For the second time in just over a week, the White Sox have watched a player slip through waivers and land with their neighbors to the north. This time, it’s infielder Ben Cowles, who’s headed back to the Cubs after a brief stint on the South Side.
The move comes not long after the Cubs plucked left-hander Ryan Rolison from the White Sox, continuing a quiet but notable back-and-forth between the two Chicago clubs. Cowles, 25, was originally a Yankees draft pick back in 2021 and worked his way through their system before being dealt to the Cubs at the 2024 trade deadline in the Mark Leiter Jr. deal.
Cowles is the kind of player who’s always had intriguing tools but hasn’t quite put it all together. His time in the Yankees’ system was marked by flashes of offensive upside-solid on-base skills, some pop-but consistent playing time was hard to come by due to a string of injuries.
When he finally did stay on the field in 2025, logging a career-high 128 games, his production dipped. His on-base percentage, usually hovering in the .350-.370 range, fell to .300.
His OPS dropped significantly as well, from .829 in 2024 to just .671 last season.
After the Cubs designated him for assignment, the White Sox claimed him in September and gave him a short look in Triple-A Charlotte. The results weren’t eye-popping-just a .565 OPS in 15 games-but the Sox clearly saw enough to give him a shot.
That opportunity didn’t last long. Chicago’s recent waiver claim of catcher Drew Romo forced a roster crunch, and Cowles was the odd man out.
Now, he’s back with the Cubs, this time as infield depth on their 40-man roster. It’s a low-risk move for the North Siders, who know Cowles well and can afford to see if he can rediscover the promise he showed earlier in his career.
As for the White Sox, this move doesn’t shake up their infield picture much. Cowles was always a long shot to crack the big-league roster, especially with players like Munetaka Murakami, Chase Meidroth, Colson Montgomery, Lenyn Sosa, and Miguel Vargas all in line for meaningful reps in 2026. Short of a rash of injuries, Cowles wasn’t going to see much action at Guaranteed Rate Field.
But even as they lose a depth piece, the Sox are in a better spot than they were a year ago. The 2025 roster featured names like Jake Amaya, Vinny Capra, and Will Robertson-solid players, but not the kind that move the needle.
Now, with Colson Montgomery ready to take on a major role and Jarred Kelenic adding juice to the lineup, there’s a new energy around this team. It’s not a finished product, and no one’s penciling them into October just yet, but the arrow is pointing up.
The White Sox might still take their lumps in 2026, but there’s a foundation forming. The front office is making moves with a purpose, and fans have more reason than ever to keep an eye on how this group evolves. Losing Cowles won’t derail that progress-it’s just part of the roster churn that comes with building something sustainable.