Cubs Bolster Bullpen with Jacob Webb Addition Ahead of 2026 Season
As Chicago looks to build on a deep 2025 playoff run, the Cubs have signed reliever Jacob Webb, adding to a winter of bullpen upgrades aimed at avoiding another early postseason exit.
- Glenn Catubig
- 3 min read
The Chicago Cubs came up short of a World Series return in 2025, advancing past the Padres in the NL Wild Card before falling to division rivals Milwaukee in a hard-fought NLDS. Despite pushing the Brewers to the limit, Chicago’s season ended earlier than hoped, prompting a roster reevaluation by the front office.
On Tuesday, multiple reports confirmed the Cubs’ signing of reliever Jacob Webb, a move aimed at strengthening a bullpen that struggled at key moments last season. Webb joins a growing list of acquisitions designed to give manager Craig Counsell a deeper, more reliable late-inning corps.
According to The Athletic’s Will Sammon, Webb’s contract for 2026 is set at $1.5 million, with incentives pushing it to $2 million. An option for 2027 could be worth $2.5 million, with potential incentives elevating it to $3 million. The signing reflects Chicago’s strategy of blending cost-effective contracts with performance-based rewards.
Webb marks the third former Texas Rangers reliever to join the Cubs this offseason, following the additions of Phil Maton and Hoby Milner. Together, the trio represents a targeted effort by president of baseball operations Jed Hoyer to address the team’s bullpen depth ahead of another playoff push.
1. Revamping the Bullpen
Chicago’s bullpen has been a focal point this offseason, as the Cubs look to avoid repeated late-season collapses. Webb, Maton, and Milner collectively provide a mix of experience, versatility, and strikeout potential. Webb’s arrival offers a reliable arm for high-leverage situations. His track record in relief roles demonstrates an ability to get outs in critical moments, a skill the Cubs will rely on in close postseason contests. Maton and Milner complement Webb by providing innings depth and matchup flexibility. Chicago’s approach emphasizes not only replacing lost arms but creating a bullpen that can adapt to multiple situations, from starters struggling early to tight playoff scenarios. By aggressively addressing these needs now, Hoyer aims to ensure the Cubs have the late-inning firepower to compete against teams with deeper pitching rosters, like Milwaukee.
2. Supporting Roster Moves
The Cubs’ offseason has extended beyond pitching, with additions designed to enhance lineup flexibility. First baseman Tyler Austin returns to MLB after a stint in Japan, while utility player Scott Kingery joins as a non-roster invitee to spring training. These moves provide depth across multiple positions, giving Counsell more options to manage injuries or rest starters over a long season. The additions also complement the team’s emerging core of younger players, ensuring the roster can withstand the demands of a playoff run. Meanwhile, former Chicago outfielder Kyle Tucker remains a free agent, along with ex-Cub Cody Bellinger. While the team could pursue either bat, Hoyer appears content focusing on cost-effective alternatives that fit within the team’s overall payroll and developmental strategy. The combination of bullpen upgrades and roster depth aims to address last season’s shortcomings, positioning Chicago for a more sustained postseason campaign in 2026.
3. Looking Ahead to 2026
While the Cubs have shored up key areas, questions remain about whether these moves are sufficient to compete with deeper NL Central rivals. A revamped bullpen will help, but Chicago will also need consistent offensive production and starting pitching stability to avoid another early exit. Hoyer’s strategy emphasizes a balanced approach, blending low-risk veteran signings with opportunities for younger players to contribute. This approach allows the team to maximize flexibility while preparing for both immediate and long-term success. Spring training will provide an early indicator of how these pieces fit together, particularly Webb’s integration into the bullpen hierarchy. Performance in April and May could determine the team’s readiness to contend down the stretch. Ultimately, Chicago’s offseason moves signal a commitment to learning from last year’s playoff shortcomings and giving Counsell the tools necessary to make a deeper run in 2026.