In the winter of 1911, a handsome young man arrived in Meeker, Colorado. He wore a smart suit and introduced himself to the residents as John Hill — or Jack, as he preferred to be called. No one in that small White River Valley town had ever seen him before. He was in his early 20s, and had come from the east, he said, to be revived by the bracing western winds.
His first job in the town, however, was not out on the plains, but at the local saloon owned by one John Davitt. Handsome and well-mannered, Jack was instantly popular with the Davitt House's patrons, working his way up from dishwasher to barroom porter, before finally achieving the status of bartender. Though he did not join the town's men in their drinking — a quirk which soon earned him the title of "Davitt's teetotaller" — the men did not begrudge him his temperance. Jack was adept at minding his own business, turning his attention to a dirty glass or unswept floor when their profanities drifted across the bar towards him. If he heard them at all, or disapproved of their risqué talk, he did not show it, and for this he earned their unspoken respect.
Jack's stoical charm was not only popular with the men of the town. Enamored of his thick curls and smooth face, tanned from his work on the ranches, the local girls looked with interest upon their newcomer. Within a week of his arrival, they had rechristened him "Handsome Jack," and within three they had collectively voted him "the most handsome and captivating" man in town, according to the Herald Democrat.
Popular, hardworking, attractive — Jack Hill was, to all appearances, a very successful Meeker man.
The people of Meeker weren't to know — at least not yet — that this quiet youth who mixed their drinks with sober care and politely returned their blushing glances in the town's streets had, only six years previously, been living under a very different name in nearby Coal Creek, Colorado. Indeed, as recently as 1907, "Jack Hill" had been known not as a barman but as a teacher — a young woman by the name of Helen A. Hilsher.
Where Helen Hilsher was born or what her life was like before she arrived in Meeker it is, for the most part, difficult to say. Births were not required to be recorded by the state of Colorado until after the turn of the century, but if the age she gave when living as Jack Hill is to be believed, Hilsher was born in 1891. She lived for a while working as a teacher in Coal Creek, a town about 200 miles from Meeker and where, according to her landlady Mrs. J.J. Ross, she had been "unusually popular." Despite this popularity, however, Coal Creek was too small an arena to play adequate host to Helen Hilsher's ambitions. Sixteen years old, evidently intelligent and charismatic, but with little or no family or money behind her, Helen was already itching for a way out, searching the stores of her considerable ingenuity for an answer to the problem of her situation.
In 1909, Helen found the answer she was looking for. She donned a suit and cut her hair, and made the journey 90 miles east — to the nearby town of Wiggins, Colorado.
It was in Wiggins that "Jack Hill," according to the newspaper records, first came to life. He arrived without great incident, and immediately took up residence on a 160-acre homestead 12 miles southwest of the town. He was as popular in Wiggins as he would later be in Meeker. Known affectionately among his fellow ranchers as "little Jack" due to his slight physique, he also prolifically courted the town's women. He even developed a close relationship with one young woman, though her name unfortunately escapes the written record. They were frequently seen out riding together in the Sunday dusk, two slight forms trotting side by side in the dying light. For two years, Jack Hill lived happily in Wiggins.
In September 1911 Hill went to Denver with a group of young male friends, brought to serve as witnesses in a legal matter. Hill was there to prove that he was the rightful owner of land bought under the name of Helen Hilsher, and he took it as an opportunity to reveal his past identity to his new friends.
Changing into feminine clothing on arrival at the Denver town hall, Hill presented himself to the group as "Helen" for the first time. Perhaps predictably, the men were disbelieving. According to one report, Helen was forced to remove the wig she had donned for the occasion, and to resume her masculine gait and tone of voice before her friends would finally believe that she was indeed their friend "little" Jack.
"It was the only thing to do," said Hilsher afterwards, speaking to a reporter from the Yuma Pioneer who visited her at her home in Denver. "A woman would not have felt safe out there alone, and I just had to do it. Now that it is all over I feel awful about it — but, I am glad I won."
This declaration of victorious and satisfied retreat from the masculine world may have been palatable to local newspapers and their readers, but the story wasn't picked up in Denver or nationally. It had the air of a completed sideshow, a party trick. As far as the papers were concerned, Hilsher had packed away the circus and costume and settled back into the life proper to her as a young woman in that early phase of the twentieth century. Her jaunt in Wiggins was merely a flight of feminine fancy: a local gossip piece.
This was a false impression.
Within months of Helen's departure from Wiggins, Jack Hill arrived in Meeker.
Read the rest of this story at Narratively.