[1] Between graduating from college in 1984 and beginning law school in 1986, Roberts was a legislative aide for then-Congressman Charles Schumer.
After law school, from 1989 to 1990, Roberts clerked for then-Judge Ruth Bader Ginsburg on the U.S. Court of Appeals for the District of Columbia Circuit.
He briefly left the Department of Justice to work at law firm O'Melveny & Myers but soon returned to his position as Assistant.
Between October 2000 and April 2010, Roberts was one of the ten lawyers who argued the greatest number of cases.
[4][5][6] In 2017, Roberts left OLC to serve as Special Counsel to the US Sentencing Commission.