Jessie is a Bronze Legacy Life Member of the Greater Jacksonville Beaches VFW Post 3270. He served three years in the Active Army as an infantryman (11B) and is currently serving in the U.S. Army Reserves as an I.T. Specialist (25B). He joined the VFW in 2018, having earned his eligibility while deployed in 2012 with the 4-23 Infantry "Tomahawks," 2nd Stryker Brigade Combat Team, 2nd Infantry Division, JBLM (Joint Base Lewis-McChord), Washington in support of Operation Enduring Freedom Kandahar, Afghanistan.

His Reserve service currently includes assignments with the 345th Field Hospital, NAS Jacksonville, Florida; the 1186th DDSB, Jacksonville, Florida; and the 10th BN/108th Regt, Jacksonville, Florida.