A native of Anniston, Alabama, Master Chief Leonard enlisted in the United States Navy in September 1993. He reported to basic training in Great Lakes, Illinois September 7, 1993. He graduated from Apprentice Training Division as an undesignated seaman and reported to his first command, January 1993 USS Puget Sound (AD 38) Norfolk, Virginia.
He reported to USS Whidbey Island (LSD 41) Little Creek, Virginia in October 1995 and was advanced to Petty Officer Third Class. In October 1997, he reported to Commander, Fleet Activities, Yokosuka, Japan, and was advanced to Second Class Petty Officer. In November 1999, he reported to Nuclear Propulsion Training Unit, Charleston, South Carolina and was assigned as the Leading Petty Officer of the Postal mailroom.
In November 2002, Master Chief Leonard reported to National Support Element, Larissa, Greece and advanced to Petty Officer First Class and was named Sailor of the Year for 2004. He then converted to Navy Counselor, and in December 2005, reported to USS Vicksburg (CG 69) Mayport, Florida as the ship’s Career Counselor. In January 2007, he reported to USS Doyle (FFG 39) Mayport, Florida. While assigned to Doyle, he earned his Officer of the Deck-Underway designation, selected as Sailor of the Year 2007, and advanced to Chief Petty Officer in 2008.
In January 2009, he reported to Naval Air Station (NAS) Jacksonville as the installation Career Counselor encompassing 110 tenant commands. In February 2011, he reported to USS Frank Cable (AS 40) Agana, Guam.
He was selected for the Command Senior Chief program in February 2012 and selected for Master Chief in 2014.
He served as Command Master Chief at Naval Technical Training Center Meridian, Mississippi from April 2013 to April 2015. Master Chief Leonard assumed duties as Command Master Chief of USS Vicksburg (CG 69) April 2015-July 2016 where he successfully led her into a homeport shift and entered her into CG Modernization. He assumed duties as Unmanned Patrol Squadron ONE NINE (VUP-19) as the first Command Master Chief August 2016- September 2018.
He currently serves as Naval Air Station Whiting Field Command Master Chief, assuming duties October 2018.
His personal awards include the Meritorious Service Medal, Navy Marine Corps Commendation Medal, Navy Marine Corps Achievement Medal , Navy Good Conduct , the Military Outstanding Volunteer Service Medal, and numerous other campaign and service awards.