A native of Edgewater, New Jersey, Robert "Rob” Bailey enlisted in the United States Navy in October 1996 in Brooklyn, New York. He attended Recruit Training Command in Great Lakes, Illinois, and Engineman "A” School at Naval Training Center Great Lakes, graduating in 1997.

His subsequent duty station was aboard the aircraft carrier USS Abraham Lincoln, CVN-72, homeported in Everett, Washington, from 1997 to 2000. While serving in the nuclear reactor department, he trained as a collateral duty Master-at-Arms and completed his tour assigned to the ship's Security Force. In 1998, the Abraham Lincoln deployed to the Persian Gulf in support of Operation Southern Watch, earning the Armed Forces Expeditionary Medal and the Meritorious Unit Commendation.

Rob joined the Veterans of Foreign Wars Montgomery Memorial Post 7452 in 2013, where he is a Gold Legacy Life Member. He served as the Post Commander from 2016-2022. Rob is a five-time All-State Post Commander and earned the distinction of being an All-American Post Commander in 2020. Rob served in various positions at the District level, including District Commander. He served as the State Inspector in 2022-2023 and as the State Chief of Staff in 2023-2024.

Rob is a Life Member of the Combat Veterans Motorcycle Association 24-2, serving as the Chapter Treasurer since 2019. He is a member of Yorkville American Legion Post 489, The Naval Order of the United States, and a Life Member of AmVets Post 103. He is a Charter Member of Pvt Henry M Hardenbergh, Camp No. 39, Sons of Union Veterans of the Civil War, where he served as the Camp Secretary. He previously served as Treasurer for the Kane County Veterans Assistance Commission Executive Board and as Public Relations Officer for Save A Joe, Inc. Veterans Charities.

Rob is currently retired and resides in Oswego, Illinois, where he lives with his fiancé and children.