Leonard attended Miami Killian High School, where he holds records in football and track and field.

He was named a first-team All-Conference USA selection at cornerback and punt returner.

Leonard was not selected in the 2016 NFL draft and signed a contract as an undrafted free agent with the Houston Texans on May 5, 2016.

Leonard would go on to have an impressive rookie season with the Tiger Cats, recording 72 tackles, 7 interceptions and returned a blocked field goal for a touchdown in his first game against the Toronto Argonauts.

[5] Leonard has a cousin, Jeremiah McKinnon, who currently plays cornerback for the New York Giants.