Oliver Dunn Signs with White Sox, Looking for a Fresh Start After Tumultuous Milwaukee Stint

Two years ago, Oliver Dunn was one of the more intriguing under-the-radar prospects in the game. After earning Breakout Player of the Year honors in the 2023 Arizona Fall League, the infielder was traded from the Phillies to the Brewers in exchange for prospects Hendry Mendez and Robert Moore. At the time, it looked like a savvy move by Milwaukee – a bet on a versatile, athletic player with a strong glove, sneaky speed, and a quick bat.

Fast forward to the end of 2025, and Dunn’s journey has taken another turn. The now-28-year-old has signed a minor league deal with the Chicago White Sox, aiming to reboot a career that hasn’t quite gone according to plan.

A Promising Start That Never Fully Materialized

When the Brewers acquired Dunn, he hadn’t even played a game at Triple-A. Still, there was buzz that he could compete for the team’s third base job heading into 2024. That excitement wasn’t unfounded – Dunn brought defensive versatility, above-average athleticism, and the kind of bat speed that suggested untapped offensive potential.

Milwaukee gave him the nod out of Spring Training, handing him the Opening Day third base job in 2024. But the adjustment to major league pitching proved steep.

In 41 games, Dunn hit just .221 with a .282 on-base percentage and a .316 slugging mark. The real red flag, though, was the 38.5% strikeout rate – a number that made it hard to keep penciling him into the lineup.

Shortly after being optioned to Triple-A, Dunn suffered a season-ending back injury. Just like that, a promising opportunity was derailed.

2025: A Second Chance, but Similar Struggles

Dunn came into Spring Training in 2025 looking to re-establish himself, and once again earned a spot on the Brewers’ Opening Day roster. But this time, his stay in the big leagues was even shorter.

Despite a fun moment – a squeeze bunt executed with the then-viral “torpedo bat” – Dunn couldn’t find his rhythm at the plate. Through 17 games, he slashed .167/.205/.222.

While his strikeout rate ticked down slightly, it wasn’t enough to offset the lack of offensive production. With two minor league options still in his pocket and a need for more consistent at-bats, the Brewers sent him back to Triple-A.

That’s where he spent the bulk of the 2025 season, finally getting his first extended taste of Triple-A ball – the level he had skipped entirely on his way up. After a slow start with the Nashville Sounds, Dunn showed some signs of life as the season wore on. But overall, the numbers still didn’t jump off the page: a .208/.315/.338 slash line in Triple-A wasn’t enough to force the Brewers’ hand, especially with Caleb Durbin emerging as a legitimate option at third base.

New Chapter in Chicago

Now, Dunn is headed to the South Side of Chicago, where he’ll join the White Sox on a minor league deal for the 2026 season. It’s a low-risk move for a team that’s in the midst of a rebuild and looking for any kind of spark – but it’s also not a guaranteed ticket back to the majors.

The White Sox have a crowded infield picture heading into 2026. Young players like Lenyn Sosa, Chase Meidroth, Colson Montgomery, and Miguel Vargas are all expected to be in the mix for regular playing time. That means Dunn will likely have to earn his way back through a strong Spring Training or by producing in Triple-A.

There’s still a path back to the majors for Dunn – it just won’t be an easy one. He’ll need to recapture the form that made him a standout in the Arizona Fall League and show that he can adjust to big league pitching.

The tools are still there. The question is whether he can put them all together consistently enough to make an impact.

What Could Have Been in Milwaukee?

As Dunn closes the book on his time in Milwaukee, there’s a lingering sense of “what if?” What if the Brewers had let him get his reps in Triple-A before throwing him into the deep end?

What if the back injury hadn’t cut his rookie campaign short?

Development isn’t always linear, and Dunn’s path has been anything but smooth.

Still, he’s just 28, and the White Sox are giving him a chance – which is all a player like Dunn needs. A fresh start, a clean slate, and maybe, just maybe, a shot at rewriting his story.