Cubs Unlikely To Pursue Tarik Skubal

The Cubs have the biggest rotation need of any ostensible contender as we enter the 2026-27 offseason, but having the biggest need apparently doesn’t entail pursuing the biggest name on the market. Sahadev Sharma of The Athletic reports that the Cubs will surely check in but aren’t planning to be real bidders for two-time American League Cy Young Award winner Tarik Skubal. While Chicago, in theory, should be able to spend with the top teams in the league, that’s never been the playbook for the Ricketts family ownership group. The Cubs have never given out a contract larger than Jason Heyward’s $184MM deal, which is now nearly 11 years old. The team is particularly cautious when it comes to pitching contracts. Jon Lester’s six-year, $155MM deal from the 2014-15 offseason is the largest in franchise history, and Yu Darvish’s six-year, $126MM is the only other $100MM+ contract the Cubs have given to a pitcher. Skubal, of course, is going to breeze well beyond all of those contracts. It’s all but assumed he’ll break Yoshinobu Yamamoto’s $325MM record for a pitcher — the primary question is one of “by how much” he’ll do so and not one of whether he’ll reach those heights at all. Beyond the fact that Skubal is going to be way north of the Cubs’ typical comfort zone, Chicago has such a wide-ranging need that dedicating so many of their resources to one arm could be limiting. The Cubs could saw all of Matthew Boyd, Clay Holmes, Kevin Gausman, Shota Imanaga, David Peterson and Colin Rea reach free agency following the season. Justin Steele hasn’t pitched since April 2025 due to UCL surgery and some slower-than-expected progress on his rehab. Cade Horton had UCL surgery this past April. Ben Brown and Edward Cabrera had injury troubles throughout the season. With so many arms needed to round out the rotation, it seems the Cubs will look to diversify their investment over several arms rather than make a run at one premier starter who’d leave them top-heavy. Of course, the Cubs could certainly afford to add Skubal and bring in another free agent and/or some help from the trade market. Young infielders Matt Shaw and Pedro Ramirez have both been frequently speculated trade candidates, and either could help the Cubs land a controllable, pre-arbitration arm. The Cubs have $110.25MM on next year’s books in terms of guaranteed contracts and option buyouts (as you can see in MLBTR’s Payroll Tracker). That doesn’t include a 11-player arbitration class, which MLBTR contributor Matt Swartz projects to cost a combined $28.3MM. Add in a handful of pre-arbitration players to round out the roster, and the Cubs are still shy of $150MM in their projected payroll for next year. Considering that they finished the 2026 campaign just under $250MM in actual cash payroll, there’s a lot of room with which to work. Looking longer-term, the books aren’t too crowded but do have some hefty commitments. Alex Bregman is owed $140MM across the next four seasons, although $55MM of that sum is deferred. Nico Hoerner’s six-year, $141MM extension ($10MM of which is deferred) begins next season. Dansby Swanson still has three years and $78MM on his contract, and likely NL MVP Pete Crow-Armstrong’s six-year, $115MM extension goes into effect in 2027. That quartet gives the Cubs $92.5MM on in guaranteed money already on the 2029 books (albeit with $17.5MM deferred). Adding a $40MM+ salary for Skubal would ramp that up quickly and still leave the Cubs with several holes to fill. Exactly what form the Cubs’ pitching pursuit takes can’t yet be known, but it sounds like a volume-based approach is in order. Sharma writes that names like Michael King and Adrian Morejon could wind up exceeding the team’s comfort level from a pricing standpoint, but whoever they target, the Cubs will be in on grounder- and/or strikeout-heavy pitchers of that profile in order to maximize the team’s dominant infield defense while ideally scaling back on home runs allowed. [Related: 2026-27 Offseason Outlook — Chicago Cubs] Two of the Cubs’ own free agents — Holmes and Peterson — have the top two grounder rates among this year’s class of free agent starters. In the bullpen, lefty Tim Hill and Morejon lead the way, though veterans like Jonathan Loaisiga, JoJo Romero and Ryan Thompson all have ground-ball rates north of 50%. David Bednar, like Morejon, would check both the grounder and strikeout boxes. He’s also expected to be nearly as expensive as Morejon — likely something valued in the range of $15-18MM annually over three to four years. The Cubs typically haven’t been willing to commit multiple years to free agent relievers, though they reportedly made a big bid for Tanner Scott a couple offseasons back and did sign Phil Maton for two years last winter. That Maton contract was the first multi-year deal they’d given to a reliever since Craig Kimbrel in 2019, however. Skubal, 30 later this month, carries a 2.47 ERA, 31.1% strikeout rate, 4.5% walk rate and 44.3% grounder rate across his past 626 1/3 big league innings. He won the American League Cy Young Award in both 2024 and 2025. MLBTR predicted a nine-year, $425MM contract for him last week as part of our annual Top 50 Free Agent rankings.