He is best known for his service as United States Attorney for the District of Vermont from 1977 to 1981, managing the successful 1986 reelection campaign of U.S.

[1] In 1977, Gray left the director's position to become United States Attorney for the District of Vermont during the presidential administration of Jimmy Carter.

[1] Among the notable prosecutions Gray handled as U.S. Attorney was the controversial 1978 case of Kristina Berster, who had been arrested at the U.S.-Canada border in Vermont and was accused by the government in West Germany of being a member of the Red Army Faction terrorist group.

[8] No links to terrorism were proved, but there were allegations of illegal surveillance and false testimony made against U.S. law enforcement agencies.

[11][12] Gray also prosecuted Gerald Bull, an engineer and weapons designer who operated Space Research Corporation of North Troy.

[6] Bull and a colleague were convicted of illegally selling arms to South Africa in 1980 and served prison sentences.

[6] In 1988, Gray won the Democratic nomination for the U.S. Senate seat being vacated by the retiring Robert Stafford.

[1] In 1993, Leahy and Jeffords recommended Gray to serve as a judge on the United States Court of Appeals for the Second Circuit, the same seat once held by Sterry Waterman.

[3] In addition to his legal practice, he raised sheep, kept bees, and grew Christmas trees and apples.