Captain Bailey joined the Marine Corps through Officer Selection Station (OSS) Amherst, MA in September 2014. He attended Officer Candidates School in June of 2016 and 2017 and was commissioned in May of 2018. Upon commisioning from the University of Massachusetts, Amherst, he reported to The Basic School in July 2018. Upon graduation from The Basic School, he reported to Infantry Officers Course in January of 2019. Upon designation as an Infantry Officer, Captain Bailey was assigned to 2nd Battalion, 5th Marines in Camp Pendleton, CA in April 2019. He served as a Rifle Platoon Commander with Company E. He deployed with the Special Purpose MAGTF-Crisis Response-Central Command from May to November 2020. In December of 2020, Captain Bailey was assigned to the Combined Anti-Armor Team One within Weapons Company. He deployed with the 31st Marine Expeditionary Unit from May to November 2022. Upon completion of his active duty service, Captain Bailey affiliated with Company A, 1st Battalion, 25th Marines in Brunswick, ME as a Rifle Platoon Commander and Executive Officer. Captain Bailey assumed command of Company A on June 23, 2025.
He graduated from the University of Massachusetts, Amherst with a Bachelor of Science in Sociology. When not fulfilling his duties with the Reserves, he is working for a construction company and working towards joining the Boston Fire Department.
First Lieutenant Bailey’s personal decorations include the Navy and Marine Corps Achievement Medal, Inherent Resolve Campaign Medal, and Sea Service Medal with gold star in lieu of second award.