The Chicago Cubs may have to get creative this winter, because the top of the pitching market is already looking more like a dead end than a shopping spree.
Tarik Skubal’s contract demands have cooled that idea, and long-shot pursuits of Freddy Peralta and Michael King don’t exactly make the picture brighter. That leaves Jed Hoyer trying to rebuild a starting rotation that probably needs three quality additions, and the Cubs can’t just wait around and hope the answers arrive later. A major upgrade could still come through a trade, but free agency has to supply some help too.
If the Cubs decide the splashier arms are coming elsewhere and the free-agent market is mainly for depth, there are a few bargain names that fit that lane.
Walker Buehler is one of them. The Cubs have been tied to him more than once over the last few years, though nothing has ever materialized.
This time might be different. Buehler, a former World Series champion with the Los Angeles Dodgers, got off to a rough start with the San Diego Padres in 2026 before settling in down the stretch.
Over his final 13 appearances, he put up a 3.62 ERA. His full line wasn’t pretty - 4.63 ERA, 131 Ks, 153 2/3 IP - but that’s the tradeoff when you shop in this part of the market.
Erick Fedde is another familiar name in Cubs circles. When the St.
Louis Cardinals designated him for assignment in 2025 mid-season, there was some thought Chicago might jump in. Instead, he landed with the Chicago White Sox last winter on a one-year deal.
Used in a swingman role, Fedde gave the South Siders useful innings, logging a 3.83 ERA over 141 innings with 15 starts and 18 relief appearances. Since returning from Korea in 2024, he’s bounced through the Braves, White Sox, Cardinals and Brewers, posting a 4.13 ERA.
He’s not likely to duplicate his 5.6 bWAR breakout from 2024, but he could still be steady backend depth.
Lucas Giolito also remains out there after the San Diego Padres declined their end of a 2027 mutual option following his elbow injury that wiped out the second half of the season. He’s one year removed from a strong run in Boston, where he posted a 3.41 ERA across 145 innings, and he’s still just 32.
Giolito isn’t the Cy Young-level arm he once was with the White Sox, but if he’s healthy, he could still profile as a solid No. 3.
The bigger question is whether the Cubs are aiming any higher than mid-rotation help.
Chris Paddack rounds out the group, and his 2026 season was a mess. He went from the Marlins to the Reds to the Rangers before finishing the year in Korea.
There, he found something again, putting up a 2.95 ERA in the regular season and helping the Lions win the Korean Series. That kind of rebound could make him appealing to a team like the Cubs, who have shown a willingness to bet on reclamation projects.
And in Paddack’s case, the appeal is obvious: a low price tag and a chance at more than that.
In Other News...
Cubs Outfield Picture Is Taking Shape Around One Intriguing Name
The Cubs outfield is one of the more interesting roster puzzles on the board this winter, with Pete Crow-Armstrong already locked into center and two more spots suddenly in play. Ian Happ and Seiya Suzuki are both headed for free agency, which has opened the door for a different kind of conversation around the rest of the roster, including whether the answer might come from inside the organization rather than from outside additions.
Among the internal names, Pedro Ramirez has emerged as the most intriguing one to watch. GM Carter Hawkins has pointed to Ramirezs athleticism and versatility, traits that fit the kind of flexibility the Cubs may need as they sort through the outfield mix. Matt Shaw and Kevin Alcantara are also in the conversation, and the broader picture around the club keeps evolving with Jed Hoyers extension through 2030, the possibility of a Carson Kelly return, and a few notable front-office and player-development moves that show how much of the organization is being shaped at once. [Read more 🡒]
Cubs Still Need This Bat While Other Teams Start Moving
The Red Soxs decision to lock up Jake Bauers on a four-year, $56 million deal took one more name off the board for teams still sorting through their offseason plans, and it offered a reminder of how quickly the market can move once a club decides it wants a bat. Bauers had been viewed as a likely departure from Milwaukee after the Brewers extended him a qualifying offer, so Bostons move closes another door for contenders looking to add offense.
For the Cubs, the timing matters because their own offseason priorities remain unresolved and the lineup still needs help. Chicago has not made any significant moves yet, and every signing elsewhere only sharpens the pressure to find the right fit before the best options disappear. [Read more 🡒]
Cubs Are Eyeing A Brewers Pitching Project With Plenty To Prove
The Cubs have been doing their homework on Dustin May this offseason, and the right-hander fits the kind of low-risk, upside-driven arm teams often circle when they are trying to deepen a rotation. May has bounced around quite a bit, with stops that have included the Dodgers, Red Sox, Cardinals and Brewers, but Chicagos interest appears tied less to his recent rsum than to the raw stuff that still makes evaluators pause and look twice.
His time in Milwaukee left plenty of questions, especially after he posted a 5.65 ERA in 10 starts before being pulled from the rotation. Even so, the Cubs are said to be weighing him as a possible third addition to their 2027 starting mix, betting that his fastball velocity and extension numbers can still make him a worthwhile project if the rest of the package comes together. [Read more 🡒]