the Chicago Cubs and their players will have to make before free agency officially begins in a few weeks. 

Will the Cubs extend the qualifying offer to Seiya Suzuki and/or Ian Happ?

Will Clay Holmes decline his $12 player option?

Will Matthew Boyd and/or Carson Kelly decline their mutual options? 

Some of those decisions are on the tougher side, while some are easy to see coming. The Cubs are expected to extend the qualifying offer to Suzuki, but they'll have to decide what to do with Happ. Holmes, Boyd, and Kelly will likely decline those options on their ends. 

However, there is one decision that the Cubs will have to make this offseason that is rather easy. The front office will have to decide whether to pick up Jacob Webb’s $2.5 million club option or decline it and let him test the free agent market. 

The Cubs will obviously pick up Webb’s option for the 2027 season. 

Webb put together another strong all-around campaign in 2026. He posted a 3.36 ERA, 1.254 WHIP, 73 strikeouts, and nine saves across 67 innings pitched. That sub-3.40 ERA marked the third straight season that the right-hander has finished below that ERA mark. 

In 2024, Webb had a 3.02 ERA and 58 strikeouts across 60 appearances with the Baltimore Orioles. In 2025, he had a 3.00 ERA and 58 strikeouts across 55 appearances with the Texas Rangers. This past season, the 33-year-old pitched in a career-high 68 games. 

Webb was really the Cubs' most consistent reliever throughout the year. He started the year as a setup man to Daniel Palencia before moving to that closer role once Palencia went on the injured list with a flexor strain. 

Now there was a rough stretch from Webb later in the 2026 season. From August 22 to September 15, the veteran right-hander allowed 11 earned runs across 6 ⅔ innings pitched (14.85 ERA). He gave up multiple runs in five of those eight appearances and eventually lost the closer job in mid-September. 

Outside of that stretch, though, Webb was nails at the back end of the Cubs bullpen. He posted an elite 2.21 ERA with a 27.2% strikeout rate in his first 57 appearances and was a major reason why the team stayed afloat amid all its injuries in the middle of the season. 

Webb will certainly be back for the 2027 season.