Cunningham attended
Lady Bird Johnson High School in
San Antonio, Texas. As a junior in 2024, he was named the
San Antonio Express-News Player of the Year after hitting .437 with 36 stolen bases. He was also named the 2024
USA Baseball Player of the Year. During the summer of 2024, he played for the
United States national under-18 baseball team. He was named the MVP of the World Cup Americas Qualifier after hitting .417 with 12 RBI. In August 2024, Cunningham played in the High School All-American Game at
Petco Park. He committed to play
college baseball at the
University of Texas. Entering his senior year in 2025, Cunningham was considered a top prospect for the upcoming MLB draft. As a senior in 2025, he hit .509 with 23 extra-base hits and 21 stolen bases and was named the Gatorade Texas Baseball Player of the Year. ==Professional career==