Bailey was born on the Hoopa Valley Indian Reservation in Northern California. Raised by a young single mother and large extended family, Bailey grew up hearing the stories of his people. From his home on the Trinity River, he could see the dance grounds where renewal ceremonies are held. From as long as he can remember, Bailey drew the stories he heard, landscape he saw, and scenes he imagined.
Bailey is a graduate of Western Oregon University and earned a Masters from the University of Oregon. He was recruited by Chemawa Indian School, the oldest continually operating federal boarding for Native American students, to reimagine their “Indian Crafts” program as a fine arts curriculum. Bailey was inspired by the students who come from tribes throughout the nation and was energized by the pan-Indian culture of the school. He taught at Chemawa for 40 years. He retired from Chemawa in 2018.
Bailey maintained a studio and painted during the evening and weekends during his teaching career. His work often begins with an archival photograph of Native Americans, typically one the photographer intended as a “document of a vanishing race.” He recontextualizes the static, sometimes staged portraits with layers of color, traditional Native design, contemporary cultural references, documents and landscapes, real and imagined. About his body of work, Bailey states, “I paint our ancestors so people today will know our past to tell our stories in the future.”