Fair, a Baltimore Sun First-Team All-Metro selection, helped lead City College to a 25–4 record and a berth in the state regional semifinals as a sophomore.

[1] He missed his junior season in high school due to a knee injury, and later committed to Syracuse University in October 2008.

[10] Five days later, he was acquired by the Fort Wayne Mad Ants of the NBA Development League as an affiliate player of the Pacers.

[12] After joining the Boston Celtics for the NBA Summer League,[13][14] on September 15, 2015, Fair signed with the Indiana Pacers, returning to the team's training camp for the second year in a row.

[20] On February 12, 2018, Fair was traded by the Fort Wayne Mad Ants to the Windy City Bulls in exchange for Duje Dukan and the returning player rights to Henry Sims.

In five games, he averaged 8.6 points, 6.6 rebounds and 1.4 steals to help lead Boeheim's Army to the Semifinal Round where they fell 81–77 to the eventual champions Overseas Elite.