Bailey graduated in 2018 from Loyola University Maryland with a BA in Global Studies. After, he began his political career as a field organizer on Susan Wild's Congressional campaign. Since then, Bailey has been fortunate to work on a Mayoral race, two Presidential cycles for super PACs, and a political compliance firm based in Philadelphia—where he currently lives with his wife. In his free time, he enjoys playing with his cats, reading, video games, or going for a long walk/hike. Being born in Allentown, Bailey is a big lover of the Billy Joel song.