Lippitt took a leave of absence from Yale Law School and enlisted in the United States Army on August 6, 1941, four months before the attack on Pearl Harbor.

(Some sources state that he served in the Philippines but this is not mentioned in his official legislative biography in the Rhode Island Manual.

[5] After being released from active duty, Lippitt reverted to inactive status in the National Guard and pursued a private law practice.

He was promoted to lieutenant colonel on February 19, 1957 and retired from the National Guard in 1965, after a total of 24 years of military service.

In addition to his legal career, Lippitt also served as a member of the Board of Trustees of the Providence Institution for Savings (a.k.a.

He was also noted for his influence in the passage of the Rhode Island Fair Housing Act of 1968 and for his unsuccessful opposition to the imposition of a state income tax in 1970.

After Cianci was removed from office following criminal charges in 1984, Democratic City Council chairman Joseph Paolino became acting mayor and a special election was called.

Lippitt entered the race as an independent, running against Paolino, State Representative Keven McKenna and businessman Emmanuel Torti.

In 1985, Lippitt was appointed as the Director of the Rhode Island Department of Administration by the newly elected Republican governor, Edward DiPrete and served in the position until 1988.

Lippitt was an unsuccessful Republican candidate for Lieutenant Governor of Rhode Island in 1988 when he was defeated by Democratic State General Treasurer Roger N. Begin.

He was narrowly defeated (by a margin of only 317 votes) by Cianci, who was permitted to run for office again after serving a five-year suspended sentence.

He also served Chairman of the Rhode Island Board of Governors for Elementary and Secondary Education for several years prior to his death.

He never married and lived with his sister, Mary Ann Lippitt (1918-2006), a pilot who founded her own aviation company after the Second World War.

Mary Ann Lippitt took the first nurse's aide class offered by the Rhode Island Red Cross when she was still a teenager.

In 1944 she was trained as a pilot and worked as a flying instructor in Virginia and served in the U.S. Air Postal Service during the war.

In 1946 she formed Lippitt Aviation, and was one of the first woman business owners in Rhode Island and operated a charter service.

On January 19, 2006 Lippitt was posthumously inducted by Mayor of Providence David Cicilline into the Reverend Martin Luther King Hall of Fame.