Bailey originally committed to the Bruins and then-coach Steve Alford as a high school freshman, but he decommitted eight months later. Bailey also once committed to DePaul before starting eighth grade, but he decommitted before he entered high school.
Bailey, a 6-foot-4 shooting guard from Sierra Canyon High School (California), is ranked No. 3 in the ESPN 60 for the 2022 class.
"He's a pure combination guard who has effortless high-end scoring ability with or away from the ball," said Paul Biancardi, ESPN's national recruiting director. "His jump shot displays balance and accuracy from a variety of spots on the floor. I like his self-confidence to make contested shots when needed. His drive game and paint finishes end with explosive athleticism and body control. As a playmaker, he is equally adept at creating for himself or facilitating for others. In transition or in the halfcourt, he demonstrates outstanding passing vision."
The No. 1 shooting guard in the 2022 class, Bailey helped lead USA Basketball to a gold medal at the 2019 FIBA Americas U16 Championship in Brazil. He started all six games at that event, averaging 13.2 points, 4.2 rebounds and 3.0 assists.
"He's a clever ball handler who changes his speeds and direction with purpose when navigating a defense," Biancardi said. "He's somewhat underrated as a versatile backcourt defender who will rebound and start the fast break. He owns an on-court presence and offensive instincts that remind me of D'Angelo Russell."
Bailey is coach Mick Cronin's first commitment in the 2022 class, but he's also a candidate to reclassify to the 2021 class. If he does move up and enroll at UCLA, Bailey would join a class that includes five-star small forward Peyton Watson and ESPN 100 shooting guard Will McClendon.
The Bruins' 2021 class is ranked No. 7 in the country; if Bailey reclassifies, it would vault into the top five nationally.