He played college basketball for the University of Montana, where he was named Big Sky Conference Defensive Player of the Year in 2012 and 2013.

Cherry had a short stint in the NBA with the Cleveland Cavaliers before playing in Lithuania, Germany, Turkey, Croatia, Greece and Italy.

As a senior, he averaged 12.0 points, 8.0 rebounds, 5.0 assists, and a league-leading 4.0 steals per game for the undefeated (33–0) Warriors, going on to be named league and team MVP.

[12] In July 2015, Cherry joined the San Antonio Spurs for the 2015 NBA Summer League.

In August 2016, Cherry signed with Gaziantep Basketbol of the Turkish Basketball Super League.

On April 13, 2019, Cherry signed with Olympiacos of the Greek Basket League for the rest of the season.

[21] In 2021, Cherry played one game for Hapoel Eilat of the Israeli Basketball Premier League.