Leonard was born and raised in Chicago , Illinois .  He received his Bachelor of Arts, majoring in Speech Communication, from the University of Illinois at Urbana-Champaign. He also obtained his Juris Doctorate and Masters of Business Administration from the University of Illinois . While attending Illinois, Leonard was a mentor to “at risk youth,” a Graduate Student Representative for Student Government, a member of the Social and Finance Committees of the Black Law Student Association, a member of the T.J. Reddick Bar Association, a speaker against sexual assault, and a Guardian Ad Litem. He is a former Assistant Attorney General for the State of Florida , where he established, modified, and enforced child support. Leonard is also a former insurance defense attorney.  He is a past Treasurer and Secretary of the Government Lawyer Association of the Florida Bar.

Leonard is admitted to practice before all Florida state courts and the United States Supreme Court.