🚨 INSIDE WHITE SOX DEBATE: One name keeps quietly surfacing inside White Sox circles, and the growing belief that Roch Cholowsky might be the right fit is starting to turn heads. What makes this potential connection so intriguing goes beyond talent alone, raising questions about timing, direction, and whether Chicago may already be eyeing its next long term answer.

For the first time since 1977, the White Sox have the first overall draft pick in the summer draft, and the timing couldn’t be more favorable.

In a top-heavy draft, Chicago doesn’t have to guess who may fall to them. After wisely picking future Hall-of-Famer Harold Baines in 1977, the Sox are hoping to make another profitable decision. The consensus from scouts and across every major sporting news outlet is that UCLA’s shortstop Roch Cholowsky is the best pick of the coming draft.

But is Cholowsky the best pick for Chicago?

Named Baseball America’s 2025 College Baseball Player of the Year, on paper Cholowsky is the full package. Earning plus grades in four of the five performance categories, with speed being his only deficit, and scoring 65 overall, Cholowsky has much more talent than glove-first shortstop and White Sox 2025 first-rounder Billy Carlson. Cholowsky slashed .353/.480/.710 23 while crushing 23 home runs and drawing 45 walks in 66 games last season, truly showcasing his bat-on-ball ability, power and plate discipline skills. Plus, his added reps as a college player make him a less risky pick than Grady Emerson, a shortstop from Fort Worth Christian High School who is projected to be taken second overall in the draft.

Cholowsky has been compared to Troy Tulowitzki, who was a No. 7 overall pick by the Rockies in 2005. Tulowitzki was also known for his elite defense and power potential at the plate in college as a five-tool player, and his rapid ascent through the minors and strong early career proved that Colorado picked the right guy. Tulowitzki had a modest start to his career and struggled to generate power against big league pitchers, batting .240 and slugging just .292 in 2006. But he made a splash in 2007 while playing nearly the entire season. Tulowitzki’s impressive .291/.359/.479 slash line and 24 home runs earned him the runner-up in NL Rookie of the Year voting. Though ending up no better than a borderline Hall-of-Famer, Tulowitzki did firmly establish himself as a member of the Hall of Very Good — no small feat.

Cholowsky’s comparison to Tulowitzki is a positive sign, and it’s possible that Cholowsky could follow a similar development progression path as Tulowitzki. Cholowsky is a safe gamble for those two reasons alone.

One weakness Sox Machine’s Josh Nelson observed is Cholowsky’s end-of-season struggles, particularly against non-Big Ten pitching. While his underwhelming performance against higher-caliber arms is concerning and could partially be attributed to end-of-season fatigue, having Ryan Fuller as the Sox’s director of hitting should help alleviate those concerns.

Fuller has a proven track record of developing hitters, specifically Adley Rutschman, during his various coaching positions in Baltimore’s minor and major league system. From Rutschman’s drafting to MLB All-Star and Silver Slugger winner, the catcher had Fuller with him as an instrumental guide through the minors and into his first major league years. Fuller’s data-driven approach, emphasis on making smart swing decisions and focus on incremental improvements (as discussed on a MASN Orioles podcast in 2023) have enabled Rutschman to achieve sustainable success. Knowing that Fuller is capable of developing a player with a similar scouting report and grades as Cholowsky’s and translating minor league success to the majors are two more indicators that make drafting Cholowsky ideal.

Between Cholowsky’s raw talent and Chicago’s competent hitting director, the Sox shouldn’t second-guess any leaning toward a selection of Cholowsky. While the Sox should still carefully monitor his junior year and scout other anticipated Top 5 picks, Chicago fans should feel confident in Cholowsky’s fit and future with the South Siders.

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