Cubs Put Their Sights on Tarik Skubal After Bringing Back Veteran Bullpen Arm Amid Free Agency

The Chicago Cubs have already started making noise in free agency, beginning with a familiar bullpen arm. Jacob Webb has agreed to return on a 1-year, $2 million deal, with a $4 million team option for 2028. This move, added to the Tarik Skubal rumor, shows that the Cubs are going into the market to solve the problems their pitching had in 2026.

“The Chicago Cubs badly want Skubal,” said Jeff Passan when asked about Tarik Skubal’s free agency.

Jacob Webb recorded 73 strikeouts, 9 saves, and a 3.36 ERA across 67 innings. He also delivered a 24-game scoreless stretch when the bullpen needed stability. His return addresses one concern, but Chicago’s bigger challenge remains rebuilding its starting rotation. That is where Skubal’s reported interest becomes significant, although his expected price could complicate Chicago’s pursuit. For a team searching for pitching answers, the decision could shape its entire offseason.

His free-agent market is expected to pass $300 million, with some reports suggesting it could approach $400 million. The Cubs have spent heavily before, but their largest free-agent contracts remain below that projected figure. Jason Heyward received 8 years and $184 million, while Dansby Swanson signed for 7 years and $177 million. Alex Bregman’s $175 million deal also shows Chicago’s willingness to invest, but Skubal’s price could demand something different.

There is a reason the Cubs are considering such a major commitment after their 2026 season.

Chicago finished 89-73, but its pitching staff posted a 4.12 ERA and allowed 231 home runs. Those numbers reflected a group that struggled to prevent damage and deliver steady performances. The rotation also lacked stability, as Chicago used 14 different starting pitchers throughout the season. Shota Imanaga led the staff with 32 starts and 174.1 innings, carrying much of the workload.

However, injuries repeatedly forced Chicago to search for replacements and adjust its plans. Matthew Boyd made only 22 starts, while Cade Horton underwent right elbow surgery in April. Justin Steele and Ben Brown also dealt with major injuries that limited their availability. Imanaga allowed 35 home runs, while Kevin Gausman finished with shoulder trouble after arriving from Toronto.

The rotation never looked settled, leaving the Cubs with difficult questions throughout the season.

Those problems also followed Chicago into October, when the Cubs were swept by San Diego. They lost 8-0 in Game 1 before falling 4-1 in Game 2. Boyd surrendered 4 runs across 4 innings, while Gausman allowed 3 runs in 3.1 innings. The Padres also hit 4 home runs across both games, exposing Chicago’s struggles against power. For Cubs fans, the postseason ended with another reminder that the pitching staff needed serious attention.

Now, the offseason brings another concern, as several important pitchers could leave through free agency. Imanaga, Boyd, Holmes, Gausman, and David Peterson are among those facing uncertain futures. Their departures could remove much of the rotation Chicago relied upon during its playoff run. President of baseball operations Jed Hoyer has already made pitching a central priority.

“The great majority of our focus this winter is going to be on pitching acquisition,” Hoyer said.

Hoyer also acknowledged the staff’s broader shortcomings, saying, “The overall quality of the pitching has to improve.”

The Cubs have started addressing those concerns, but their rotation still needs major changes. Skubal’s reported availability gives the Cubs a chance to pursue an established ace. Whether the Cubs are willing to pay the price remains the biggest question.

How Tarik Skubal will solve many problems with the Cubs’ pitching department

The Chicago Cubs have made pitching a priority this offseason, and Tarik Skubal could be the answer to their biggest concerns. The Cubs finished 2026 with an 89–73 record, but their pitching staff struggled to provide consistent results. Chicago posted a 4.12 ERA while allowing 231 home runs, exposing problems that became harder to ignore during October.

Now, with Skubal reportedly drawing serious interest from the Cubs, the team could pursue a move that changes its rotation. The reigning ace would bring more than another starting pitcher to Chicago.

Skubal’s recent numbers show why he could address several of those issues. He recorded a 2.72 ERA across 26 starts in 2026, striking out 186 hitters over 158.2 innings. His 30% strikeout rate and 4.4% walk rate reflect an ability to miss bats without surrendering unnecessary baserunners. The Cubs, meanwhile, allowed 1.44 home runs per 9 innings, leaving little room for mistakes. Skubal’s 0.79 home runs allowed per 9 innings could help limit that damage.

The rotation also faced questions about durability and depth throughout the season. The Cubs used 14 different starting pitchers, and injuries affected Cade Horton, Justin Steele, and Ben Brown. Skubal delivered at least 192 innings in both 2024 and 2025, giving the Cubs a proven workhorse at the front. His presence would not eliminate every injury concern, but it could reduce the pressure on the rotation’s less established options.

That stability matters for a team trying to make a deeper postseason run.

Signing Skubal, however, would require the Cubs to break their free-agent signing record. Their largest deal remains Jason Heyward’s 8-year, $184 million contract, while Skubal could command more than $300 million. That price would reflect his age, elite production, and ability to anchor a rotation. The Cubs have already shown they can build a competitive team, but their pitching shortcomings remain difficult to overlook. If they believe Skubal can turn those weaknesses into strengths, spending record money could be a calculated investment rather than an expensive gamble.

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