After a season of college basketball with the Kentucky Wildcats, he was selected by the Oklahoma City Thunder with the 18th overall pick in the 2010 NBA draft and subsequently traded to the Los Angeles Clippers.

As a senior in 2008–09, he averaged 20.3 points, 9.4 rebounds and 11.5 assists per game, and helped lead Parker to a 5A state championship runner-up finish.

[2] Bledsoe played one season at Kentucky in 2009–10, and averaged 11.3 points, 3.1 rebounds and 2.9 assists in 37 games (35 starts) to help the Wildcats to a 35–3 record and Elite Eight appearance.

[5] In September 2010, it was reported that Bledsoe may have been ineligible to play his one season for Kentucky when discrepancies were found in his high school transcripts.

[6] The Alabama Public School System hired the independent law firm of White Arnold & Dowd to investigate claims that one of Bledsoe's grades was improperly changed.

He was subsequently selected with the 18th overall pick in the 2010 NBA draft by the Oklahoma City Thunder, but was traded to the Los Angeles Clippers.

In his second season, due to the Clippers' acquisition of Chris Paul, he played only an average of 11 minutes per game, with only one start, and his stats dropped.

[10] On his opening night debut with the Suns, Bledsoe helped the team by getting 22 points, 6 rebounds, and 7 assists in a 104–91 victory over the Portland Trail Blazers.

Bledsoe also got his first double-double with the Suns by scoring 16 points, grabbing 11 rebounds, and putting up 7 assists in a blowout 117–90 victory over the Los Angeles Lakers on December 23, 2013.

[15] On December 8, 2014, Bledsoe recorded his first career triple-double with 27 points, 11 rebounds and 16 assists in the 120–121 overtime loss to his former team, the Los Angeles Clippers.

[18] On February 26, 2015, Bledsoe recorded a near triple-double with 28 points on 11-of-16 shooting, 13 rebounds, and 9 assists, as well as 4 blocks and a steal in a 117–113 overtime win over the Oklahoma City Thunder.

[22] On December 13, in a win over the Minnesota Timberwolves, Bledsoe recorded 23 points with nine assists plus four steals and tied a career-high with four blocked shots.

[24] On December 29, he underwent successful surgery to repair a torn meniscus in his left knee and was subsequently ruled out for the remainder of the 2015–16 season.

[27] On November 2, he scored 20 points and hit the game-winning three-pointer in overtime to give the Suns their first win of the season with a 118–115 victory over the Portland Trail Blazers.

[37] In the Suns' last game before the 2017 NBA All-Star Weekend, on February 15, Bledsoe recorded his third career triple-double with 25 points, 10 rebounds, and 13 assists in a 137–101 win over the Los Angeles Lakers.

On October 22, 2017, just three games into the season, Bledsoe tweeted out "I Dont wanna be here", which Suns general manager Ryan McDonough took as a slight against the organization and dismissed him from playing with the team.

[42] On November 7, 2017, Bledsoe was traded to the Milwaukee Bucks in exchange for Greg Monroe and a protected first and second-round draft pick.

[53] On December 14, 2019, the Milwaukee Bucks announced that Bledsoe had suffered from a right fibula avulsion fracture during a 127–114 seasons win over the Memphis Grizzlies and was expected to be sidelined for about two weeks.

[57] On August 7, 2021, Bledsoe was traded along with Steven Adams, the draft rights to Ziaire Williams and Jared Butler, and a 2022 protected first round pick to the Memphis Grizzlies in a three team deal with the Charlotte Hornets.

[60] On February 4, 2022, Bledsoe was traded, alongside Keon Johnson, Justise Winslow and a 2025 second-round pick, to the Portland Trail Blazers in exchange for Norman Powell and Robert Covington.