Private (Pvt) Jason A. Caldwell enlisted in July of 2002 and then completed boot camp at Marine Corps Recruit Depot (MCRD) Parris Island on March 24, 2003. Pvt Caldwell completed Marine Combat Training (MCT) in April of 2003. Upon completion of Logistics Vehicle System Operator Course and obtaining the MOS of 3533, from 2003 - 2005, LCPL Caldwell served as the Logistics Vehicle System Operator with Marine Wing Support Squadron (MWSS-471) Reserve Unit located in Johnstown, PA . In February of 2006, Lance Corporal Caldwell was promoted to the rank of Corporal (Cpl) being stationed in Okinawa Japan and assigned with 9th Engineer Support Battalion.
From 2006 to 2009 assigned to 9th Engineer Support Battalion, Sergeant Caldwell deployed twice to Iraq in support of Operation Iraqi Freedom and Operation Enduring Freedom while serving as the Wrecker Operator in support of all vehicle recovery in the area of operations.
In April 0f 2009, Sgt Caldwell received orders to Recruiters School upon his return from Iraq. Upon completion and graduation, he was later assigned to Recruiting Station Springfield, Recruiting Sub Station Auburn as a canvassing recruiter, where he was meritoriously promoted to the rank of Staff Sergeant (SSgt) in Jan 2011.
Upon a successful tour and completion on recruiting duty, SSgt Caldwell received orders to III MEF, G4 as the MAGTF Movement Control Coordinator where he served in the billet until June 2014. SSgt Caldwell volunteered to return back to recruiting duty after spending two years in the fleet.
In 2016, SSgt Caldwell was meritoriously promoted to the rank of Gunnery Sergeant (GySgt), while serving as the Station Commander for Recruiting Sub Station Bridgeport, CT. From 2016 to 2018, GySgt Caldwell served as the Station Commander for Recruiting Station Hartford, CT. He later received orders as the Officer Selection Assistant and moved to Providence, RI and served in the billet from June 2018 to June 2020. From June 2020 to June 2022, MSgt Caldwell served as the Assistant Recruiting Instructor for Recruiting Station Springfield. In June of 2022, MSgt Caldwell executed orders to serve as the Officer Procurement Course Head on the National Training Team, MCRC G3. In July of 2024, MSgt Caldwell received orders to Recruiting Station Boston, HQ and served as the Assistant Recruiting Instructor until June 2025. MSgt Caldwell is currently assigned to Recruiting Station Albany and serving as the Recruiting Instructor.
MSgt Caldwell and his wife Frances have been married since July of 2009. Together, they have two children: daughter Xandria (21) and son Jason Jr. (14).