Meet Harry Allen, transgender at-risk youth of yesteryear

Allen was a media favorite in his day.

Mossback's Northwest host Knute Berger tells us why Harry Allen was a different sort of outlaw.

This story has been updated to correct gender references in the original article, which was published in 2014.

He was a young man in his early 20s who lived by his wits. He could fight, and looked great in a suit, tie and derby. He smoked, drank and ran with a rough crowd. He was reputedly close to the city's gang leaders and very familiar with the insides of a jail cell, having spent time there for theft, vagrancy, selling liquor to the Indians, resisting arrest and other offenses. He was jugged once in Portland for violating the Mann Act by allegedly transporting a woman over a state line for immoral purposes. The woman was his partner, a Seattle prostitute who "posed" as his wife.

Meet Harry Allen, or sometimes Harry Livingston, a troublemaker with a tough background, a penchant for getting attention and an identity that caused confusion among and conflict with his contemporaries.

Nowadays, we'd likely see Harry as an at-risk transgender youth. At the time he was most often written about in many newspaper accounts with his given name and gender, Nell Pickerell. Digging into his history is to find a person who feels utterly contemporary, whose life, more than 100 years later, parallels the experience of Seattle street kids today. He was born in an era that didn’t know what to make of him, or what to do with him.

Harry Allen was born in 1882 and given the name Nell Pickerell. A news account in the Seattle Mail and Herald described his father as a drunkard and a wife beater. From childhood on, he mostly identified as male, often working at "men's" jobs (bartender, cowboy, farmhand) in men’s clothing. 

He became pregnant at age 16. The father of his baby was rumored to be a much older man who skipped town. Harry’s son was raised by his mother, who told the boy that Harry was his uncle.

By his late teens Harry was living in Tunnel City, the rough and tumble Cascade boomtown that sprouted up during the digging of the Great Northern railroad tunnel at Stevens Pass. An article in the St. Paul, Minnesota, Globe in 1900 called Tunnel City the "wickedest place on earth" where "scum of the earth" got drunk on payday and indulged in every vice known to man in a "fight club" atmosphere. The story mentions only one woman: "... a fight is usually arranged between two women. Sometimes there is a coarse love story at the bottom of these fights. ... One of the women favored male attire. She is a handsome girl, Nell Pickerel[l] by name, whose respectable parents live in this city. She is only eighteen years of age, but incorrigible. The ambition of her life is to act like a man."

That was a bold move in the 19th and early 20th centuries. Many frontier women did it for practical reasons, such as to avoid being molested in a frontier dominated by men. (In the Northwest of Allen's era, the male-to-female ratio was around 14 to 1.) Others sometimes dressed as men for work or because it was more sensible to shed their Victorian finery when crossing the Rockies in winter. Dressing as a man to enjoy a more liberated lifestyle was looked down on, though not unknown. Think Calamity Jane.

But there were also women who lived in quiet disguise for years. Washington State University historian Peter Boag, whose 2011 book Re-dressing America's Frontier Past documents this fascinating subject, says cross-dressing women were a "ubiquitous presence in the West."

Even so, Harry was something else, a person recognized by most of society as a woman, but who identified completely as a man. At first, the newspapers seemed almost charmed by him; he certainly made great police blotter copy. A 1901 Seattle Times story describes how he looked down at the police station one morning after he’d been arrested for theft: "Dainty patent leathers adorned her feet. She wore a colored shirt, stand-up collar, bright red tie. Her jet black hair was cut short and parted in the middle. Her well rounded cheeks were tinted with the glow of health. Her eyes were bright and clear. She carried herself erect and well. She made a most handsome boy."

Despite the refusal of authorities to recognize him as such, Harry lived publicly as a man, a fact that landed him in a lot of trouble. It was one thing to be seen as a woman wearing a man's "natty" coat and tie; it was quite another to be "seducing" women while wearing that attire.

Seduction, in fact, was a crime in Washington, which usually targeted men who slept with women. The penalty was five years in prison, or three years of forced marriage. Many men opted to “do the right thing” rather than bust rocks at the state pen in Walla Walla. But no one knew quite what to make of Harry’s affairs.

The newspapers of the era are full of stories about Harry ruining lives with his perceived deception. Lovers were said to have committed or attempted suicide upon discovering that he was transgender. After coming to Seattle to be with Harry, Dolly Quappe, a pretty blond waitress from Portland, drank carbolic acid and died the day after Christmas 1901. It is unclear whether Dolly was upset about Harry's anatomy or simply jealous. She allegedly suspected Harry of wooing another.

In 1903, a "handsome brunette" named Pearl Waldron reportedly attempted suicide by shooting herself in the chest in Denny Park after declaring her love for Harry. These stories and others were denied or explained away by Harry, but they made him notorious nonetheless. Lock up your daughters, Harry's coming to town!

If the newspapers enjoyed reporting Harry’s antics, they loved morality tales about fallen women even more. At a time when the roaring frontier boomtown of Seattle was bumping into the era of progressive reform, such tales were used as evidence that the city needed to get a handle on vice. 

"[W]hile probably not guilty of murder, [Allen] is at least responsible in a sense for the loves of these two young [suicidal] women,” railed the progressive Seattle Republican in 1903. “And it is quite time there was some steps taken to suppress this seemingly consciousless [sic] individual, with perverted ideas."

Suppress they tried.

From a stroll through newspaper clippings between 1900 and 1922, it seems clear that local police picked on Harry. In the glory days of Seattle's red-light districts, gambling and police corruption, he was a target. But he courted trouble, too.

For example, Edward "Black Jack" Morse, a desperado recently arrived in town from the Nome, Alaska, gold fields in 1900, was rumored to be an associate of Harry’s, perhaps a lover. When Morse died in a shootout with Seattle police — his gang attempted to rob a Chinese business — a picture of him and Harry was reportedly found in his pocket. "At the time the photo was taken,” wrote The Seattle Star, “Nell Pickerell, who prefers to be called Harry Livingston, was acting as a bartender in a North Seattle saloon and was living with Morse." That kind of press gave Harry an outlaw aura.

Things would change for Harry in later years when he allegedly became a paid police informant, snitching on the city's bootleggers after the state went "dry" in 1916. But as a young man he drifted in and out of prison. (In at least one case, his mother went down to the station to get her son released on the promise that Harry would leave town.)

Harry was arrested in Tacoma, Yakima and Ritzville, often merely for dressing as a male, and was considered undesirable, a vagrant. He fought with police, frequented saloons (illegal for unescorted women) and consorted with prostitutes. He was even busted for reckless bike riding. He was a perpetual suspect who became known throughout the region.

Harry’s arrests and wanderings were not at all unusual. From the 1890s through the 1920s, the Pacific Northwest was awash in migrant workers, runaways and other transients like Harry. Many rode the rails that were being laid and opening the region to easier access from the rest of the country. These so-called hobos, bums, yeggs and tramps drifted from city to city, mingling with other working class folk, and living in what was called "Hobohemia," a kind of floating world of transients.

In Seattle, people gathered by the thousands. They came for the same reasons most people do today: jobs. The Northwest had them in abundance: fishing, mining, logging, railroad construction, fruit packing and picking. Seattle was a big port that needed sailors and dock workers. Historian Boag calls the time period following the 1893 depression "the golden years" of the casual worker.

The Klondike gold rush beckoned, but many left the digs for Seattle, disappointed and looking for work in the city that launched their fevered, strike-it-rich dreams. Some wound up stranded and broke after losing their last dollars in Seattle's dives and gambling dens. If Seattle was the gateway to the gold rush, it was also a catch basin for failure. Booming Seattle’s prosperity was accompanied by a growing population of urban poor, many of them unmoored young people who were ripe for exploitation.

Seattle became known as a national "headquarters" for white slavery and the civic apparatus thrived on it. Prostitutes, many of them young girls brought to town for the purpose, paid a "tax" that went straight into the pockets of the police, city officials and city coffers. Gambling establishments boomed, drugs and alcohol flowed. "At certain times of the year,” wrote Burton Hendrick in McClure's magazine in 1911, “the city is overrun with sailors, miners, and loggers all plentifully supplied with money and eagerly on the scent of the crudest forms of dissipation."

The number of newcomers was overwhelming in Allen's era. In 1890, Seattle’s population was a shade under 43,000. By 1910, it had ballooned to more than 237,000. Law enforcement struggled to keep up.

"The remarkable rapidity in the growth of our city, which has brought with it a constant influx of strangers and new conditions, has also made the work of the department more exacting," observed Police Chief Thomas Delaney in his 1904 official report to the city. Delaney went on to say that the “constant influx of strangers ... necessitates an unusual amount of police surveillance in surprising crime and lawlessness.”

Like today, many of the young people left home because of abuse, or because their families fractured due to hardship, disease, dysfunction and displacement. Peter Boag says that it was very difficult for single mothers, for example, to find work and raise kids. Young boys found odd jobs on the street, often selling themselves for sex in the vice districts when they weren't selling newspapers on street corners. (This, despite the state’s 1893 sodomy law.) By 1909, according to Gary Atkinson, author of Gay Seattle: Stories of Exile and Belonging, state and city morality law crackdowns virtually outlawed any sex other than intercourse between man and wife. Still, sin raged on.

Seattle bordellos were full to the brim, the "restricted" vice districts bulging with working class transients and young people. Boag says that his search of early 20th century juvenile arrest records in Portland found panhandling at saloons and young men and woman soliciting sex, including gay sex. Street kids were trying to survive, making money however they could.

Today, these things happen along motel strips like Highway 99; in Harry Allen’s time the centers of action were tiny rooms — so-called “cribs” — in Seattle vice districts with names like Blackchapel, Whitechapel or the Tenderloin. "We think of it as a contemporary problem,” says Boag, “but going through police reports I determined there really is nothing new.”

This was part of Allen's world. Piecing together the accounts of his life, it's clear that he struggled to survive. He wandered, went from job to job, and often fooled his employers. He also was fired when his gender was revealed.

In his later years, he suffered from alcohol and drugs. In 1919, his inebriated 79-year-old father stabbed a drunken Harry (almost fatally) in the back during an argument. In 1920, Allen was busted for opium. It wouldn't be surprising if his father's attack left Harry in physical and emotional pain, or if his life, lived so long on the edge, was starting to unravel.

Back then, social services were not generally available for people like Harry. There were some efforts. As the city urbanized, the police department hired female jail matrons and later added so-called “humane officers” to deal with cruelty to animals. The first humane officers, appointed by the city, wore hats and badges and patrolled the city with guns strapped to their saddles to put down mistreated livestock. Over time, humane officers became more people- focused, helping the weak, helpless, abused, neglected and lost, especially women and children. Sometimes, they would take runaways or orphans into their own homes; the jail was no place for innocent victims

Now, there are many services available for street kids — counseling, shelters, teen feeds, outreach from social workers. In Allen’s era, much of that was nonexistent. Within the police department, the female matrons and humane officers formed a thin blue social safety net, the beginnings of an organized attempt to deal with a new urban diaspora that was overwhelming young Seattle. All these years later, it’s still a challenge to meet all the needs.

One of the closest views we have of Harry Allen comes from what a providential encounter he had with a social reformer. Miriam Van Waters studied Harry’s case in the Portland prison, where Harry was serving time after his arrest for violating the Mann Act in 1912 and Van Waters, an anthropologist and women's rights advocate, was studying female prisoners for a doctoral thesis titled "The Adolescent Girl Among Primitive People." 

Historian Boag recounts how Van Waters interviewed Harry and other inmates identified by authorities as female for her kind of Orange Is the New Black study. She noted that Harry was a victim, persecuted for his independent spirit, which challenged conventional behavior. Harry’s "criminal record,” Van Waters concluded, according to Boag, “appears to be the result of discrimination."

As to Harry’s gender, Van Waters decided that he dressed as a man to get better jobs, and that he was not a "homo-sexual," an observation at odds with that of Lola Boggs, a pioneering superintendent of women for the Portland police. According to Boag, Boggs reported that Harry exhibited "an almost insane mania for making love to girls, when dressed in men’s clothing" and that Harry and his partner lived "as man and wife." Of course, Harry may have engaged in heterosexual sex work along the way too. He died in 1922 at age 40 of syphilitic meningitis.

Even today, Harry cuts a very contemporary figure: a street kid on the margins with a tough personal history. A lively charmer who acts out and lives on the edge. The kind of character who will be familiar to anyone who has seen the classic documentary Streetwise, about Seattle’s homeless youth scene, circa 1980. Harry appears in newspaper accounts of the time to have been consistent in identifying as a man. It wasn’t about fun or fashion. In that too he mirrors many modern street youth: of the 4,000 to 5,000 homeless youth in King County, an estimated 20% to 40% are LBGTQ.

Like Harry’s era, 21st century Seattle finds itself once again emerging from an economic bust into boom times. The population of those in need exploded as people struggled to find a place in an economy that had left so many homeless and on the move. Today, Seattle is one of the fastest-growing major cities in America, but it is wrestling again with issues of growth, displacement, homelessness, equity and a frayed safety net.

As a transgender person, Harry didn't get the help he needed. Society of the time was almost incapable of seeing him as anything other than a caddish pervert at worst or, at best, a charming "police character" and gender-confused Don Juan.

Harry seemed to relish the attention. He was out and proud, living his life boldly. It’s hard not to admire him as a person being true to an unconventional, unrecognized self. Society made life rough for Harry, but he pushed back, full of fight. At the same time, his traumas and trials took their toll. 

About the Authors & Contributors

Knute Berger

Knute Berger

Knute “Mossback” Berger is Crosscut's Editor-at-Large.