Chicago Cubs tied to $157 million possible pitching power grab this winter

The Chicago Cubs, if they’re serious about making a deep playoff run in 2026 and possibly even having a chance at a championship, need to get serious about their pitching.

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Being serious means that they have to stop shopping exclusively in the bargain bin, looking for reclamation projects and fringe arms on a budget, gambling on pleasant surprises. The Cubs were very fortunate last season that the bet on Matthew Boyd paid off and that Cade Horton came up from the minors to have a remarkable run in the starting rotation. Colin Rea also performed above expectations in 2025.

If things had played out according to reasonable expectations from Boyd, Horton, and even Rea, Chicago may have finished lower in the standings and nowhere near a playoff spot.

This coming season, the team can’t count on Boyd and Horton– two players with significant histories of injury– to replicate last season’s success and Rea, by all accounts, may find himself in the bullpen, working long relief and spot starting. Shota Imanaga, meanwhile, may be gone altogether, after the Cubs declined his option.

Pitching as the primary focus

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Sure, Justin Steele is due back from elbow surgery at some point in the season. But the Cubs are going to need much more than half-a-season of a rehabbed Steele and crossed fingers that everyone else holds up. They’ll also, by the way, be tasked with rebuilding almost their entire bullpen. That’s why the team, itself, has declared pitching it’s primary focus this winter.

“We’re gonna have an active offseason,” president of baseball operations Jed Hoyer told reporters at the GM meetings in Las Vegas. “Take that for what it’s worth. I think the largest focus will be on pitching; I think that’s obvious looking at our depth chart. We’re in pretty good position on the position player side; on the pitching side, we’re thinner.”

Tim Kelly of Bleacher Report is taking Hoyer at his word and predicting that the Cubs will actually go deep in their free agent spending, specifically when it comes to starting pitchers.

Targeting an ace as well as a veteran?

First, Kelly projects the Cubs to land lefty ace Framber Valdez, formerly of the Astros.

Per Kelly:

“The Cubs probably need to find a way to add multiple impact starters to go with Matthew Boyd and Cade Horton. Framber Valdez would be a good name to start with…

Since the start of the 2022 season, Valdez is second among all starters in innings pitched (767.2) and fifth in WAR (16.5), per FanGraphs…

Valdez is not without faults as a free agent. First of all, he’s entering his age-32 season, so he’s a couple years older than some of the other arms available this winter, such as Suárez, Cease and Gallen. Secondly, while he was an All-Star this past year, he struggled in the second half of the season, posting a 5.20 ERA after the Midsummer Classic.”

Kelly estimates the Valdez contract at $114 million over four years with a $25 million club option for 2030.

The analyst also ties the Cubs to right-hander Lucas Giolito, as the veteran’s fall-back option behind the Yankees. He estimates the free agent contract of the former White Sox mainstay to be two-years at $43 million with a $20 million club option for 2028. The 31-year-old had a bounce back year in 2025, posting a 3.41 ERA over 26 starts after three consecutive seasons full of injury and inconsistency.

A rebuilt Chicago Cubs starting rotation

Adding Valdez and Giolito to the Cubs’s starting five would certainly signify a major shift in club philosophy regarding spending on pitchers. It would also fortify the rotation ahead of 2027 when Boyd and Jameson Taillon could be gone via free agency.

A rotation of Valdez, Boyd, Horton, Taillon, and Steele, with Giolito worked into the mix somewhere, would be elite. It would also free up names such as Javier Assad and Ben Brown to be moved via trade for bullpen talent and/or a quality role player for the bench.

But banking on the Cubs spending $157 million for six years of pitching reads a little like fan fiction, given the team’s historically frugal ways. Maybe one or the other could be signed, with hopes and prayers affixed to them targeting Valdez over Giolito. But, even then, it’s hard to be optimistic.

Maybe the team’s big pitching acquisition will come via trade, as rumored. Maybe they’ll just fall back on working the fringes of free agency, looking to grab the right arm at the right time for the most team-friendly contract. As always, time will tell.

The post Chicago Cubs tied to $157 million possible pitching power grab this winter appeared first on ChiCitySports.

Source: https://www.chicitysports.com/chicago-cubs-valdez-giolito-free-agents-2026