Sexuality
Friends from the 1970s confirmed that Billings was homosexual, but not open to discussing it. In 2006, looking back to the Kennedy Administration, Ben Bradlee said: "I suppose it's known that Lem was gay....It impressed me that Jack had gay friends." At the same time, he admitted that no one ever expressed the idea aloud during Kennedy's White House years. 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." One historian wrote that after the 1963 assassination Billings was "Probably the saddest of the Kennedy 'widows.'" Though newspapers often mentioned Billings attendance at major social events, they identified him either as the escort of a member of the Kennedy family or included him in a list of Kennedy friends. Otherwise he attended without a female partner.
Charles Bartlett, a journalist who introduced Kennedy to Jaqueline Bouvier and friend of both Billings and Kennedy, described their relationship: "Lem was a stable presence for Jack. Lem's raison d'ĂȘtre was Jack Kennedy. I don't think it's true that he did not have views of his own, as some have said. He had a very independent mind. He had interests of his own that Jack didn't necessarily share. He certainly didn't have the same interest in politics and women that Jack had." 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." He believed Billings loved Kennedy.
"Jack made a big difference in my life," Billings said. "Because of him, I was never lonely. He may have been the reason I never got married."
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