Cholowsky attended
Hamilton High School in
Chandler, Arizona, where he played on the
baseball team as a shortstop and pitcher and on the
football team as a quarterback. As a junior in 2022, he hit .315 with two home runs. As a senior in 2023, he batted .466 with 11 home runs and 35 RBI and was named the Gatorade Arizona Baseball Player of the Year. He was considered a top prospect for the
2023 Major League Baseball draft, but went unselected and enrolled at
UCLA to play
college baseball. As a freshman at UCLA in 2024, Cholowsky played in 52 games and hit .308 with eight home runs and 33 RBI. After the season, he played in the
Cape Cod Baseball League with the
Orleans Firebirds. As a sophomore in 2025, Cholowsky was named the
Big Ten Conference Baseball Player of the Year, Big Ten Conference Defensive Player of the Year, and helped lead UCLA to their first
College World Series in 12 years. He also was awarded the
Brooks Wallace Award, given annually to the nation's best college shortstop. Cholowsky finished the season with a .353 batting average, 23 home runs, and 74 RBI over 66 games and earned first team
All-American honors from Baseball America. After the season, he was named to the
United States national baseball team. ==References==