Sometimes the significance of an item in the news can sometimes be measured by how little attention it attracts. To see how far the cause of gay rights has progressed in such a remarkably short period of time, consider the following sentence buried in an otherwise banal Associated Press report about Barack and Michelle Obama’s vacation plans over the recent Father’s Day Weekend in Rancho Mirage, California. “They are staying with White House decorator Michael Smith and his partner, U.S. Ambassador to Spain James Costos, at their vacation home.”

Not long ago, the notion of the First Couple spending a long weekend with a gay one, let alone advertising it to the press, would have presented the White House Chief of Staff with a PR headache. Would the public read too much into it? Would it signal support for same-sex marriage? How will it play in Peoria? Now, nobody bats an eye.

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American presidents have long had gay friends and advisers, many of whom have occupied positions not so stereotypically swish as White House decorator. One could conceivably start the list with Rufus King, who served as Vice President to Franklin Pierce, and is speculated by some historians to have been the lover of President James Buchanan. More often than not, however, their homosexuality was a closely guarded secret, revealed unintentionally or as a result of embarrassing scandal. It is only very recently that the leader of the free world has felt secure enough to let it be known that he’s friends with friends of Dorothy.

Washington has long attracted a disproportionate number of gay people, a phenomenon that really took off with the city’s massive expansion as the seat of federal bureaucracy during World War II. (The Advocate magazine recently lauded Washington as the most gay-friendly city in the country and The New York Times, utilizing census data, has deemed it the “gayest place in America”). Government service often requires long hours away from home and unquestioning loyalty to one’s boss, job requirements that gay men in particular, generally free from the constraints of traditional family life, have been adept at filling. Here is a (by no means exhaustive) list of presidents and some of their gay consligieres:

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Dwight Eisenhower and Arthur Vandenberg Jr.

Arthur Vandenberg Jr., the son of a Michigan Senator, was preparing to start a senior job in the administration of incoming President Dwight Eisenhower when the FBI informed him that his future as a White House staffer was not to be. J. Edgar Hoover, the agency’s director, had come into possession of compromising material about Vandenberg, information he was keeping as part of the Sex Deviates Program that would ruin the careers of thousands of gay men and women (as well as those whose homosexuality was merely presumed) over the course of nearly 25 years. “Arthur wasn’t a fighter,” wrote Dudley Clendinen, Vandenberg’s godson. “He folded. He checked into a hospital, complaining of stomach problems, and resigned the appointment for ‘health reasons’ three months after Eisenhower’s inauguration.”

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In a May, 1953 letter to Vandenberg, Eisenhower wrote, “I want to make the personal request that whenever you may come to this city you make it a habit to give my office a ring, so that we may arrange at least a short meeting.” Three years later, the scandal magazine Confidential, likely working in collusion with the FBI, published an expose of Vandenberg’s alleged gay trysts. Despite all his work on Eisenhower’s successful presidential campaign, Vandenberg was relegated to a footnote in Eisenhower’s memoir.

John F. Kennedy and Lem Billings and Joe Alsop

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From his schoolboy days at the tony New England prep school Choate until his death by an assassin’s bullet 30 years later in Dallas, John Fitzgerald Kennedy’s best friend was Kirk LeMoyne Billings, also known as “Lem.” According to Jack and Lem, a 2008 book about their friendship, Billings made a pass at the future president while the two were students. “I’m not that kind of boy,” Kennedy told him. Most men in that place and time—it was the early 1930’s—would have ended the relationship immediately. But the two remained close, traveling through Europe after graduating high school (Joe Kennedy Sr. referred to Billings as “a second son.”) Billings worked on Kennedy’s successful 1960 presidential campaign, but declined prestigious job offers including leadership of the newly created Peace Corps. Nonetheless, he was such a frequent visitor to the White House during the Kennedy administration that he had his own room.

Though Billings was discreet about his sexual orientation, it was well known throughout Washington. Kennedy’s unconcern about Billings crashing 1600 Pennsylvania Avenue most weekends might have been due to the fact that, as an infamous lothario himself, he didn’t worry that close friendship with a gay man would generate suspicions of homosexuality.

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JFK’s other gay friend was one of the most famous men in Washington at the time, but also one of its most closeted. Joseph Alsop was a distant cousin of Franklin D. Roosevelt, and, with his brother Stewart, penned a thrice-weekly column, “Matter of Fact,” which appeared in some 200 newspapers across the country. A virulent anti-communist and ardent supporter of the Vietnam War, Alsop was the most prominent journalist to push the supposed “missile gap” between the Soviet Union and America, a term skillfully used by Kennedy to paint the incumbent Eisenhower administration and its Vice President, presidential contender Richard Nixon, as soft on communism. Alsop’s exterior toughness against the Soviets, which masked a deep secret, has led some historians to conclude that he was compensating for his hidden homosexuality. “During his early career as a congressman, Jack had been a guest at a number of Alsop’s dinner parties, until his flippant remark that there never seemed to be any pretty girls in attendance irritated Alsop, who cut off further invitations,” writes Barbara Lemming, author of a biography of Jackie Kennedy.

On a 1957 trip to Moscow, Alsop was entrapped by a handsome young KGB spy and the incident was caught on camera. Confronted with the evidence, Alsop refused to become a Soviet spy, and immediately told his editors and the CIA about what had happened. Such was the Washington rumor mill at the time and the nature of the capital “E” Establishment, that many powerful people in the capital, including Kennedy, knew about Alsop’s secret but refused to divulge it. When, in 1970, after a particularly bruising series of anti-Soviet columns, the Russians sent envelopes containing photos of the 1957 encounter to Washington journalists—including two of Alsop’s many nemeses—none of the recipients publicized the information. Columnist Art Buchwald, then engaged in a long-running feud with Alsop, tore the photos up.

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Lyndon B. Johnson and Walter Jenkins

Decades before Idaho Senator Larry Craig’s political career would end in shame over a foot-tapping scandal in an airport restroom, there was the sad case of Walter Jenkins. Lyndon B. Johnson once referred to Jenkins as “my Vice President in Charge of Everything.” Jenkins joined Johnson’s employ at the age of 21 when the latter was a congressman, and served alongside him for his entire adult life. On October 7, 1964, Jenkins attended a Newsweek party celebrating the opening of its bureau in Washington, D.C. Tipsy, he walked to the YMCA near the White House.

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The bathroom, a notorious cruising scene at the time, was under surveillance by D.C. police, who arrested Jenkins and his sex partner almost immediately after the two entered a toilet stall. Hoping the matter would go away (he had been arrested, in the same bathroom, in 1959), Jenkins pled guilty to the charge of lewd conduct and didn’t even hire a lawyer. But the story inevitably broke in the press. “There can be no place on the White House staff or in the upper echelons of government for a person of markedly deviant behavior,” remarked the now stridently pro-gay New York Times editorial board. Jenkins promptly resigned and checked into a hospital for “exhaustion.”

Richard Nixon and… Nobody

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Thanks to recently released transcripts of Richard Nixon’s White House conversations, we know for sure what had been long-suspected: that in addition to blacks, Jews and other minority groups, Nixon wasn’t particularly fond of gays. Discussing the popular television program All in the Family, Nixon was incredulous at a positive portrayal of gay characters. “They were glorifying homosexuality!” he exclaimed in a 1971 conversation with advisers John Ehrlichman and Bob Haldeman. “You ever see what happened, you know what happened to the Greeks? Homosexuality destroyed them. Aristotle was a homo. So was Socrates.” After Ehrlichman, ever the obsequious minion, egged on his boss by remarking that the Greek philosopher “never had the influence that television has,” the pseudo-historian president replies indignantly that, “The last six Roman emperors were fags. You see, homosexuality, immorality in general, these are the enemies of strong societies. That’s why the communists and the left-wingers are pushing it. They’re trying to destroy us.”

With these views, it doesn’t come as a surprise that Nixon did not have any known, openly gay friends or advisers. But a 2011 book speculates that Nixon may have had a gay affair. In Nixon’s Darkest Secrets: The Inside Story of America’s Most Troubled President, author Don Fulsom speculates that Nixon had a relationship of a “possibly homosexual nature” with his best friend, Charles “Bebe” Rebozo. Fulsom proffered little evidence to buttress his claim; a former Time reporter who claimed to have seen the men holding hands under a dinner table, another journalist who saw Nixon put his arm around Rebozo “the way you’d cuddle your senior prom date.” Mark Feldstein, author of another book about Nixon and a journalism professor at the University of Maryland, attributed this most improbable of historical outings as the result of gossip refracted through the controversies of our cultural moment, coming as it did amidst a time when “homosexuality has come out of the closet and same-sex marriage has become a prominent part of the legislative agenda in many places.”

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Gerald Ford and Oliver Sipple

Gerald Ford and his gay best friend sealed their bond on September 22, 1975. On that day, five-time divorcee Sarah Jane Moore pulled a gun on the president as he exited the St. Francis Hotel in San Francisco (it was a bad month for Ford, just three weeks earlier, another disturbed woman, Lynette “Squeaky” Fromme, tried to assassinate him in San Francisco, but a Secret Service Agent forced the gun from her hand). Had Oliver Sipple not grabbed Moore’s hand as she fired, directing the bullet away from the president, Ford likely would have been gravely injured, if not killed.

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Sipple’s homosexuality was revealed by San Francisco Chronicle columnist Herb Caen, who had heard the ex-Marine was a friend of Harvey Milk, an openly gay man then running for a seat on the city’s Board of Supervisors. In the Mayor of Castro Street, his biography of Milk, author Randy Shilts reported that that the budding politician thought the world should know of Sipple’s sexual orientation so that, “for once we can show that gays can do heroic things.”

That a gay man would save a president’s life was ironic. Just three years earlier, newspaper columnist Jack Anderson revealed that the Secret Service had compiled a list of 400 organizations that it monitored “to prevent political assassinations.” On the list: the Gay Liberation Front.

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Ronald Reagan and Rock Hudson

Ronald and wife Nancy Reagan became friends with many gay people during their years in Hollywood. One of the most prominent was Rock Hudson, the matinee idol whose public image as a heartthrob disguised his homosexuality. In 1984, Hudson was diagnosed with HIV, a fact that he would not disclose until over a year later. This was at a time when the disease had just begun to ravage the gay community and many were criticizing the Reagan administration for its slow response to the epidemic. The following July, Hudson traveled to Paris for medical treatment and announced, through a publicist, that he had AIDS.

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While Reagan made no official statement about his friend’s illness (his first public reference to the disease was in September 1985, over two years after its existence had been reported on by the New York Times) Reagan called Hudson at the hospital in Paris and Nancy phoned then-French President Francois Mitterand to guarantee that her friend was receiving top-notch treatment. A 2003 television docudrama initially planned to air on CBS, The Reagans, portrayed Reagan as a virulent homophobe, who tells Nancy, in a conversation about AIDS patients, “They that live in sin shall die in sin.” When the script leaked, Hudson’s former lover Marc Christian wrote an open letter to CBS television President Les Moonves, explaining, “The notion that President Reagan was a homophobe strikes me as silly beyond belief… The point is Reagan could have ignored Rock’s illness and didn’t.”

George H.W. Bush: First President to serve as witness to same-sex marriage

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George H.W. Bush effectively became the fourth sitting or former U.S. President to endorse gay marriage (following presidents Carter, Clinton and Obama) when, with his wife Barbara, he served as an official witness at the wedding of Bonnie Clement and Helen Thorgalsen. (This leaves his son, George W. Bush, as the only living ex-president not to support gay marriage.) His office tried to downplay any attempt at deciphering a political message from the event, with a representative issuing a statement that the Bushes “were private citizens attending a private ceremony for two friends.” The lesbian pair owns a general goods store in Kennebunkport, Maine, where the Bush family has long maintained a vacation residence.

Bill Clinton and David Mixner

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David Mixner met Bill Clinton in 1969 when the two men were young activists in the anti-war and civil rights movements, and was immediately entranced. “His extraordinary talent for ‘connecting’ was irresistible,” he wrote in his memoir, Stranger Among Friends. From that moment, Mixner dedicated himself to Clinton’s political career, working on his every election from a 1974 congressional race to his 1992 presidential victory. But Mixner would come to feel betrayal almost immediately once Clinton passed the “Don’t Ask, Don’t Tell” regulation banning openly gay people serving in the military, after having specifically promised to lift such restrictions. Mixner protested the law and was arrested outside the White House. The two later made amends, but Mixner supported Barack Obama over Clinton’s wife Hillary in the 2008 Democratic presidential primary.

George W. Bush and Charles Francis

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Charles Francis came out to his friend, then-Texas Governor George W. Bush, in a letter. His brother had served as Bush’s campaign chairman and Francis figured he could leverage his personal connection to the governor to help further the cause of gay rights among Republicans. “The day he got the letter, he called me,” Francis told Out magazine in 2001. “Our friendship couldn’t be stronger.” Francis famously organized a meeting for Bush with a group of gay Republicans (dubbed “The Austin 12”) during the 2000 presidential campaign, from which Bush emerged saying he had become “a better person.” Francis later founded the Republican Unity Coalition, a group of gay and straight Republicans that claimed Mary Cheney and former Wyoming Senator Alan Simpson as members.

But, like Mixner, Francis’s friendship with a president would be tested once politics entered the fray. In 2004, Bush endorsed a constitutional amendment banning gay marriage—leading many of the prominent gay Republicans who met with him four years earlier to renounce their support for his re-election. “The stampede you hear will be 1 million gay voters who voted for President Bush—gone, and their families gone, and their friends gone,” an indignant Francis told the San Francisco Chronicle that year. Francis dropped his GOP registration and has since reconstituted the Washington Mattachine Society, one of the country’s first gay rights organizations, dedicated to “archive activism” that exposes, through official documentation, the federal government’s historic persecution of gay people.

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