If the Cubs Are Out on Tarik Skubal, What Do They Do Next?

We're less than three weeks from the (presumed) beginning of a lockout that will plunge the hot stove into an ice bath. Between now and then, the Chicago Cubs have their needs cut out for them. They need to replenish a rotation that's losing five starters from 2026; address the corner outfield due to the free agencies of Seiya Suzuki and Ian Happ; and do more to fix the bullpen. The Cubs have routinely acted more like a mid-market team under Jed Hoyer, staying away from the top tier of free agents since their competitive window opened again. Apparently, the plan is to keep it that way. According to Sahadev Sharma of The Athletic, Chicago doesn't expect to be heavily involved in the bidding for free-agent ace Tarik Skubal.

It feels regrettable that Jed Hoyer isn't doing due diligence by pushing for a meeting with Skubal. However, the Cubs are not a Tarik Skubal away from being a World Series favorite. They are not a Skubal away from dethroning the Brewers. Could the Cubs afford Skubal? If he costs $50 million a year, adding him would push the North Siders' payroll above $250 million for 2027. That's around what it was in 2026, but this would severely restrict their ability to improve other areas of the roster.

Knowing how the front office operates, a Skubal signing would have them filling out the rest of their roster with cheap one-year deals and minor-league pacts. A Cubs team with Skubal would have a rotation of Skubal, a version of Justin Steele that hasn’t pitched in nearly two calendar years, Edward Cabrera, Ben Brown, and some mix of Javier Assad, Braxton Garrett, or some cheap free-agent depth addition. There’s upside there, but no sure thing (outside of Skubal). The bullpen construction would be the same as it has been, making their re-signing of Jacob Webb the “big” move.

As for the outfield, Matt Shaw and his .640 OPS against righties would be the everyday right fielder, and Kevin Alcántara would be the default left fielder. He should get a longer look in the majors, but that's one shaky Plan A. They can hit the trade market to fill these holes, but they moved top organizational prospects Owen Caissie, Jefferson Rojas, and Moisés Ballesteros last season. Jaxon Wiggins’s medicals were enough to scare off the Angels in the failed Reid Detmers deal. That leaves teenager Josiah Hartshorn and catcher Owen Ayers atop a farm system that ranks near the bottom of the league. The point is, the Cubs are in quite a conundrum, and unless they're ready to behave like the Dodgers or Yankees, Skubal might not be the answer. There's too much else that needs to be done. 

So how should the Cubs pivot? For this exercise, let’s assume that not going all-in for Skubal saves them $50 million  They need a starter (ok, two, or even three) and at least one dependable reliever. Outside of Skubal, the other top free-agent starters who have started Game 1 of a postseason series would be Freddy Peralta (30) and Michael King (31). Each hurler is likely to make more than $23 million per year, but no more than $30 million. There's no reason the Cubs shouldn't be all over these guys. A failure to land one of them would signify a loss in confidence in the current roster. There are other playoff-tested, veteran starters who would really help the Cubs’ staff, but these are the only two that can square up against anyone to start the series.

The next-best free-agent starters are Sonny Gray, Nick Martinez, Clay Holmes, and Trevor Rogers. All four of these guys would fit well into the Cubs rotation, but they would each make more sense as the third option, and the Cubs don’t have the depth for that. Gray is 37, Martinez is 36, Holmes will be 34, and Rogers is injury-prone, which is a risk the Cubs can’t afford to take for a while. The interesting caveat here would be if the Cubs pivot to two of the guys from this category, instead of going after King or Peralta. They might be able to sign two of them for a total of $45 million a year. It would have to be Rogers or Gray and Martinez or Holmes, but those combos could still produce a deeper, stronger rotation. Below that group sit Foster Griffin, Casey Mize, Robbie Ray, and old friends Shota Imanaga, Matthew Boyd, and Kevin Gausman. They're viable starters, but again, the Cubs' lack of internal depth means any of them would probably cost more and be asked to do more than befits them if they landed with Chicago.

There’s one more pair of starters here who are interesting fits and would make a great pairing with Peralta or King: Tyler Mahle and Nick Pivetta. After sporting an unsightly 5.13 ERA with the Giants, Mahle turned his season around with the Braves, pitching to a 1.99 ERA in nine starts. He made two playoff starts, allowing only two earned runs in 13 1/3 innings. Peralta or King at the front end, with Mahle rounding out the rotation, would inspire enough confidence.

Pivetta is the more obviously risky pivot option, as he missed four months with a right elbow flexor strain and made only eight starts on the season. Those eight starts were a continuation of his dominance from 2025, wherein he had a 2.87 ERA over 31 starts. In 2026, he had a 2.86 while striking out 42 in 34 2/3 innings. The Padres declined a club option for $14 million due to his injury concerns, but when healthy, he can be the most valuable lottery ticket in this free agency class. The Cubs need to avoid injuries to their rotation, but at the right price, he could fit, too.

The last two guys worth mentioning are the two Asian imports making the jump: Kaima Tara and Hiromi Itoh. Both would surely love the chance to start, but they could also wind up in the bullpen. Tara, who was a dominant closer in 2025, transitioned to the rotation in NPB last season. Walks have been an issue, making a case for his status as a reliever. Itoh is more established as a workhorse, but would be a back-end option—strictly a depth play.

The Cubs need to make a ton of moves to get this pitching staff close to where it needs to be. They'll need to exceed $50 million in 2027 spending to get there. With that being said, it isn’t surprising that Skubal isn’t in their cards. There are just too many holes on this roster to justify giving one guy that much money. The best way they can spend it is to spread what they have around a bit more than that.

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