Born in Watertown, New York, Blakeney was a 2015 McDonald's All-American and Florida's Mr. Basketball. He finished the 2014-15 season averaging 29 points, 6.9 rebounds as well as 2.7 assists for Oak Ridge High School in Orlando, Florida. Blakeney was rated as a 5 star recruit by Rivals, ESPN, and 247 Sports. Rivals had him as the #13 overall recruit, while ESPN had him at #15 and 247 at #16. Both ESPN and 247 ranked him as the #3 SG in the nation.
College career
Blakeney initially gave a verbal commitment to the University of Louisville, but then Blakeney changed his mind about 10 days later and decommitted. Blakeney ended up committing to Louisiana State University. At Louisiana State University he was featured in 34 games as a freshman, playing alongside Ben Simmons. Behind Simmons and Keith Hornsby, Blakeney was LSU's third-leading scorer in 2015-16, averaging 12.6 points a contest, hitting a team-best 52 three-point shots on the season. The 2016–17 season saw him emerge as LSU's leading scorer, pouring in 17.2 points per contest, while corralling 4.8 rebounds a game and handing out 1.7 assists per outing. Blakeney took home an All-SEC Second Team selection that year. In April 2017, he announced to forgo the remaining two years of his eligibility and declared for the 2017 NBA draft.
After going undrafted, Blakeney joined the Chicago Bulls for the 2017 NBA Summer League. Based on his performance there, Blakeney was signed to a two-way contract by the Bulls. Under the terms of the deal, he split time between the Bulls and their G League affiliate, the Windy City Bulls. He made his professional debut with Chicago on October 19 against the Toronto Raptors. On November 21, 2017, Blakeney scored 15 points in 18 minutes off the bench in a 113-105 loss to the Los Angeles Lakers. He won the NBA G League Rookie of the Year Award for his time with the Windy City Bulls. On July 19, 2018, Blakeney was signed to an NBA contract by the Bulls. In the season opener on October 18, 2018, Blakeney scored 15 points off the bench in a 127–108 loss to the Philadelphia 76ers. In a 107-105 loss to the Indiana Pacers on November 2, 2018, Blakeney scored a career-high 22 points off the bench. On September 9, 2019 Blakeney was released by the Bulls.