Bolden was ineligible to play with the Bruins in his freshman year in 2014–15 after the National Collegiate Athletic Association (NCAA) ruled him a partial qualifier due to his transferring as a high school senior.

He was selected by Philadelphia in the second round of the 2017 NBA draft with the 36th overall pick, but played one season with Maccabi Tel Aviv in Israel before joining the 76ers.

[6] As a teenager, he attended Homebush Boys High School and was first selected to represent his home state of New South Wales at the 2013 Basketball Australia Under 18 National Championships.

[8][9] In August 2013, he relocated to the United States to play as a senior at Findlay College Prep, a private preparatory school in Henderson, Nevada, near Las Vegas.

[16] Before the season, the NCAA declared him a partial qualifier, stemming from his transfer from Australia when his senior year in high school has already began.

[23][24] However, his college debut was delayed after he violated unspecified team rules and was held out of UCLA's season opener, an 84–81 upset loss to Monmouth.

[25] He made his first appearance the following game, making an impact on defense while scoring 11 points and adding five rebounds in an 88–83 win over Cal Poly.

During the offseason, he hoped to move to small forward, the position he was recruited to play, but he remained in a big man role, even with reserve György Golomán healthy again.

[38] On 15 March 2017, Bolden was awarded the ABA League Top Prospect title after averaging 12.9 points and 7.2 rebounds per game in his rookie season.

Before even suiting up for a single regular season game for the Crvena zvezda, on 21 July 2017, Bolden signed a three-year contract with the Israeli club Maccabi Tel Aviv.

[42] On 12 December 2017, Bolden recorded a season-high 23 points, shooting 8-of-14 from the field, along with 10 rebounds, 3 assists and 3 steals in a 98–90 win over Ironi Nahariya.

[48] On 12 February 2020, Bolden was signed to a 10-day contract by the Phoenix Suns, who were without big men Frank Kaminsky, Aron Baynes, Dario Šarić and Deandre Ayton during that time.

[49] Bolden played in two more games for the Suns, which saw all of their big men (minus Kaminsky) return to action before he was not signed for a second 10-day contract on February 24.

[58] In August 2019, Bolden made his senior debut for the Australian Boomers in an exhibition win against Canada leading up to the 2019 FIBA World Cup.