Leo wrestled at Billerica Memorial High School under Coach Robert Bellanger where he finished with a career record of 154-30. He was a two-time State and All-State Champion, a 2013 New England Champion and a two-time All American. Leo was an All-Conference wrestler in both wrestling and soccer and was a captain of the wrestling team. Leo is currently majoring in criminology and wrestling in Division I at West Virginia University, where he finished 4th in the Big 12 Championships in his freshman season.