Cubs Free-Agent Starting Pitching Target: Trevor Rogers

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Tarik Skubal will be the hotness, for however long his free agency lasts. Wherever he eventually signs, he'll break the record for total guaranteed dollars and annual average value for a starting pitcher, because he brings all the things teams look for in their aces. His raw stuff is at the top of the scale. So are his results. Skubal is even more durable than most modern starters, although he did finally miss some time in 2026. He's the complete package.

The Chicago Cubs, of course, don't typically pay for the complete package. Complete packages are wildly expensive, and sometimes, they turn out to be defective or unduly fragile, even though they weren't advertised as such. Better to shop on Temu. If you buy the high-end stuff there, it'll still be a knockoff, but it might be a high-quality knockoff, and you'll have more to spend on a second thing from Temu, or on fast-casual dining (instead of a steakhouse), or on a middle-shelf shot of whiskey. It's not a popular approach, and it's not clear whether it's the right one, but the smart money is always on Jed Hoyer spending smart money, rather than big money.

This winter, Skubal won't be the smart money option. It'll be Trevor Rogers, the Orioles southpaw who hits free agency with far fewer bona fides and no chance of cracking $200 million in earnings (let alone $300 million), but who's also a year younger than Skubal—and maybe not as much worse as he looks, at first glance.

Why Trevor Rogers is the Stealth Ace of This Winter's Class

Rogers hits free agency after pitching for the Orioles for parts of the last three seasons, but he entered pro baseball as a first-round pick by the Miami Marlins, in 2017. With the Fish, he became a top prospect, prized for the deceptiveness of his low-slot delivery and the way his fastball seems to jump on hitters. Injuries and other health problems have always been his bugaboo. Since reaching the majors in 2020, he's dealt with COVID (the actual illness, not just the logistical nightmares); back trouble; a lat strain; a biceps strain; a hyperextended knee; and, in 2026, a severe case of the flu that knocked him out of the rotation for three weeks and left him weakened for his first few starts even after returning.

When he's been on the mound, however, Rogers has flashed some marvelous things. In 2025, once he returned from a prolonged absence due to that knee injury, he mowed down opponents ruthlessly, with a 1.81 ERA and a 24.6% strikeout rate in 18 starts. After a rocky start in 2026 (and that prolonged period of struggle as he regained weight and strength throughout the late spring), he posted a 2.90 ERA in 20 starts beginning June 1, averaging more than six innings per outing.

Always a nightmarish at-bat for fellow lefties, Rogers succeeds or fails based on his ability to get out opposite-handed batters. On that score, there's some bad news: his changeup took heavy damage in 2026. Opponents hit .336 against it. However, the pitch has a good movement profile, tumbling nicely off the plane of his flat, running four-seamer, and it reliably induces ground balls. Meanwhile, Rogers can miss bats with his fastball, which is more essential than ever in the age of ABS, and he's showing growing facility with his sinker, cutter and sweeper, with the former two forcing some weak contact and the latter racking up whiffs in left-on-left matchups.

How Joining the Cubs Could Take Rogers's Game to the Next Level

The best way for a Cubs fan to conceptualize Rogers might be as a better version of Matthew Boyd. The younger lefty has just a bit more funk on his fastball, but he also has better control than Boyd—or almost anyone, for that matter. Rogers walked 6.9% of opposing batters in 2025, and that figure fell to 5.6% in 2026. Focus on those 20 starts in which he was fit and firing, and it falls all the way to 4.4%. That he can fill up the zone that way without giving up home runs at an alarming rate sets him apart from Boyd and Shota Imanaga, and it makes clear why he'll be in high demand this offseason, even after the Orioles attached draft-pick compensation to him by extending the qualifying offer to him at the beginning of the month.

As good as his numbers looked, though, Rogers could have been even better—and might be, with a defense as good as the Cubs' behind him. According to Statcast, a leaky Orioles defense directly cost Rogers 6 runs last season. In a lighter workload (520 batters faced, compared to Rogers's 699), Boyd got an 8-run boost from working in front of the Cubs' defenders, who won the Team Fielding Bible Award for the second year in a row.

Rogers isn't as defense-dependent as Boyd and his ilk, because he strikes out more batters than they do. Put him in front of an elite team defense for a full season, though, and Rogers might well be a Cy Young Award contender. Indeed, he was one (in a down-ballot way) even in 2025, when he didn't pitch enough innings to make a serious push for the award and only had a fair-to-middling Baltimore defense behind him.

The Price Tag on a Trevor Rogers Deal

Because the Cubs spent past the first competitive-balance tax threshold in 2026, signing any free agent with a qualifying offer attached to them comes at a relatively heavy cost. Chicago would give up its second- and fifth-highest picks in the 2027 MLB Draft in the process of signing Rogers and lose some spending power in the all-important international free agent market. The hurler is also likely to command a four- or five-year deal worth somewhere north of $23 million per year. That's a hefty investment. Comparing Rogers to Joe Musgrove (who signed a five-year deal with his hometown Padres for $100 million that began in 2023) from 2022 illustrates that the price tag includes a premium based on the rarity of frontline lefty starters being available in free agency, even if they're relatively unaccomplished.

In this case, though, it might make sense to roll the dice. The injuries that have made Rogers's progress toward stardom so start-stop haven't been major arm maladies. He's young enough to be viable even at the end of a six-year deal, if adding that would get a deal over the line and spare the team something in the annual average value department. Few pitchers on this (or any) market offer the ability to rack up strikeouts, minimize walks and keep the ball in the park; Rogers checks all those boxes. The slew of hurlers available without draft picks attached to them make spending that capital on this guy a big bet, but Rogers's profile suits the Cubs nicely. They can make him better, and he would do the same for them. He might be Temu Tarik Skubal, but when you put it that way, isn't he a bargain?