From 1802 to 1807, Livingston served as a justice of the Supreme Court of New York, where he authored a famous dissent in the 1805 case of Pierson v. Post. Two years later, on November 10, 1806, Livingston received a recess appointment to the Supreme Court of the United States from Thomas Jefferson, to a seat vacated by William Paterson. Formally nominated on December 15, 1806 as Jefferson's second nominee, Livingston was confirmed by the United States Senate on December 17, 1806, and received his commission on January 16, 1807. He served on the Supreme Court from then until his death in 1823. During his Supreme Court tenure, Livingston's votes and opinions often followed the lead of Chief Justice John Marshall. In that era, Supreme Court Justices were required to ride a circuit; in Justice Livingston's case, he presided over cases in New York State.
Virginia-New York Alliance
Prior to his appointment to the U.S. Supreme Court, Livingston served as a judge for the State Supreme Court of New York, a member of the New York State Assembly, and an immensely prominent political activist. Due to family ties, Livingston's allegiance to the Democratic-Republican party soon faded. Essentially, Livingston rebelled and goaded the Federalists to an enormous extent. With members consisting of Aaron Burr, Robert R. Livingston, and Edward Livingston, Livingston became one of the few emerging from a compact political faction in New York to form an alliance with Jefferson's supporters in Virginia. This became known as the Virginia-New York alliance, which proved to be vital in Jefferson's 1800–1801 election.
Livingston married three times. He first married Catherine Keteltas, the daughter of Peter Keteltas and Elizabeth Van Zandt, on December 2, 1784. He and Catherine were the parents of:
Eliza Livingston, who married Jasper Hall Livingston, the son of Philip Philip Livingston
Susan French Livingston, who married Benjamin Ledyard.
Catherine Augusta Livingston, who married Archibald McVicker
Robert C. Livingston
After his first wife's death in 1804, he married Ann N. Ludlow, the daughter of Gabriel Henry Ludlow and Ann Williams. Together, they were the parents of:
Carroll Livingston, who married Cornelia Livingston.
After his second wife's death in 1815, he married Catherine Seaman, the daughter of Edward Seaman and the widow of Capt. John Kortright. Together, Henry and Catherine were the parents of:
Catherine Louise Livingston, a twin, who married Maurice Power, an Irish MP for County Cork who served as Lieutenant Governor for St. Lucia.
Henry Brockholst Livingston, who married Marianna Gribaldo and resided in Italy.
Descendants
Through his daughter Eliza, he was the great-grandfather of Edwin Brockholst Livingston, a historian. Through his daughter, Susan, he was the grandfather of Henry Brockholst Ledyard and great-grandfather of Lewis Cass Ledyard. Through his daughter, Catherine McVicker, he was the grandfather of Brockholst McVicker and Archibald McVicker. Through his daughter, Catherine Power, he was the grandfather of: Brockholst Livingston Power, John Livingston Power, and Alice Livingston Power. Through his son, Henry, he was the grandfather of Oscar Enrico Federico Livingston. Through his son Anson, he was the grandfather of Ludlow Livingston, Mary Allen Livingston Harrison and Ann Ludlow Livingston.