Bailey was born in Anchorage, Alaska, and has been kicking a soccer ball for as long as he can remember. Growing up, he would travel to Seattle to guest play with Crossfire. At thirteen, he moved to the Seattle area full-time to join the U.S. Soccer Development Academy (DA), which has since been replaced by MLS Next.

Bailey was recruited to play Division I soccer at the University of New Mexico, but after the program was eliminated, he transferred to UNLV. He completed his college career at Seattle University. He has also played for Midlakes United and Ballard FC of the USL League Two.

Bailey began coaching to enhance his leadership skills and help the next generation of players develop and achieve their goals. His mentors include his father, Troy, and several staff members from Eastside FC, such as Tom Bialek, Chance Fry, and Jhon Kennedy Hurtado. Bailey appreciates the positive environment at Eastside FC.

His training sessions are designed to be fast-paced, intense, and dynamic, with specific coaching points to maintain focus on play rather than discussion. He aims to instill a love for the game while creating lasting memories and skills.

An avid Arsenal fan, Bailey enjoys watching soccer in his free time. He has recently taken up golf, but when the weather doesn’t cooperate, he likes to unwind with a movie or TV show.