Bailey grew up in Chicago, Illinois, and was raised by a single mother.[6][7][3] Attending Skinner West Elementary School in the West Loop neighborhood in the Near West Side, he was the most talked about 7th grade basketball player in Chicago.[8][9] In 2017, when he was 12 years old he and his mother were featured when he was in middle school in Bringing Up Ballers, a Lifetime reality show that followed Chicago-area entrepreneur mothers of basketball players.[10][7][11][12]
Bailey was a consensus five-star recruit and one of the top players in the 2022 class, according to major recruiting services. At age 13, while in eighth grade, he committed to playing college basketball for DePaul, but he decommitted before starting high school.[21][22] He later committed to UCLA as a high school freshman, before decommitting again eight months later when their coach, Steve Alford, was fired.[23][24] On February 17, 2021, Bailey recommitted to UCLA and their new coach, Mick Cronin.[24][25]
Bailey was seen as the number one player by every recruiting service entering the summer off his senior season, before he suffered an injury which resulted in Bailey missing playing in the AAU circuit and early parts of Sierra Canyon season.[26]247Sports ranked Bailey as the third-best combo guard in his high school class, and ESPN ranked him the No. 2 shooting guard and No. 5 in the nation among all players in his high school class.[27][17]
Bailey began the 2022–23 season winning the Pac-12 Conference's freshman of the week award twice, and had a couple of 19-point games against Pepperdine and Stanford.[28][29] He was injured against Kentucky when the Wildcats' center Oscar Tshiebwe stepped on his left foot. Bailey aggravated his injury the following game.[30] From December 30, 2022, until January 26, 2023, he was sidelined for seven games due to discomfort in his foot.[28][31][32][33] On February 9, Bailey scored 24 points in a win against Oregon State.[34] After UCLA's best defender, Jaylen Clark, suffered a season-ending leg injury in the regular-season finale, Bailey assumed the task of defending the opposition's top perimeter player, and he also increased his scoring.[35][36][37]
In the Bruins' opener in the 2023 Pac-12 tournament, Bailey scored a career-high 26 points in a win over Colorado.[38] He had 19 points and seven rebounds in the finals, which UCLA lost 61–59 to Arizona.[39] He was named to the 2023 All-Pac-12 Tournament team.[40] He helped the Bruins advance to the Sweet 16 of the 2023 NCAA tournament, averaging 15.5 points and 6.0 assists while converting 49.5% of his field goals and 38.9% of his three-pointers. In the six games after Clark's injury, Bailey averaged 17.3 points and shot 56.1%. He ended the 2022–23 season with averages of 11.2 points, 3.8 rebounds, and 2.2 assists in 30 games, including 28 starts.[41][42] He was named to the Pac-12 All-Freshman Team.[43]
Bailey was selected by the Charlotte Hornets in the second round of the 2023 NBA draft with the 41st overall pick.[42] On July 14, 2023, he signed a two-way contract with the Hornets.[44] Playing for the Hornets in the 2023 NBA Summer League, he averaged nine points in 16 minutes per game, as at 19 years of age he was the 10th-youngest player in the league.[45][46] On November 17, 2023, he made his G-League debut with the Greensboro Swarm, and scored 26 points.[47]
Bailey made his NBA debut on November 12, 2023, for the Hornets against the New York Knicks.[48]