was born in Welch, WV. He is a graduate of Flagler Palm Coast High School. Mr. Bailey proudly served in the United States Army 10th Mountain Division. Upon completion of his enlistment with the United States Army, he went on to receive his Bachelor of Business Administration and Masters of Accountancy from Stetson University. Mr. Bailey has spent majority of his career in the Insurance and Payroll Industries before joining the Sheriffs Office.

Mr. Bailey has served on the board of the Boys and Girls Clubs, as well as Treasurer of the Leesburg Rotary. He has three sons; Logan, Drew, and Elijah. Currently resides in Leesburg, FL.