Cleary grew up in Owings, Md. where he was a three-sport student-athlete at Northern High School, playing football, basketball and lacrosse. He graduated in 2011.
He went on to attend Salisbury University and was a member of the Seagulls' men's lacrosse team (2013-2015) as a defensive midfielder. During his collegiate career, he was a member of two CAC championship teams, along with the 2014 national finalist team. Cleary helped coach the Salisbury lacrosse camp along with the Crown Youth Lacrosse Clinics. He graduated with a degree in physical education.
After leaving Salisbury, Cleary became a physical education and health teacher at Havre de Grace High School in Harford County. He also served as the Warriors' girls basketball coach, an assistant to the lacrosse team, primarily working with the defense, and is currently an assistant with the football team as the safety's and receiver's coach.
He currently resides in Fells Point, Baltimore, Md.