Cubs Might Have Gotten a Real Steal from White Sox

Back in December the White Sox picked up left-handed pitcher Ryan Rolison, claiming the former first round pick off waivers from the Colorado Rockies. The 28-year-old made his MLB debut last season and despite the rocky results there are some signs that Rolison could be a real steal for the Cubs, who grabbed him off the White Sox’s 40-man roster.

The Cubs have plenty of pitching depth heading into the 2026 season and with that advantage the front office is able to take a chance on a few additional arms to see if one of them pops off in their organization. Rolison has an option year remaining, which can give the left-hander an edge over some of the other pitchers the Cubs have signed on minor league deals this offseason. If the lefty looks good at Triple-A, then he’ll be one of the guys near the top of the depth chart that can be easily shuttled between Iowa and Chicago.

No matter how you break down his first stint in the big leagues the numbers were bad for Rolison. He made 31 appearances with the Rockies and posted a 7.02 ERA in 42.1 innings. The left-hander only recorded a 13% strikeout rate, while walking 10.4% of the batters he faced. Opponents also crushed Rolison to the tune of a .318 batting average.

Rolison features a fastball that averages 93mph, while mixing in a curve ball, slider and the occasional change up. So, what exactly did the White Sox and now the Cubs see in Roslin to put in a waiver claim on him? Well, he did a pretty good job during his time at Triple-A in the Rockies system in 2025, as Roslin had a 3.34 ERA in 29.2 innings, with a 25.2 K%.

That’s all nice and good for gaining confidence in the minor leagues, but as we saw that didn’t translate in Colorado. So, why should any Cubs fan care about Rolison and his potential? Well, the Cubs do have a good track record of restoring pitchers who have been searching for answers and while that individual still has to put in the work and buy in to new methods, Rolison’s pure stuff on the mound compares quite favorably to a current Cubs success story.

Rolison and Justin Steele share several characteristics, including Steele’s unique fastball.

That’s certainly a starting point for the Cubs and Rolison to get in the lab and figure out how to raise his level in the big leagues. If the left-handed pitcher can get back on track, then the Cubs could definitely keep him around beyond 2026. Rolison is arb eligible in 2027, and could be under team control through the 2029 season.