Cunningham was born in Clinton, Maryland, to Searcy Blankenship and Ron Cunningham. His older sister Davalyn played in the WNBA.\n', '

Cunningham began his prep career at St. John\'s College High School in Washington, D.C. While a junior, he averaged 10 points per game and 7.4 rebounds. One of his teammates, Dwayne Anderson, would later play at Villanova with Cunningham.\n', '

As a senior, Cunningham transferred to Potomac High School, which he led to a 27–0 season under Head Coach Rico Reed. He averaged 13 rebounds, 20 points, and four blocked shots per game at Potomac. He was honored as the Washington Post Metropolitan Player of the Year.\n', '

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