Cover photo for Garland Woolfolk's Obituary
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1972 Garland 2022

Garland Woolfolk

July 19, 1972 — June 30, 2022

Garland “Jon” Woolfolk, loving husband and overall great American, passed away unexpectedly on Thursday, June 30, 2022, at his home on Fort Meade, MD, at the age of 49.

Jon was born in Owensboro, KY on July 19, 1972 to William Woolfolk and Lena Chambers.  Jon, a loyal friend and tenacious defender of the weak, was a career United States Army leader retiring in 2010 at the rank of Major before transitioning to a career as a Department of Army Civilian and then becoming a DoD Civil Servant with Defense Counterintelligence and Security Agency (DCSA).

Jon enlisted in the Army in 1990 as a Military Police Officer, became a Master Rated Jumpmaster, and eventually was assigned to the Commanding General and Division Command Sergeant Major’s Command Group of the 82d Airborne Division in Ft. Bragg, NC.  After serving in the Army for eight years, Jon attended Officer Candidate School, received his commission in 1999 as an Infantry Officer, and earned the coveted Ranger Tab. During Jon’s combat deployments to Iraq, he served as company commander for B Company 1-505, Parachute Infantry Regiment, 82nd Airborne Division. His command in Iraq included severe duty in Fallujah.  Jon served in many units and roles throughout his military career, starting with the 6th Infantry Division; the 82nd Airborne Division, where he also commanded the Division Headquarters Company; and First United States Army, achieving the rank of Major and retiring in November 2010.  Jon continued his service as a civil servant on Fort Bragg, Bagram Airfield, Afghanistan, Fort Meade, and eventually in the White House, as he became the Senior Advisor to the National Security Advisor to the Vice President of the United States.  At the time of his passing, Jon was excelling as a DoD Civil Servant with DCSA.  Jon was a rising star within DCSA’s National Background Investigation System Planning and Deployment Office, helping to shape and operationalize Personnel Vetting end-to-end transformations to achieve Trusted Workforce 2.0.

Jon loved spending time with his darling wife, Liesa, and was a huge movie buff.  He enjoyed the Marvel Cinematic Universe as well as action, science fiction, and drama. Jon enjoyed reading, discovering independent music artists, and his “nerd” shows and games; he had a particular fondness for Warhammer 40,000. Quick with a joke, an impression, or a quote from a movie or TV show, particularly a British comedy like “Blackadder” or “Fawlty Towers,” Jon could bring a smile to anyone’s face.

Jon leaves behind his wife, Liesa Jacobs-Woolfolk; two daughters, Bianca Rodriguez (Armando) and Julia Hall; a brother, William Woolfolk (Kathleen); stepfather, David Chambers; stepmother, Cynthia Woolfolk; father-in-law, Charles Jacobs; two granddaughters; a nephew; and nieces. He is preceded in death by his father and mother.

A public military honor service will be announced at a later date. In lieu of flowers, Liesa respectfully asks that we honor Jon’s giving spirit with a donation to Headstrong, (, which provides confidential, barrier-free and stigma-free evidence-based trauma-focused treatment for the military community.   If you would like to reach out to the family that a donation has been made in Jon's memory, please feel free to use the following email:

To order memorial trees or send flowers to the family in memory of Garland Woolfolk, please visit our flower store.


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