Whenever the Chicago Cubs open the 2027 season, we shouldn’t expect to see Tarik Skubal emerging from the Wrigley Field ivy like it’s a cornfield in Iowa.
The Athletic’s Sahadev Sharma reported on Monday that the Cubs, who are fresh off an NL Wild Card Series loss to the Padres, are not expected to pursue Skubal in free agency. They’ll instead prioritize pitchers with a high ground ball rate or a high strikeout rate; reunions with David Peterson and Clay Holmes, both of whom recently hit free agency, make sense in that regard.
But where else could the Cubs turn? For this list, we’re looking solely at external options, so we’ve excluded the trio of Peterson, Holmes and Shota Imanaga. For what it’s worth, though, we personally view Holmes as the best of those three options, so do with that what you will.
Let’s start by looking at one of Holmes’ ex-teammates, albeit one who has never pitched outside of the AL East.
5. Clarke Schmidt, New York Yankees (trade)
Would the Yankees really trade Schmidt, who turns 31 in February and is entering his final season of team control? We certainly would, even after Tommy John surgery cost him nearly the entire 2026 season. That said, the 2017 first-round pick returned in time for the postseason and is expected to be a full go whenever spring training begins.
Although the Yankees could keep Schmidt as a possible sixth starter or transition him into a “fireman” role, they lose nothing by fielding trade inquiries. Schmidt had a 3.07 ERA and allowed only 17 home runs over 164 innings from 2024-25, and he’s obviously fully familiar with pitching for a major-market team.
4. Michael King, San Diego Padres (free agent)
King quietly turned in another impressive season for the Padres, recording a career-high 4.3 bWAR and holding opponents to a .653 OPS in 185 innings. You’d be taking a slight age risk with him turning 32 next spring, and he’s hitting unrestricted free agency at the perfect time — assuming, of course, that the veteran righty signs before the work stoppage.
We actually really like King, and we prefer him to Freddy Peralta, who we’ll cover shortly. But Peralta is a year younger and has a far greater track record as a starter, so King earns the No. 4 spot. Tough luck, at least until he puts pen to paper.
3. Freddy Peralta, Tampa Bay Rays (free agent)
Peralta only placing third on our list isn’t solely because he could command a $100 million deal on the open market. His control issues plagued him throughout his 22 starts with the Mets, and he allowed 10 walks in 21.1 postseason innings, though we conveniently forget the latter because he won ALCS MVP.
Then, there’s the workload concerns. Maybe we’re old school, but we’re not overly impressed by Peralta averaging less than six innings over the last four years. If you’re the Cubs, do you want to guarantee nine figures to a pitcher entering his age-31 season? Hard pass, even if Peralta previously pitched for Cubs manager Craig Counsell in Milwaukee.
2. Nick Pivetta, San Diego Padres (free agent)
Pivetta realistically profiles as a No. 3 starter at best, and the right elbow flexor strain that cost him much of the 2026 season might intimidate Cubs fans. We get it, and we understand your frustration. Pursuing someone who turns 34 in February rather than targeting Skubal comes with its own issues … and yet, we wholeheartedly support this potential partnership.
Don’t read too much into Pivetta’s injury, especially considering that he returned in time for the postseason. He averaged 2.8 bWAR and 161 innings from 2021-25, and those are exactly the numbers any contender will happily take from a middle-of-the-rotation starter. We imagine he’ll come relatively cheap, at least in terms of contract length.
1. Sonny Gray, Boston Red Sox (free agent)
In some ways, this would be an unexpected reunion; the Cubs took Gray in the 2008 draft’s 27th round, though he elected to instead attend Vanderbilt and become a mainstay in the Commodores’ rotation.
Gray just turned 37 and is coming off a resurgent season, with his 4.3 bWAR and 2.72 ERA marking his best since 2023. The Cubs would be signing him knowing he’s potentially a rental, but he’s familiar with the NL Central and remains incredibly durable. By no means is he a superior option to Skubal, but we value his ability to go six innings and limit the free passes; his 6.7 percent walk rate was considerably below his 7.7 percent lifetime average.
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