As Chicago’s young core takes shape, a breakout season from outfielder George Wolkow could address a massive White Sox need.
There’s so much to be excited about right now for Chicago White Sox fans. That’s true for both the major league club and the organization’s farm system.
The White Sox developed a promising young core in 2025. That growth not only led to a more enjoyable second half of baseball on the field, but also pointed toward a brighter future ahead.
And the prospects below the big league level have started their professional careers strong.
Shortstops Caleb Bonemer and Billy Carlson are both top-100 prospects in baseball. Infielder Sam Antonacci is another fast riser who could find himself in the big leagues as soon as 2026.
Chicago also has a wealth of young pitching and holds the No. 1 overall pick in the 2026 MLB Draft, giving the organization an opportunity to select a premium talent — likely UCLA shortstop Roch Cholowsky.
But something is still missing. Of all the players mentioned above, none are natural outfielders.
The White Sox do have Braden Montgomery, the current No. 1 prospect in the organization, projected to make his debut in 2026 in a corner outfield role. Montgomery appears to be the right fielder of the future. Beyond him, however, the organization lacks meaningful outfield depth.
That concern is amplified by the fact that both Luis Robert Jr. and Andrew Benintendi are nearing the end of their contracts with the White Sox.
That’s exactly why one prospect has the potential to change everything — the chance to give Chicago another future star with a game-changing skillset.
That prospect is outfielder George Wolkow, a high-upside draft pick selected in the 7th round out of Downers Grove North High School in the Chicagoland suburb of Downers Grove, IL.
Wolkow remains a high-ceiling prospect today, recently being named by MLB Pipeline as the prospect set to have a breakout 2026 campaign."
“Few players in the Minors have as big of a difference between their ceiling and floor as Wolkow,” MLB.com writes. “The 6-foot-7 slugger has near-top-of-the-line raw power but hasn't yet been able to tap into it because of swing-and-miss and chase issues. The good news is he cut his K rate from an untenable 40.3 percent in 2024 to a still-high 29.6 percent in 2025. Further improvement, especially against breaking balls, could enable him to reach that long-awaited breakout.”
It has been easy for White Sox fans to forget about Wolkow amid all the excitement surrounding the team.
In 2025, he hit 13 home runs and stole 33 bases. While he continued to draw walks, the 147 strikeouts were a blemish on his season, and a .223 batting average in Low-A is difficult to ignore.
Still, across 761 career at-bats in Kannapolis, Wolkow has produced 34 doubles, 26 home runs, 115 RBIs, and 42 stolen bases.
The upside is clear. And sometimes it’s easy to forget that he’s still only 19 years old. Wolkow will turn 20 before Opening Day, but he has ample time to develop in the areas that matter most.
If he continues to cut down on swing-and-miss and improves his ability to handle breaking balls, more consistent contact could allow his natural power to fully emerge.
The result could be a 6-foot-7, left-handed outfielder capable of hitting 25 home runs while stealing 30 or more bases in a season. That kind of production would earn him a promotion, elevate him into Top 100 prospect territory, and give the White Sox another cornerstone piece in the outfield.
That could change the entire outlook of the rebuild.