Brewers' division rivals' 2026 bullpen makeover continues with another strong signing

2025 saw a new chapter added to the Milwaukee Brewers and Chicago Cubs' heated rivalry; for the first time, the two division rivals squared off in the postseason. Adding to a recent history that includes the two teams facing off in an electric Game 163 to determine the 2018 winner of the NL Central and the fact that Craig Counsell left Milwaukee to manage the Cubs after nine seasons as the Brewers' skipper, the teams' 2025 postseason clash was one fans won't soon forget.

Since their memorable NLDS match-up, which Milwaukee won in five games, both the Brewers and Cubs have directed their attention to how each of them can topple the giant that is the Los Angeles Dodgers. Milwaukee's approach has been essentially keeping together their roster that won an MLB-best 97 games during the regular season last season, not needing to fix what isn't broken. However, such a strategy hasn't come cheap for Matt Arnold and the Brewers' front office.

To return veteran Brandon Woodruff, who was a key part of their rotation during the second half of the regular season, the Brewers offered their long-time fan favorite the $22.025 million qualifying offer, which he accepted. As a result, while the Brewers' roster might not look much different than it did during their record-breaking 2025 campaign, it has required Milwaukee to approach record highs in regard to their Opening Day payroll, a development that should excite fans who have long been calling for the organization to spend more money.

Meanwhile, down in Chicago, the Cubs' offseason strategy has mostly focused on shoring up the part of their roster that saw the most departures at the end of the 2025 campaign: the bullpen. The Cubs have already officially lost Andrew Kittredge, Brad Keller, Mike Soroka, and Drew Pomeranz this winter, all of whom were a part of their NLDS bullpen. Additionally, Taylor Rogers, who the Cubs added at the trade deadline but wasn't included on their NLDS roster, is a free agent this winter and still searching for his next opportunity.

Chicago has signed five free agents to major league deals this offseason, and four of them are relief arms. Prior to Tuesday, the Cubs had already signed Phil Maton to a two-year, $14.5 million deal, added former Brewers Hoby Milner on a one-year deal, and re-signed Caleb Thielbar on a one-year pact as well. Yesterday, they added another intriguing arm to the mix, fortifying what is becoming a formidable bullpen group.

Cubs add veteran reliever Jacob Webb on a one-year deal, contuining their run of relief pitcher signings

The Cubs aren't shopping for top-tier relief pitcher talent like Edwin Díaz, Devin Williams, or Robert Suárez like their fans want them to, but that doesn't mean they aren't adding strong arms to their 2026 bullpen. Cubs' President of Baseball Operations, Jed Hoyer, isn't one to spend big on relief pitching, opting instead to add veteran relievers on short-term deals who have the ability to be very effective bullpen arms when used in the right roles.

Maton's deal looks like one of the better ones signed by a relief pitcher this offseason, and Milner and Thielbar offer value as reliable, left-handed arms who each made more than 65 appearances during the 2025 season. Now add to that group Webb, who is joining his fifth MLB organization in his seventh season in MLB. Outside of a stellar rookie campaign with the Atlanta Braves back in 2019, Webb posted the best season of his career in 2025, as a member of the Texas Rangers.

With a 3.00 ERA on the dot in 55 appearances, Webb was the bright spot in an otherwise shaky Rangers bullpen. Even with a FIP of 4.30, Webb's sparkling 1.030 WHIP in 2025 tells a story of a relief arm who found a new level in his age-31 season. Where Webb excelled was inducing weak contact. With an average exit velocity, barrel rate, and hard hit rate that each ranked in the 85th percentile or higher, Webb's specialty is not missing bats, with pedestrian whiff and strikeout rates to prove it, but rather missing barrels.

It's a three-pitch mix for Webb, one that doesn't include overpowering or particularly nasty offerings, but he locates his fastball, sweeper, and changeup well, which allows him to get by even with a four-seamer that averaged just 93.4 mph a season ago.

Though Webb doesn't have an All-Star appearance or a big salary to prove his abilities, he's certainly another solid addition to Chicago's bullpen, signaling to Brewers fans and the rest of the baseball world that the Cubs are content making strong under-the-radar signings in their bullpen this offseason, which could suggest a larger move is on the horizon. Chicago has yet to spend significant money on a single player this offseason, but they absolutely can afford to do so before the 2026 season arrives. That said, even with a major signing of, say, Japanese ace Tatsuya Imai or even a reunion with Kyle Tucker, which doesn't seem likely, Chicago has a lot to prove if they want to topple the back-to-back-to-back NL Central winners, the Milwaukee Brewers.