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. He was injured against
Kentucky when the Wildcats' center
Oscar Tshiebwe stepped on his left foot. Bailey aggravated his injury the following game. From December 30, 2022, until January 26, 2023, he was sidelined for seven games due to discomfort in his foot. On February 9, Bailey scored 24 points in a win against
Oregon State. 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. In the Bruins' opener in the
2023 Pac-12 tournament, Bailey scored a career-high 26 points in a win over
Colorado. He had 19 points and seven rebounds in the finals, which UCLA lost 61–59 to Arizona. He was named to the 2023 All-Pac-12 Tournament team. 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. He was named to the Pac-12 All-Freshman Team. After the season, he
declared for the NBA draft.
Re-entry attempt On January 30, 2026, Bailey became the center of a major eligibility and legal controversy after it was reported that he had hired a lawyer and an agent to obtain college eligibility, despite having previously forgoed his eligibility and playing 10 games in the NBA. On February 12, 2026, Bailey visited
Grand Canyon in an official recruiting visit during their game against
New Mexico. ==Professional career==