Holmes starred at North Salem High School. He was named second-team all-state as a junior and first-team all-state as a senior.[1]
Holmes played two seasons for San Francisco and averaged 12.5 points and 3.1 assists per game as a sophomore. In May 2014, he announced he was transferring to Clemson.[1] He averaged 10 points per game as a junior and started all 31 contests.[2] As a senior at Clemson, Holmes averaged 10.3 points, 2.4 rebounds, and 1.3 assists per game.[3]
On September 26, 2017, Holmes was signed by Panionios in Greece.[3]
Holmes was selected in the third round of the 2017 NBA G League draft by the Santa Cruz Warriors and signed with the team. In his first season for Santa Cruz, he averaged 6.2 points and 1.6 assists per game.[4]
In October 2018 he was traded to the Agua Caliente Clippers of the G League for a 3rd round pick.[5] He was placed on waivers on November 1.