Bailey was the starting keeper for Roots 2020 NISA season, starting both games of the NISA season before the Covid pandemic ended the season early. Taylor was born and raised in Greenville, Tennessee before starting his college career at Nova Southeastern University. After a short time in Florida, Bailey played for San Francisco Community College from 2017-2019 where he led the team as Captain. During the college offseason, Bailey also featured locally for USL League Two side SF City FC. In 2021, Bailey made three appearances, all starts while being on the bench for both playoff games. In 2022 Bailey spent a short portion of the year on loan with Forward Madison. He returned to Oakland to make four appearances with Roots.