[1] During his undergraduate and law school years, Reeves had summer jobs at a coal mine and General Motors assembly factory.

He was in private practice with the Lexington, Kentucky law firm Greenebaum Doll & McDonald from 1983 to 2001, starting as an associate before being promoted to partner in 1988.

[4] On March 15, 2016, President Barack Obama nominated Reeves for a position on the United States Sentencing Commission, which would expire on October 31, 2021.

[5][6] On July 13, 2016, a hearing on his nomination was held before the Senate Judiciary Committee.

In January 2025, Reeves blocked the Biden administration's Title IX rule, which would have added protections for LGBTQ+ students and strengthened protections for victims of sexual harassment.