CDR Leonard grew up in Holliston, MA, and graduated from the University of Tennessee in 1995. He was commissioned through Officer Candidate School in 1997 and earned his wings in 1998. As a Naval Aviator, he has amassed over 2,200 hours and was designated a SH-60B Weapons and Tactics Instructor. He graduated from the United States Naval War College with a Master's Degree in National Security and Strategic Studies (with highest distinction) in 2011, and earned a Master's in Business Administration from Creighton University in 2017. CDR Leonard is married and has two children.