Secret City: The Hidden History of Gay Washington

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For my family

and

for all those who unburdened themselves of their secret,

so that I did not have to live with mine

A reprobate part of the human whole, but an important part, suspected where it does not exist, flaunting itself, insolent and unpunished, where its existence is never guessed; numbering its adherents everywhere, among the people, in the army, in the church, in the prison, on the throne; living, in short, at least to a great extent, in a playful and perilous intimacy with the men of the other race, provoking them, playing with them by speaking of its vice as of something alien to it; a game that is rendered easy by the blindness or duplicity of the others, a game that may be kept up for years until the day of the scandal, on which these lion-tamers are devoured; until then, obliged to make a secret of their lives …

—Marcel Proust, Sodom and Gomorrah

There are two histories: the official, lying history, which is taught in schools, history ad usum Delphini; and the secret history, in which the real causes of events are set forth—a shameful history.

—Honoré de Balzac, Scenes from Provincial Life

DRAMATIS PERSONAE

Franklin Delano Roosevelt

Gustave Beekman: Brooklyn brothel owner

William Christian Bullitt Jr.: Ambassador to the Soviet Union (1933–36) and France (1936–40)

Juan Francisco de Cárdenas: Spanish ambassador to the United States

William Wild Bill Donovan: Director, Office of Strategic Services (OSS)

Donald Downes: OSS operative

Allen Dulles: Head of OSS Bern office; director, Central Intelligence Agency (1953–61)

Morris Ernst: General counsel, American Civil Liberties Union and the New York Post

Lorena Hick Hickok: Reporter, Associated Press

J. Edgar Hoover: Director, Federal Bureau of Investigation

Cordell Hull: Secretary of state

Odessa Madre: Female Al Capone of Washington, DC

Eleanor Josephine Medill Cissy Patterson: Publisher, Washington Times-Herald

Carmel Offie: Aide to Ambassador William C. Bullitt; CIA officer

Drew Pearson: Syndicated columnist, Washington Merry-Go-Round

Baron Wolfgang Gans zu Putlitz: Anti-Nazi German diplomat and spy

Dorothy Schiff: Publisher, New York Post

Clyde Tolson: Associate director, FBI

David Walsh: Senator (D-MA)

Sumner Welles: Undersecretary of state

Harry Truman

Joe Alsop: Syndicated columnist, Matter of Fact

James Jesus Angleton: Chief of the office of special operations, CIA

Roy Blick: Director of the Morals division, Metropolitan Police Department

A. Marvin Braverman: Lawyer and walker of Margaret Truman

Guy Burgess: British diplomat and Soviet spy

Whittaker Chambers: Former Soviet spy; senior editor, Time

Francis Flanagan: Chief counsel, Senate Permanent Subcommittee on Investigations

Alger Hiss: State Department official

Clyde Hoey: Senator (D-NC)

Joe McCarthy: Senator (R-WI)

Kenneth Wherry: Senate minority leader (R-NE)

Dwight Eisenhower

Charles Chip Bohlen: Ambassador to the Soviet Union

Roy Cohn: Chief counsel, Senate Permanent Subcommittee on Investigations

Robert Cutler: Assistant to the president for national security affairs

John Foster Dulles: Secretary of state

Robert Gray: Appointments secretary; secretary of the cabinet

Lester Hunt: Senator (D-WY)

Franklin Kameny: President, Mattachine Society of Washington, DC

William Martin: Cryptologist, National Security Agency

R. W. Scott McLeod: Assistant secretary of state for security and consular affairs

Bernon Mitchell: Cryptologist, National Security Agency

John C. Montgomery: Finnish desk chief, State Department

Margaret Scattergood: Researcher, American Federation of Labor

G. David Schine: Consultant, Senate Permanent Subcommittee on Investigations

Florence Thorne: Director of research, American Federation of Labor

Arthur Vandenberg Jr.: Appointments secretary-designate to the president

John F. Kennedy

Kirk LeMoyne Lem Billings: Best friend of President Kennedy

Ben Bradlee: Newsweek bureau chief (1957–65); Washington Post executive editor (1968–91)

Eva Freund: Early member of the Mattachine Society of Washington, DC

John Nichols Sr.: Special agent, Federal Bureau of Investigation; father of Jack Nichols

John Jack Nichols Jr.: Cofounder, Mattachine Society of Washington, DC

Bayard Rustin: Chief organizer of the 1963 March on Washington for Jobs and Freedom

Gore Vidal: Author and playwright

Lilli Vincenz: First lesbian member of the Mattachine Society of Washington, DC

William Walton: Chairman, U.S. Commission of Fine Arts

William Wieland: Director, Office of Middle American Affairs, State Department

Herman Lynn Womack: Publisher, Guild Press

Lyndon B. Johnson

Katharine Graham: Publisher, Washington Post

Walter Jenkins: Special assistant to the president

Bill Moyers: Special assistant to the president

Robert Waldron: Legislative assistant to Congressman Homer Thornberry and, later, Representative J. J. Jake Pickle

Richard Nixon

Dwight Chapin: Deputy assistant to the president

Murray Chotiner: Nixon political strategist

John Ehrlichman: White House counsel

H. R. Bob Haldeman: White House chief of staff

Steve Martindale: Lawyer and socialite

Robert Robbie Merritt: FBI informant

Ray Price: Special assistant to the president and chief speechwriter

Nancy Tucker: Cofounding editor, Gay Blade

Gerald Ford

Oliver Sipple: Former marine

Jimmy Carter

Robert Bauman: Congressman (R-MD)

Lou Chibbaro Jr.: Senior reporter, Washington Blade

Margaret Midge Costanza: Special assistant to the president for public liaison

Jon Hinson: Congressman (R-MS)

Bobby Ray Inman: Director, National Security Agency

Jean O’Leary: Co-executive director, National Gay Task Force

Jamie Shoemaker: Cryptologist, National Security Agency

Ronald Reagan

Bill Best: California GOP activist and local television host

Lynden Lynn Francis Bouchey: President, Council for Inter-American Security

Dr. Cesar Caceres: Personal physician of Terry Dolan and Congressman Stewart B. McKinney

Carl Spitz Channell: President, National Endowment for the Preservation of Liberty (NEPL)

John Terrence Terry Dolan: Cofounder and chairman, National Conservative Political Action Committee (NCPAC)

Tony Dolan: Special assistant to the president and chief speechwriter

John Ford: Deputy assistant secretary for agriculture

Peter Hannaford: Advisor to former governor Ronald Reagan

Richard Kind: Proprietor, Friendly Models escort agency

Dr. Frank Lilly: Member, Commission on the HIV Epidemic

Robert Livingston: Congressman (R-LA)

Paul N. Pete McCloskey: Congressman (R-CA)

Stewart B. McKinney: Congressman (R-CT)

Edwin Meese: Counselor to the president (1981–85); attorney general (1985–88)

Franklyn Lyn Nofziger: Press secretary to Governor Reagan; assistant to the president for political affairs

Oliver North: Deputy director for political-military affairs, National Security Council

Martin Price: Publisher, president, and executive editor, Deep Backgrounder

Gerry Studds: Congressman (D-MA)

Leroy Williams: Congressional page

George H. W. Bush

Craig J. Spence: Lobbyist

Pete Williams: Assistant secretary of defense for public affairs

Bill Clinton

Roberta Achtenberg: Assistant secretary of housing and urban development

Bob Hattoy: Associate director, White House Office of Personnel Management

David Mixner: Friend of Bill Clinton; gay activist

COMRADES

Since its establishment by an act of Congress in 1790, Washington, DC, has attracted men and women from every segment of American society. Federalists and Anti-Federalists, Democrats and Republicans, northerners and southerners, easterners and westerners, immigrants and natives, citizens and slaves—all have come to this marble metropolis to join in the perpetual endeavor to form a more perfect union. Included among their number, though scarcely recognized then or now, has been another group of Americans, one whose obscurity was the consequence of their being forced to hide.

What linked them was a sin so vile as to be virtually unspeakable. The early Christian Church condemned these descendants of the biblical Sodom and Gomorrah as those who exchanged natural relations for unnatural. Upon discovering his fellow passengers engaging in dishonorable passions aboard the ship Talbot sailing from London to New England in 1629, Rev. Francis Higginson expressed revulsion for a wickedness not to bee named. In 1837, the state of North Carolina approved a law, copied almost directly from a statute adopted during the reign of King Henry VIII, mandating that anyone who performed the abominable and detestable crime against nature, not to be named among Christians, with either mankind or beast, shall be adjudged guilty of a felony, and shall suffer death without the benefit of clergy. While the threat of capital punishment was lifted in 1869, the taboo against the unsayable abomination remained. In 1927, the New York State Legislature passed a theatrical padlock bill prohibiting any production depicting or dealing with, the subject of sex degeneracy, or sex perversion, and on the West Coast, the Motion Picture Producers and Distributors of America released a list of guidelines banning depictions of profanity, drug trafficking, white slavery, ridicule of the clergy, miscegenation, and any inference of sex perversion onscreen.

Sodomites, perverts, inverts, deviants, degenerates, queers, fairies, fruits, dykes, faggots—gay men and lesbians—these Americans were morally damned, medically pathologized, their very being legally proscribed.* Consequently, the manifestations of their likeness, and the ways they signaled it to one another, had to be disguised, insinuated, and covert. The precise color of an article of clothing, the holding of another’s gaze from across a crowded room, a knowing turn of phrase, an esoteric cultural reference—such were the means by which these men and women communicated the crime of their common existence, and over time, they would develop their own vernacular, rituals, gathering places, and codes of behavior. As Washington grew both in size and significance, they would ineluctably come to populate a secret city, one hidden within the official, open one.

At first, few of those inhabiting this clandestine society understood themselves as members of a community, in the way constituents of more formal polities feel solidarity with others who speak the same language, worship the same god, or live on the same patch of land. For what united these disparate individuals, what connected them to one another as well as to generations past and future, was not a common tongue, religion, or nationality, but something that society condemned, such that what they shared was a status as pariahs. An invisible thread connecting their experiences, one of fear and fixation about same-sex desire, therefore runs through our nation’s history.

The origins of this theme can be traced at least as far back as the country’s War of Independence. Baron Friedrich Wilhelm Ludolf Gerhard Augustin von Steuben was a veteran of the Seven Years’ War and of the exclusively male court of King Frederick the Great of Prussia when Founding Father Benjamin Franklin recruited him to the American revolutionary cause in 1778. Fleeing charges that he had taken familiarities with young men, von Steuben arrived at Valley Forge just sixteen days after a court-martial overseen by Gen. George Washington drummed Lt. Gotthold Frederick Enslin out of the Continental Army for the same crime. Pierre L’Enfant, the French-born architect whom Washington entrusted with designing the new nation’s capital, was a lifelong bachelor described as sensitive in style and dress and as having an artistic and fragile temperament. Though the identity connoted by these euphemisms would not be classified as a social category until the late nineteenth century, the association of sexual and gender nonconformity with moral degeneracy is a political tactic as old as the republic itself. Before Thomas Jefferson and John Adams became great friends and political allies, a newspaper publisher supporting the former accused the latter of possessing a hideous hermaphroditical character, which has neither the force and firmness of a man, nor the gentleness and sensibility of a woman.

Claims of homosexuality have been made upon one of our worst and one of our greatest presidents. The unmarried James Buchanan spent so much time with a fellow bachelor, Alabama senator William Rufus King, that Buchanan’s critics sneered that the two must be lovers. (An academic study published in 2019 argues that they were no more than bosom friends.) The four years that Buchanan’s successor, Abraham Lincoln, spent as a young lawyer sharing a bed with another man, Joshua Speed, the passionate letters they exchanged, and the close relationship Lincoln formed with his presidential bodyguard have led some to conclude that the man whose liberation of others earned him renown as the Great Emancipator repressed his true self.

Lincoln might have been Walt Whitman’s captain, but Peter Doyle was his love. The self-proclaimed bard of Democracy was well into his fifties when he met the twenty-one-year-old horsecar conductor on the Union Line train running along Pennsylvania Avenue one wintry night in 1865. We were familiar at once—I put my hand on his knee—we understood, Doyle recalled of their initial encounter. In a crowded city whose inhabitants frequently shared rooms and often beds, the two men would seek intimacy at a hotel on Washington Avenue after the conclusion of Doyle’s shift.

Rose Cleveland, sister of President Grover Cleveland, performed the functions of first lady until her bachelor brother married two years into his administration. It was not her only unconventional relationship. I cannot find the words to talk about it, Cleveland wrote to divorcée Evangeline Simpson Whipple of the passionate feelings she felt for her, in a disclosure as euphoric as it was apprehensive. The right word will not be spoken. When Whipple married another man, Cleveland was heartbroken, declaring, I will give up all to you if you will try once more to be satisfied with me. Could you not take six months for that experiment? We would go away from everyone. Following the death of Whipple’s second husband, the two women reconnected and rest side by side in an Italian cemetery.

For strapping young lads passing through Progressive Era Washington, DC, the mansion at 2000 G Street shared by Archibald Archie Butt, President William Howard Taft’s military aide, and Francis Millet, a founding member of the U.S. Commission of Fine Arts who helped design the National Mall, was a welcoming retreat. Did you know that the kilt is worn without any drawers? Butt mischieviously wondered in a letter to a friend, marveling at one Scottish lodger’s sartorial habits, or lack thereof. In 1912, Butt and Millet sailed on the RMS Titanic, going down together with the doomed ship. The reason Butt remained a bachelor, a weeping President Taft explained, was because of that love for his mother. In recognition of Butt and Millet being the only U.S. government officials to perish in the maritime disaster, Congress appropriated funds for the construction of a monument in their honor. For over a century, the Butt–Millet Memorial Fountain in President’s Park, south of the White House, has consecrated a relationship whose true nature lies with its dedicatees in a watery grave.

A member of President Warren Harding’s Ohio Gang, Jesse Jess Smith was a supporting player in Teapot Dome, a bribery scandal whose name was a byword for Washington corruption until Watergate surpassed it fifty years later. Smith lived in a house on K Street with his boss, Attorney General Harry Daugherty, described by one chronicler of the era as having had a curious dependence upon the significantly younger Smith, who served Daugherty as a combination of son, secretary, valet, nurse and intimate friend. It was noised about that the men were a couple, but in accordance with the conventions of the day, the press never broached the subject. A snappy dresser who showed no great interest in the girls, Smith often wore a colored handkerchief and matching tie, a coded arrangement used by gay men in the 1920s to signal their shared identity. Aristocratic women greatly valued Smith’s perspective on the cut of a skirt or the choice of a shade, most prominently First Lady Florence Harding, whom Smith regularly accompanied to social occasions. Smith was a walker avant la lettre: a man (usually, and discreetly, homosexual) who escorted the wives of powerful and busy men to parties. In what Henry James, himself a confirmed bachelor, dubbed the city of conversation, walkers fulfilled a vital role.

An insomniac, Smith took regular evening constitutionals around the neighborhood where he and Daugherty lived, just blocks from the White House. If he ever sought company on these nocturnal rounds, he need not have traveled far. At least since the late nineteenth century, men seeking amorous connections with other men did so in Lafayette Square, the seven-acre wooded park directly north of the president’s home. Under the very shadow of the White House, Washington’s chief of police reported with astonishment in 1892, officers had arrested eighteen men "in flagrante delicto. Soon thereafter, the U.S. Army chief of engineers, responsible for the upkeep of federally owned grounds, installed lights around the Washington Monument and other public places in the interest of morality. The diaries of Jeb Alexander, pseudonym of a gay man who lived in Washington during the first half of the twentieth century, provide rich detail about early gay life in the nation’s capital. One August evening in 1920, Alexander happened upon two handsome, clean-looking chaps, refined and cultured, seated near a bronze statue of Baron von Steuben, beneath whose admiring eyes they furtively engaged in a sensual embrace under cover of the dimness."

For those who preferred a degree of privacy the bushes and trees could not afford, the Riggs Turkish baths, located in the basement of the Belasco Theatre abutting the Square, offered alluring possibilities. Featuring a 22,000-gallon pool and sleeping cabins available to rent for the night, the bathhouse was reputed to be the largest and best equipped south of New York. In 1911, complaints from stars, stage managers, and players at the Belasco, owing to the excessive heat on the stage from the baths underneath, forced Riggs to move around the corner, into a building opposite the Treasury Department. Alas, another type of heat sparked more serious trouble. In March 1945, responding to reports of what the Washington Post described as disorderly conduct, officers from the Metropolitan Police Department’s Morals division, or vice squad, raided the baths and arrested some fifty patrons. Men of different nationalities, professions, political commitments, and social standing, they had one thing in common: citizenship in the secret city.

A DOUBLE LIFE WAS POSSIBLE FOR THESE SECRET CITIZENS, provided they exercised a requisite level of vigilance and discretion. Class, race, and sex heavily determined the degree of freedom they could enjoy—wealth, white skin, and manhood being important markers of privilege in a world where everyone was otherwise considered degenerate. As the notion of a homosexual person, as opposed to homosexual acts, was not widely understood until the late nineteenth century, it was unthinkable that these people might constitute a distinct identity group with its own political interests. And so, while the mainstream view held homosexuality to be sick and immoral, during the first four decades of the twentieth century, it was not considered a threat to American society, much less Western civilization.

This perception started to change with the onset of the Second World War, when the federal government began to shoulder the responsibilities of a global superpower. A culture of secrecy descended over the nation’s capital, and with it, an apprehension concerning the guardians of the nation’s secrets. About nobody was this apprehension greater than those who possessed, within themselves, the most damning secret of all. As America instituted a vast bureaucracy for managing sensitive information, a new priority verging on an obsession, national security, imbued homosexuality with existential dangers. America’s global preeminence transformed what had been a private vice into a public obsession as homosexuality assumed an ideological cast and treacherous, world-historical significance. In the hands of journalists and politicians, liberals and conservatives, Democrats and Republicans, presidents and Pullman car porters, the accusation of what one prominent Washingtonian would call an offense too loathsome to mention became the deadliest weapon in the vast arsenal of American political skullduggery.

From the Second World War until the end of the Cold War that followed, the specter of homosexuality haunted Washington. Nothing posed a more potent threat to a political career, or exerted a more fearsome grip on the nation’s collective psyche, than the love expressed between people of the same sex. When America fought fascism, political and cultural leaders associated it with the nation’s Nazi enemies. During the Cold War, voices from across the political spectrum linked it with communism. One of the earliest executive orders signed by President Dwight Eisenhower, a man who played a central role in the struggle against both totalitarian ideologies, prohibited those guilty of sexual perversion from holding any job in the federal government. For most of the twentieth century, the most terrible secret one could possibly possess—more terrible, even at the height of the Cold War, than being a Communist—was being gay.

Secret City is about the wide-ranging influence of homosexuality on the nation’s capital, on the people who dwelled within it, and on the weighty matters of state they conducted. It was an influence attributable to two factors: secrecy and universality. Secrecy is a form of power which can be used inside government, New York senator Daniel Patrick Moynihan observed in a landmark 1997 congressional study. In America’s other major metropolises, New York and Los Angeles, wealth and celebrity, respectively, determine one’s standing. Power is the drug to which Washingtonians have always been addicted, and it is access to secrets that establishes and augments that power. As for universality, the uniqueness of homosexuality as a trait appearing among members of every social group enhanced its spellbinding effect over the capital and the nation. Recalling the controversy over the presence of homosexuals in the federal workforce that consumed Washington in the early 1950s, Stephen Spingarn, an aide to President Harry Truman, observed that they

live in a milieu of their own, a sort of separate world of their own which crosses all sorts of caste and cultural lines, a chauffeur and a Cabinet officer might have a homosexual affair, that sort of thing. In their own world there are no caste lines, and this is useful in espionage organizations because if you happened to know that an important Government official had that weakness, you could infiltrate a handsome young chauffeur …

Everywhere and nowhere, gay men and lesbians were hiding in plain sight. The love that dare not speak its name paradoxically assumed an awesome explanatory power as the motive force in history behind a dizzying array of complex events and phenomena. The decline and fall of ancient Greece and Rome, the collapse of the Hapsburg Empire, the failure of the Treaty of Versailles, the loss of China, the Cuban Revolution, the assassination of John F. Kennedy, the leak of the Pentagon Papers, the Iran-Contra scandal—these were just some of the things that leading Washingtonians attributed to the hidden machinations of this mysterious deviancy.

The secret city was as much a collection of intangible concepts (an all-pervasive sense of suspicion, webs of illusory connections, a catalogue of prejudices) as it was a topography of physical locations (sexual cruising grounds, darkened bars, sites of protest). To protect themselves within Washington’s institutional order, gay men and lesbians were forced to inhabit a combination of the two, a metaphorical space within which their secrets might be safe. Preventing one’s closet from being opened was, for many, a question of life and death. The fear of homosexuality, or even the mere accusation of it, destroyed careers, ended lives, and induced otherwise decent people to betray colleagues and friends. Yet as time wore on, a group of intrepid Washingtonians would emerge from their closets and transform the nation’s capital from a city of witch hunts and recriminations into the front line of a worldwide revolution in consciousness.

The outsized role that homosexuality once occupied in the American imagination makes it a compelling framework through which to undertake a historical reassessment of Washington politics and society during the twentieth century, when a fixation with state secrecy coincided with an increase in visibility for gay men and lesbians. As is so often the case with the subject of historical homosexuality, however, much of the source material needed to tell this story is ambiguous, remains hidden, or has been destroyed. In some cases, it is gay people themselves who are responsible for this erasure, concealing their sexual orientation while they were alive and eliminating any trace of it before their deaths. In others, relatives and historians have done the obscuring. Deciphering the many ways in which homosexuality impacted Washington forced me to search in places other scholars either chose not to look or did not know existed, and to think in ways it may never have occurred to them to think. Most of all, it required that I look carefully, reading between the lines in diaries, letters, memoirs, radio and television reports, congressional hearing transcripts, depositions, and print media accounts. Writing this book often felt like holding up a mirror—one equipped with a special power to reveal once-invisible people, stories, and relationships—to the city I call home and about which I thought I knew so much.

My interest in this subject was piqued by my living in Washington, where every day I walk past the places where the events recounted in these pages occurred, and by my own identity as a gay man. How did people like me, interested in politics and public policy, survive at a time when a core aspect of their very being was considered a mortal danger to the country? What sort of choices and sacrifices did they confront? Whom could they trust? Surveying the vast literature of American political history, it became apparent how often gay people and issues have been consigned to footnotes—that is, when not expunged from the historical record altogether. Because homosexuality was (and, in some quarters, lamentably remains) a subject considered indecent if not immoral, many of the historians and institutions that have shaped our understanding of the American past have neglected to explore whole swaths of it. Due in large part to this stigma, the study of gay people and topics in history has largely been taken up by gay people themselves. Homosexuality not being a heritable trait, however, the preservation of this history lacks the natural means of continuity available to other minority groups. Stories of gay struggle and accomplishment are not passed down over dinner tables or through family heirlooms; rarely are they taught in schools. This knowledge deficit harms not only gay people, deprived of a common past and a way of understanding their place in the world, but all Americans, whose awareness of their country’s history is made poorer by the large parts left unexplored.

By documenting the evolution of American politics and government secrecy through the lives of people compelled to keep a core part of themselves hidden, I hope to offer a new interpretation of our country’s past. The tendency to view gay history as a subject separate and distinct from American history has always struck me as erroneous and constrictive. Since conceiving the idea for Secret City over a decade ago, my overriding ambition has been to integrate these two histories, to weave the invisible and visible threads together into a coherent whole, to put the central events, influential ideas, and prominent figures of an era into greater context by opening the many little (and several not-so-little) closet doors behind which so much has been secreted away. Though their stories may sometimes be hard to find, gay people have always been here, shaping the country at every level, from the lowliest of clerks to the loftiest of White House aides. In illuminating the lives of these men and women, it is my hope that this book will help them attain the place they have long been denied yet belatedly deserve in the history of the great experiment that is America.

FRANKLIN DELANO ROOSEVELT

I HEAR it was charged against me that I sought to destroy institutions;

But really I am neither for nor against institutions,

(What indeed have I in common with them—or what with the destruction of them?)

Only I will establish in the Mannahatta, and in every city of these States, inland and seaboard,

And in the fields and woods, and above every keel little or large that dents the water,

Without edifices, or rules, or trustees, or any argument,

The institution of the dear love of comrades.

—Walt Whitman, I Hear It Was Charged Against Me

1

NO COMMENT

Sumner Welles had a secret.

It was a secret that, in 1940, the forty-seven-year-old undersecretary of state had in common with thousands of other men and women across Washington, DC, a swampy southern town not yet capital of the free world—a secret that bound him to earlier generations and linked him with those not yet born. Once discovered, it was a secret that could lead to societal banishment, institutionalization, professional disrepute, and criminal prosecution. In certain parts of the country, at a certain hour of the night, this secret might elicit horrific violence or even murder. And in Welles’s case, it was a secret that would set off a perilous chain of events leading to the destruction of his career, the wrecking of his marriage, and the hastening of his death, and that would, for more than half a century, leave myriad innocent victims in its wake.

By all external indicators, however, Welles had achieved nearly everything that a man of his status and vocation could have wished for. The progeny of New England blue bloods, Welles was named for his great-uncle, the abolitionist senator Charles Sumner, and he enjoyed wealth, power, and renown. As a boy of twelve, he carried the bridal train of his Groton roommate’s sister, Eleanor Roosevelt, at the wedding to her cousin Franklin. Following the same academic path as the future president he would eventually serve, Welles enrolled at Harvard, where he studied Spanish culture and history and graduated after three years. His rapid ascent up the gilded ladder of American diplomacy was guaranteed the day he scored higher than any other applicant on the Foreign Service exam, and his appointment as head of the State Department’s Latin American Affairs division at the age of twenty-eight made him the youngest person ever selected to lead a regional bureau.

In 1925, Welles left his first wife for Mathilde Townsend, heiress to a railroad and coal fortune and a ravishing beauty as well known in Paris, Philadelphia and Newport as she was in the nation’s capital. Townsend had herself been married to Sen. Peter Gerry of Rhode Island, a friend of President Calvin Coolidge. Though this was an era when the private affairs of wealthy and powerful men did not generally intrude upon their public careers, to cuckold a U.S. senator, and a close associate of the president’s, no less, crossed a line. It was widely rumored that Coolidge personally ordered Welles’s dismissal from the State Department as revenge.

Welles and Townsend lived luxuriantly in a French Renaissance–style mansion at the corner of Massachusetts and Florida Avenues, where they were waited upon by fifteen servants. When his old family friend Franklin Delano Roosevelt won the presidency in 1932, Welles was assured a senior State Department job, and after FDR appointed him ambassador to Cuba the following year, the New York Times heralded Welles as the most-talked-of diplomat in the service of the United States. Elevated to undersecretary in 1937, he helped craft the administration’s Good Neighbor policy, which sought to redress the legacy of American imperialism in the Western Hemisphere through assurances of military neutrality and reciprocal trade agreements, and authored the eponymous Welles Declaration pledging nonrecognition of the Soviet Union’s brutal occupation of the three Baltic states.

FDR would have certainly chosen Welles to be secretary of state had he not been compelled to appoint the lethargic and sickly Tennessee senator Cordell Hull to placate the southern wing of his New Deal coalition. A curmudgeon with false teeth, Hull was an odd fit for the State Department, then the bastion of worldly, well-cultivated men with sophistication and class—men, in other words, like Welles, who never walked from the State Department to the Metropolitan Club without his Malacca cane, and [who] in the summer wore an impeccable Panama hat, as one of his administration colleagues fondly recalled. FDR’s practice of dispatching personal envoys like Welles to carry out important diplomatic missions rankled Hull, who may have been genetically predisposed to holding a grudge. According to legend, Hull’s father, returning home from the Civil War battlefront, got into a fight with a man who threw him into a river. Three decades later, Hull Sr. tracked the scoundrel all the way down to Alabama and shot him on his front porch.

Welles regularly found himself in the position of acting secretary due to the recurrent illness of his nominal superior, who frequently skipped cabinet meetings and, at those he did attend, often fell asleep. If Welles was present in Hull’s stead, and the president asked him a question, the reply would be swift, precise, and comprehensive, wrote journalist John Gunther. FDR must have wished at least ten thousand times that Welles, not Hull, was the actual Secretary.

While FDR could always depend on him for candid assessments of the geopolitical situation, Welles was the soul of discretion. Just to look at him can tell that the world would dissolve into its component parts if only a portion of the weighty state secrets that he carries about were divulged, Interior Secretary Harold Ickes recalled. Future secretary of state Dean Acheson, who was one year behind Welles at Groton and who worked under him in the State Department, described Welles as not an easy man to know, citing a manner formal to the point of stiffness. British prime minister Winston Churchill credited Welles with coining a phrase since uttered perhaps more than any other in Washington: No comment.

Ironically, it was a secret that would be Welles’s undoing.

On September 17, 1940, standing in for his titular boss, Welles accompanied the president, most of the cabinet, and some one hundred members of Congress at the funeral of former Speaker of the House William Bankhead in Jasper, Alabama. Aboard the presidential train back to Washington that night, Welles joined FDR’s vice presidential running mate Henry Wallace and several administration officials in the dining car, where he began to drink heavily. The men eventually retired to their private cabins. What happened next would assume near-mythic proportions.

At around 5 a.m., Welles pressed a buzzer, alerting the porters in the adjoining carriage. Alexander Dickson, a twenty-nine-year veteran of the Pullman Company, who had staffed the presidential train since the Harding administration, answered the call. Like every other porter, Dickson was African American.

Come in, porter, Welles ordered. Close and lock the door.

Dickson hesitated.

It will be alright, Welles insisted.

Moments later, Dickson fled in distress. You have a cocksucker up there in Compartment E, he told his colleague Samuel Mitchell. He wanted to blow my whistle.

Welles rang the buzzer again. This time Mitchell answered. Welles, shirtless and in his pajama pants, instructed Mitchell to close the door and asked if he wanted to make twenty dollars.

I don’t quite understand what you mean, Mitchell replied.

Welles kept repeating twenty dollars.

No, sir, you have the wrong man, Mitchell stated firmly, leaving Welles alone.

For two hours, Welles persisted in his propositions. At one point, a porter named John Stone volunteered to answer Welles’s call, telling his colleagues that he knew how to handle that type of man. After Stone entered his compartment, Welles slipped behind him, loosened his bowtie, unbuttoned his coat, and instructed Stone to take off the rest of his clothes and get on the bed.

You know what you are in here for, don’t you? Welles asked, his speech slurred by drink.

To bring you coffee? Stone answered.

Welles unfurled a roll of dollar bills. I will give you $20, $50, or even $100; money makes no difference to me. Stone absconded.

Ten days after his return from Alabama, Welles traveled alone by train to Cleveland for a speaking engagement, again drunkenly propositioning a series of porters. You turned down $50 to suck a nice, clean dick? one of the men facetiously asked a colleague. The porter replied that he wouldn’t accept a sum as great as $5,000 to perform such an act as you have to work three years to become a carpenter or a bricklayer but it takes only one suck to make a cocksucker.

Word of Welles’s escapades wormed its way back to Washington, consumed by debate over how the country should respond, if at all, to the growing fascist menace in Europe. Senators Burton K. Wheeler of Montana and Henrik Shipstead of Minnesota, strong opponents of FDR’s policies to supply military aid to the beleaguered British, got wind of the charges and tried to persuade Washington Times-Herald publisher Eleanor Josephine Medill Cissy Patterson to expose him. One of Washington’s premier Cave Dwellers, as the coterie of fabulously wealthy families native to the city was known, Patterson lived in a thirty-room marble mansion on Dupont Circle. A vociferous opponent of the New Deal, she regularly published vitriolic front-page editorials excoriating the Roosevelt administration. Patterson felt a deep, personal loathing for the president, and the feeling was fully reciprocated. Regardless, the story about the undersecretary and the African American train porters was simply too prurient to print. The sexual habits of influential men, even morally degenerate ones whose peccadilloes transgressed the color barrier, were off-limits.

Another factor Welles had going in his favor was his assiduous cultivation of journalists—one scribe in particular. Drew Pearson began writing his nationally syndicated column, the Washington Merry-Go-Round, in 1932 for his former mother-in-law Cissy Patterson’s paper. Working on a grueling daily deadline, the mustachioed and fedora-sporting Pearson provided his millions of readers across the country with a regular supply of juicy exclusives about the wheeling and dealing in the nation’s capital. Pearson’s prim and proper Quaker demeanor belied a professional ruthlessness, and the title of his column, evoking innocent memories of childhood frolic, disguised a transactional endeavor that rewarded Pearson’s allies and punished his enemies. As a source, Welles qualified as an ally, which by extension made Hull an enemy. Thanks to information supplied by Welles, the secretary of state was a frequent target of the Washington Merry-Go-Round—such as the time Pearson reported that Hull and his croquet clique (named for the group of State Department career boys who played the lawn game every night) nearly pushed through a one-hundred-million-dollar loan to Spanish dictator Francisco Franco only to be stymied at the last minute when Welles protested directly to FDR. Hull learned to work the media as well, and when negative stories appeared in the papers about Welles, it did not require much intuition for the undersecretary to trace them back to his aggrieved boss.

There was another diplomat whom Welles suspected of trying to undermine him in the press, however, one whose privileged upbringing, aristocratic bearing, and, quite possibly, secret life closely resembled his own.

William Christian Bullitt was destined to rival Sumner Welles. The scion of a prominent Philadelphia family, Bullitt was the grandson of one of America’s ten wealthiest men and distantly related to George Washington, Patrick Henry, and Pocahontas. Voted Most Brilliant member of the Yale class of 1912, Bullitt became Washington bureau chief for the Philadelphia Public Ledger, where he developed such a talent for extracting information that rival reporters hired a private detective to tail him around the city. Bullitt’s work as a roving European correspondent in the early years of World War I caught the eye of President Woodrow Wilson’s State Department, which recruited him as an expert on the Central Powers and Russia’s revolutionary movements.

Bullitt worked three doors down the hall from Assistant Secretary of the Navy Franklin Delano Roosevelt in the grand, French Second Empire–style building located directly next to the White House that was then home to the Departments of State, War, and the Navy. After the signing of the Armistice, Bullitt accompanied President Wilson to the Paris Peace Conference, the first international summit where modern tools of espionage, such as electronic bugging, were used. There, the twenty-seven-year-old novice diplomat headed the American delegation’s Division of Current Intelligence Summaries, in which capacity he compiled a daily brief on European political developments and began to acquire a lifelong obsession with secrecy.

In March 1919, Wilson sent Bullitt on a clandestine mission to Moscow, by then under Bolshevik rule, to negotiate the removal of Allied troops deployed to Russia during its civil war. Traveling with the journalist Lincoln Steffens, Bullitt wrangled an audience with Soviet foreign minister Georgy Chicherin and Chief Commissar Vladimir Lenin, who praised the envoy as a young man of great heart, integrity and courage. The admiration was mutual. Repeatedly declaring to Steffens, We have seen the future, and it works! (a quotation Steffens was to appropriate and popularize), Bullitt returned to Paris with a proposal from the Bolsheviks and admiration for their achievements. Allied leaders rejected as too lenient the peace terms Bullitt had negotiated, however, leading him to resign and angrily declare that he would go to the Riviera, lie in the sand and watch the world go to hell. Bullitt felt especially bitter toward Wilson, who had sent him to Moscow only to sideline him afterward. He exacted revenge by testifying before the U.S. Senate against Wilson’s signal foreign policy accomplishment, the Treaty of Versailles, delivering a coruscating speech that was widely credited with persuading the body to reject the compact. Breaking so publicly with Wilson put Bullitt on the outs with the Democratic Party foreign policy elite, and his diplomatic career appeared to be finished. For his public turn against the president he had once served, he was denounced as a tattler and violator of confidence.

In 1923, Bullitt returned to Paris, where he joined the burgeoning community of American expatriates. He met and eventually married one of its brightest stars, the radical journalist Louise Bryant, widow of the Communist activist and writer John Reed. Bullitt revered Reed, author of the classic firsthand chronicle of the Russian Revolution, Ten Days That Shook the World. Returning to his literary roots, Bullitt published a roman à clef of Philadelphia manners and high society, It’s Not Done, which sold more than one hundred fifty thousand copies. (The Great Gatsby, published the previous year, sold some twenty thousand.) He also wrote a play castigating his former boss, The Tragedy of Woodrow Wilson, which was never produced. When Bullitt’s relationship with Bryant came under strain (allegedly due to impotence), he contacted a neurologist he had met in Vienna named Sigmund Freud. Bullitt developed such a close relationship with Freud that he was one of only three people whom the founder of psychoanalysis permitted to address him by his given name rather than the formal Herr Doktor.

Based upon extensive correspondence between the two men, one of Bullitt’s biographers speculates that the course of therapy Bullitt underwent with Freud may have centered on his sublimation of homoerotic desire for Reed, which manifested itself in his marriage to Reed’s widow. Bullitt was tormented by homosexuality in other ways. When he discovered that Bryant was having an affair with the English painter and sculptor Gwen Le Gallienne, he sued for divorce and requested full custody of their daughter, so that she would no longer be exposed to Bryant’s perversity. At the divorce proceedings in Philadelphia, heard before Bullitt’s friend, Judge Francis Biddle, Bullitt described with horror the time Bryant took him to a party of homosexuals; he insisted they leave at once. Bullitt would express his revulsion for homosexuality more enduringly in a book he coauthored with Freud. The psychoanalyst and his patient had bonded unexpectedly over their mutual disdain for Woodrow Wilson, whom Freud blamed for the breakup of the Austro-Hungarian Empire and Bullitt for ruining his diplomatic career. Meeting in the evening hours at Freud’s Vienna home, the pair hashed out a thesis as to why Wilson’s presidency had been a failure. You and I know that Wilson was a passive homosexual but we won’t dare say it, Freud mischievously told Bullitt.

Certainly we’ll say it but subtly, Bullitt replied.

That’s the equivalent of not saying it at all.

Bullitt and Freud pursued their collaboration intermittently into the latter half of the 1930s, picking up in earnest after Bullitt, by then ambassador to France, spent tens of thousands of dollars of his own money to purchase passage to Paris for Freud and his family following the Nazi Anschluss of Austria. A series of editorial disagreements between the coauthors, Bullitt’s political ambitions, and deference to Wilson’s widow perpetually delayed publication of the book, however, and it was not released until 1967, nearly three decades after Freud’s death. Thomas Woodrow Wilson: A Psychological Study qualifies as one of the strangest literary collaborations of the twentieth century, a psychobiography alleging the twenty-eighth president to have been a repressed homosexual ruled by Oedipal forces. Bullitt and Freud located Wilson’s political flaws in a femininity born from hatred of his father, which led him to seek an affectionate relationship with younger and physically smaller men, preferably blond. At Versailles, the pair wrote, Wilson met the leaders of the Allies not with the weapons of masculinity but with the weapons of femininity: appeals, supplications, concessions, submissions. Long before armchair psychoanalysis of a sitting president became a collective national pastime, Bullitt and Freud developed a theory attributing the destabilization of interwar Europe to a former president’s latent homosexual neuroses.

Like Sumner Welles, Bullitt was called back into government service after his friend FDR’s election, as special assistant to Cordell Hull. The fixation with secrecy bordering on paranoia that he acquired as a young aide at Versailles had only grown more intense. At an economic conference in London, Bullitt insisted that American officials sweep all the walls, ceilings, and floors of his hotel room for recording devices—years before such precautions became standard practice for American diplomats traveling abroad. Meeting with the American ambassador at the U.S. embassy, Bullitt suddenly sprang up from his chair and drew back the curtain, searching vainly for a hidden microphone. When FDR established diplomatic relations with the Soviet Union, Bullitt was the obvious choice to serve as America’s first ambassador to the revolutionary state. Immediately upon arriving in Moscow in 1934, he visited the Kremlin to pay tribute to his hero John Reed, whom the Bolsheviks had buried within the building’s exterior wall. Unbefitting an admirer of the Bolshevik cause, Bullitt had a Cadillac V-12 limousine and two Pontiacs shipped to Russia at his own expense, and he requisitioned a grand prewar mansion as his ambassadorial residence. Under Bullitt’s orchestration, Spaso House became the city’s hottest social destination, once the scene of a party so lavish—replete with a Czech jazz band, baby goats, a drunken bear, and a replica of a collective farm—that Mikhail Bulgakov immortalized it in his novel The Master and Margarita. The best party in Moscow since the revolution, Bullitt bragged in a cable to FDR.

Outside the embassy walls, however, the atmosphere was darkening as Soviet leader Joseph Stalin unleashed his reign of terror. Bullitt’s already heightened sense of suspicion increased with each and every friend or acquaintance who disappeared in the purges. One night over dinner with his staff, Bullitt felt an unusually acute sense of unease. Looking around the table at the men and their Soviet-born wives, he imagined himself at the League of Nations, that ill-fated attempt at world government he had opposed in his testimony before the Senate. The increasingly brutal and unpredictable actions of his Soviet hosts, combined with a fear that Soviet women were filching information from his embassy, prompted Bullitt to recommend an executive order forbidding Foreign Service officers from marrying foreigners without express permission from the secretary of state. In an article about the regulation, the Chicago Daily Tribune described its mastermind as a man whose capacity for suspicion is highly developed.

Bullitt’s obsessive interest in the personal lives of his employees contrasted sharply with his public persona as a bon vivant. Ever since resumption of diplomatic relations with Russia … our Embassy there has had a questionable reputation, a U.S. government official reported back to his superiors in 1943, long after Bullitt had left. I have visited every American Mission in Europe, the Near East, and the Americas and at almost every post when Moscow is mentioned the discussion turns to morals. The American legation, he elaborated, had thoroughly absorbed the values of the Soviet capital, regarded as the city of ‘free love.’ Though the report cited instances of mostly heterosexual debauchery (including a claim that the Lend-Lease program headquarters was the scene of wild orgies in which Gen. Omar Bradley, later to become chairman of the Joint Chiefs of Staff, participated), Embassy Moscow was also apparently home to more than its fair share of sexual deviants. Edward R. Pierce, who worked as a clerk at the embassy during Bullitt’s tenure, complained about a lot of fake marriages among his colleagues. Bullitt, he recalled, brought with him a weird bunch … straight off the Left Bank in Paris, and by the time Bullitt departed Moscow in 1936, Pierce claimed that a full third of the embassy staff was gay. When the mission was evacuated in 1941 after the German invasion of the Soviet Union, a Russian employee referred to the caravan of clerks traveling from Moscow to Vladivostok as the pansy train.

Notwithstanding the accuracy of Pierce’s estimation, the early twentieth-century U.S. Foreign Service was a uniquely attractive institution for gay men, affording them a measure of freedom and a literal world of possibilities unavailable at home. First and foremost, it offered a respectable career path for confirmed bachelors, long tours overseas obviating uncomfortable questions about the lack of a wife and family. Postings in exotic lands with more relaxed attitudes toward homosexuality also provided an escape from the repressive mores of American society. Finally, the Foreign Service was almost exclusively male. Raymond Geist, a consular official posted to Germany during the rise of the Third Reich, demonstrated how a gay man could serve as a diplomat under even the riskiest of circumstances. By day, Geist attended meetings with senior officials of a regime that herded homosexuals into concentration camps. By night, he shared his bed with a German man. Alexander Comstock Kirk, described by Life magazine in 1945 as probably the outstanding career diplomat now functioning for the U.S. State Department, was a more prominent example. Heir to a Chicago soap fortune and a graduate of Yale (where he overlapped with Bullitt), Harvard Law School, and Paris’s elite Sciences Po, the eccentric Kirk had a long and distinguished career. Serving at the American embassies in Moscow, Berlin, and Rome, all during periods of high diplomatic tension when Washington had withdrawn its ambassador, Kirk, a dandyish dresser who wore lavender silk tuxedos, liked to boast that he was a continual poke in the eye to hostile foreign governments. This ability to perform in a series of hardship posts with distinction might explain Kirk’s attitude toward his gayness, which he apparently did little to conceal. A Federal Bureau of Investigation report noted that he was commonly regarded as a homosexual, and a U.S. government official claimed that one of the reasons he entertained so lavishly was in order to buy everyone out so that no one reports his abnormal personal conduct.

With his patrician pedigree and white, Anglo-Saxon, Protestant heritage, Kirk personified the U.S. Foreign Service, which well into the twentieth century dissuaded men lacking private incomes from even applying to join its privileged ranks. They possessed a common background, common experience, and a common liking for old wines, proper English, and Savile Row clothing, the historian Waldo Heinrichs wrote of America’s prewar diplomatic generation. Indeed the Diplomatic Service most nearly resembled a club. The sexually unorthodox Kirk embodied the Foreign Service in another way, one likelier to raise eyebrows back home. Ruminating upon the State Department of the 1930s, it was with worldly sophisticates like Kirk in mind that one prominent historian would later ridicule it as an institution that Americans … reasonably regarded as a refuge for effete and conventional men who adored countesses, pushed cookies and wore handkerchiefs in their sleeves.

It was in search of the freedom this club offered to men like him that an ambitious son of poor Italian immigrants arrived at the gates of the U.S. embassy in Moscow on June 11, 1934. Bullitt had already exhausted two clerks when, just a few months into his stint as ambassador, he desperately cabled Washington: Please send a secretary who can stand Moscow and me. Washington sent Carmel Offie.

Born and raised in the coalfields of Pennsylvania, Offie was a product of public schools and Cambria-Rowe Business College. This alone made him an oddity among his fellow Foreign Service officers: some three-quarters of those he served alongside in Europe had attended prestigious prep schools like Groton or St. Paul’s, and of those, two-thirds had graduated from Harvard, Yale, Princeton, or one of a handful of elite foreign universities. But Offie’s excellent transcription skills—He had a mind, you know, almost like a tape recorder, one colleague recalled, enabling him to type two hundred words a minute—landed him a job with the American ambassador to Honduras, in 1931, at the age of twenty-two. Diminutive, by all accounts physically unattractive, and homosexual, Offie made up for these traits that lay beyond his control by honing a set of those he could master: charm, wit, and unflagging loyalty to his superiors. Offie’s remarkable rise was evidence of his absorbing a lesson that the most successful gay Washingtonians of his generation, working across all branches of the government, learned early: to ensure your survival, become indispensable to those with power.

In Moscow, Offie made himself essential to Bullitt, taking dictation, running errands, and always available for a relaxing game of chess. This wretched young man puts up with being at his beck and call all day and all night, for if [Bullitt] has an idea during the night he calls for his attaché to take down the draft, a British diplomat in Moscow remarked of the relationship between the American ambassador and his devoted assistant. Bullitt gets up in the morning at any hour between five and seven and takes the unfortunate fellow for a walk with him. In 1935, Offie accompanied Bullitt on an expedition to Tokyo, where Bullitt hoped to gather intelligence for FDR on Japanese regional ambitions and the insurgency on the Chinese mainland led by the Communist leader Mao Zedong. When Mr. Offie reached Moscow he lacked social polish and his eagerness and self-assurance often produced an appearance of ‘freshness,’ Bullitt wrote the president in a report about their voyage. However, in the course of our trip around the world he acquired the social poise he conspicuously lacked, and his ‘freshness’ is rapidly disappearing. Other colleagues noticed Offie’s multifarious talents. A young Foreign Service officer at the Moscow embassy named George Kennan described him as "a renaissance type; earthy, extroverted, enormous energy, endless joie de vivre; a born ‘operator.’"

When Bullitt assumed the ambassadorship to France in the fall of 1936, Offie followed. Every day at 4 a.m., the dutiful aide accompanied the embassy chef for his rounds at the Paris market stalls, helping him gather comestibles for that evening’s soirée. (Bullitt earned the sobriquet Champagne Ambassador for his extravagant fêtes; at one party, 600 guests collectively finished off 490 bottles of Pommery 1928.) In addition to stocking the embassy pantry, Offie would occasionally acquire specialty perfumes and foie gras to send via diplomatic pouch to Marguerite Missy LeHand, FDR’s private secretary, with whom Bullitt had initiated a romance years earlier before departing for Moscow. Keen to keep his boss in FDR’s good graces, Offie wrote LeHand asking her to inform the president that Bullitt was extremely popular here and is doing a swell job, but in order to live up to his reputation he is kept constantly on the go from fourteen to eighteen hours a day, and it’s too much. Buttering up Bullitt to the White House also paid dividends for Offie, tales of whose social poise (and social climbing) became a regular feature of Bullitt’s witty and informative dispatches to the White House. Regularly corresponding with the president by transatlantic telephone or telegram, Bullitt displayed a phenomenal ear for gossip, a gimlet eye for detail, and an extensive assortment of connections across the Continent, his communiqués constituting what Janet Flanner, longtime Paris correspondent of the New Yorker, described as a kind of extraordinary private European gazette; what interests him is the news behind the news. (FDR’s nickname for Bullitt, Bill Buddha, was as much a nod toward his oracular assessments of the international scene as it was a jibe at his bald head.) Missy LeHand lauded Bullitt’s series of cables as a confidential dispatch which reads like a most exciting novel, one in which Offie played a delightfully charming supporting role. In one telegram, Bullitt reported that Offie had become the preferred bridge partner of the Duchess of Windsor. In another, Bullitt told the president that the lover of the French politician Paul Reynaud

summons [Offie] to her love nest almost daily; and he keeps her within reasonable bounds. I have less patience than he with lack of character so that more than ever, Offie is the power behind the throne … A few days ago, the Comtesse de Portes said to him that if the American Embassy had any difficulty with any department of the French Government or the French Army, he had only to let her know and the matter would be settled to our satisfaction at once. He tried it once and it worked!

When the twenty-year-old son of the American ambassador to Britain and his best friend, gallivanting about Europe in the summer of 1937, needed a place to stay on the Paris leg of their journey, Bullitt deputized Offie to look after the two collegians. John F. Kennedy had met Kirk LeMoyne Lem Billings at Choate, the tony Connecticut prep school. The boys immediately took a liking to each other, bonding over their common distaste for the institution’s austere conditions and regimental ways. Billings, however, hoped there might be something more to the relationship than a shared spirit of teenage rebellion against authority, and at seventeen had expressed his sexual interest in the future president of the United States by sending him a bit of coded doggerel jotted onto a scrap of toilet paper. For the hormonal adolescents at Choate, communicating forbidden desires on bathroom tissue—easy to swallow or dispose of—was one of many traditions inherited from British boarding schools. Please don’t write to me on toilet paper anymore, Kennedy firmly responded. I’m not that kind of boy.

Though Kennedy might not have been that kind of boy, the depth of his platonic relationship with Billings foreshadowed how remarkably relaxed he would be around those who were. Unusual for the time, Billings’s frank acknowledgment of his same-sex desires did not engender feelings of disgust or anger in the young man to whom they were addressed. On the contrary, it strengthened their friendship. Kennedy’s father, Joseph Kennedy Sr., would refer to Billings as a second son, a status that the intensely tribal family patriarch conferred upon no one outside the Kennedy clan.

When Bullitt told his counterpart in London that he had assigned Offie the task of accommodating Jack and Lem, the elder Kennedy knew they would be in good hands. Kennedy Sr. had had frequent dealings with Bullitt’s aide-de-camp, sometimes calling him up to four times a day, and once even tried to hire him away as his own personal assistant. Upon the boys’ arrival in Paris, Offie pulled out all the stops, ensuring that they were comfortable at the ambassadorial residence and attending to their every