Billings was a preparatory school roommate of Kennedy, an usher at his wedding, and a campaigner for his successful 1960 presidential bid.

His mother was a Mayflower descendant and his great-grandfather, Francis Julius LeMoyne, was a prominent abolitionist linked to the underground railroad who helped establish what is today known as LeMoyne–Owen College, and was responsible for constructing the first crematorium in the United States.

[4] In 1939, Billings graduated from Princeton University, majoring in art and architecture[5] and wrote his senior thesis on Tintoretto.

[6][7] In 1941, Billings failed medical tests required for admission to the U.S. military during World War II.

[8] In 1942, supported by a recommendation from Joseph P. Kennedy Sr., was accepted by the AFS ambulance service, where his poor eyesight was not a disqualification.

[11] After working on John F. Kennedy's successful campaign for U.S. Congress in 1946, Billings toured seven Latin American countries with Robert F.

[13] He later had several jobs, including selling Coca-Cola dispensers to drugstores and working at a General Shoe store.

As Vice President at the Emerson Drug Company in Baltimore, he invented the 1950s fad drink Fizzies by adding a fruit flavor to disguise the sodium citrate taste.

[16] On September 12, 1953, Billings was an usher at the wedding of John F. Kennedy and Jacqueline Lee Bouvier.

[19] In 1961, Billings declined Kennedy's offers to appoint him the first head of the Peace Corps, director of a new agency to promote tourism, the U.S. Travel Service, or ambassador to Denmark.

[21][22] The next year, Kennedy named Billings to the board planning America's participation in the New York World's Fair of 1964–1965.

"[29] Historian Sally Bedell Smith compared him to Leonard Zelig, a nondescript character in Woody Allen's 1983 film who is always present in the back row at major events.

[35] In 1962, he escorted two of the President's sisters, Eunice Shriver and Jean Kennedy Smith, around Europe for two weeks.

"[27] Arthur Schlesinger thought Billings "used to glare at me when we occasionally encountered each other in the company of JFK, and for a time I took this rather personally.

[51] Red Fay, a friend of the President from his World War II service, said of Billings: "I didn't see anything overtly gay about him; I think he was neutral.

[55] Kennedy knew that gay behavior on the part of Billings had been revealed by a fellow Choate student during their years there.

"[58] Though Gore Vidal thought Billings was "absolutely nobody," he also believed "it was a good idea that Jack had somebody he could trust like that around him."

[62] After the assassination of Robert F. Kennedy in 1968, Billings became depressed and started to drink in excess, an addiction that plagued him for most of his life.

[66] The elder Kennedys began to discourage the boys from associating with Billings because of his excessive recreational drug use (including alcohol).

[63] Billings served for many years along with Sargent Shriver as a trustee for the Kennedy family trusts,[67] working from an office in the Pan Am Building.

[65] Jacqueline Kennedy Onassis included Billings as a guest at a party marking the birthdays of her children Caroline (21st) and John Jr. (18th) in 1978.

His dying wish was for the young Kennedy men to carry his casket to its final resting place.