From 1999 to 2004, he served as an assistant state's attorney in the Connecticut Division of Criminal Justice.

[4] During his tenure on the Connecticut Superior Court, Oliver chaired the Committee on Judicial Ethics.

He served on the State Wiretap Panel and co-chaired the Connecticut Sentencing Commission.

President Biden nominated Oliver to the seat vacated by Judge Stefan R. Underhill, who assumed senior status on November 1, 2022.

[10] On September 18, 2023, the United States Senate invoked cloture on his nomination by a 54–40 vote.