LT Bailey is from Youngstown, OH. After graduating high school, he attended The Citadel where he earned a Bachelor of Science in Civil and Environmental Engineering. After graduation, LT Bailey earned his commission through ROTC in 2017 and reported to NAS Pensacola to complete flight training. He completed his primary training with VT-10 at NAS Pensacola and advanced training with VT-4 at NAS Pensacola, ultimately earning his Wings of Gold in April of 2018. LT Bailey reported to VP-5 in December of 2019 where he assumed the duty of CSM. In January, he went to MAJIC (Multi-TDL Advanced Joint Interoperability Course) school. LT Bailey led Combat Aircrew 2 through the entirety of VP-5’s 2022 7th fleet deployment as the Mission Commander. LT Bailey was designated as an Instructor TACCO and Instructor TO while at VP-5. LT Bailey checked into Operational Test and Evaluation Force in May 2023 and received his DAWIA 1 Certification in July 2024. In February of 2025, LT Bailey reported to the USS Gerald Ford (CVN-78) to assume the roles and responsibilities of a catapult and arresting gear officer (shooter). His personal decorations includes Navy Commendation Medal and a Navy and Marine Corps Achievement Medal.