Major Benjamin Gentry is a native of Roanoke, Virginia. He enrolled in the United States Naval Academy in 2008 and graduated with a Bachelor's of Science in International Relations, a Minor in Japanese Language, and a commission as a Second Lieutenant in US Marine Corps in 2012. Maj Gentry attended and graduated The Basic School in Quantico, VA in 2013, and served as a Training Officer with Bravo Battery, 1/11 in Camp Pendleton, CA. In 2015, as a First Lieutenant, he attended the Basic Officer Leader Course - Field Artillery at Fort Sill, Oklahoma, and returned to 1st Battalion, 11th Marines serve as a Platoon Commander and Fire Direction Officer for Battery A.
In summer of 2015, Maj Gentry served as Expeditionary Fire Support System Platoon Commander, Battery A, 1st Battalion, 11th Marine Regiment. He deployed on the 11th Marine Expeditionary Unit (MEU) from 2016-2017 and participated in MEU operations and exercises in Oman, Sri Lanka, and Djibuti, where he was promoted to the rank of Captain. Upon return from deployment, Maj Gentry was assigned to Advisor Training Branch of I Marine Expeditionary Force - Expeditionary Operations Training Group. There, he served as the Assistant Operations Officer and coordinated the design, execution, and evaluation of pre-deployment training pipelines, certification, and field re-evaluation programs for Task Forces Al-Assad and Al-Taqqadum, as well as the Georgia Deployment Program.
In 2018, Maj Gentry reported to the 31st MEU in Okinawa, Japan to serve as the Targeting Information Officer and Assistant Fire Support Officer. He attended Joint Targeting School in Dam Neck, Virginia, and deployed at sea with the 31st MEU during three iterations and supported a fourth from shore in primary and numerous auxiliary capacities with service during multiple exercises in Australia, the Philippines, and Japan.
In 2020, Maj Gentry reported to 2nd Battalion, 10th Marines, where he served as Assistant Operations Officer and Headquarters Battery Commanding Officer during Infantry Training Exercise (ITX) in 29 Palms, California. He completed Expeditionary Warfare School in 2021. Following ITX, he served as the Regimental Assistant Fire Support Coordinator, and subsequently as the Regimental Assistant Operations Officer. He left active duty to the Individual Ready Reserve in 2023, and was promoted to the rank of Major from the IRR in September 2024.
While in the IRR, Maj Gentry obtained state and national EMT and Paramedic licenses, and served the community as a volunteer firefighter and EMT in Onslow County, NC, and as a full-time basic EMT and EMT-Paramedic in Pender County, NC.
In December of 2025, Maj Gentry entered the IRR and reported to 2nd Battalion, 14th Marines in January to serve as Battalion HIMARS Planner. In March of 2025, he took command of Battery F, 2/14.
Maj Gentry's awards include the Navy and Marine Achievement Medal, and various service and campaign medals.