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Vancouver sex worker Jamie Lee Hamilton camps in front of city hall during a rally to pressure the city to fund a drop-in centre for prostitutes, on Jan. 29, 1998.

Christopher Grabowski/The Globe and Mail

One rainy winter day in 1998, Jamie Lee Hamilton climbed the marble steps outside Vancouver’s City Hall. Ms. Hamilton was enraged by the refusal of police and politicians to take seriously the disappearance of women from the city’s Downtown Eastside. In the doorway, she dumped 67 pairs of stilettos – one for every missing woman.

When then-mayor Philip Owen tried to avoid her, dashing down an empty hall, Ms. Hamilton chased after him, leading a mob of reporters. “What do you intend to do about the deaths of these women?” she yelled, pointing a red sequined shoe at the mayor. “Running away won’t solve the problem!”

It was a classic stunt by the brassy activist and proud sex worker, whom even Mr. Owen would later come to admire.

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Ms. Hamilton, who was transgender, was born James Arthur Hamilton on Sept. 20, 1955, in Vancouver, the second of two children born to Cree community organizer Alice MacMillan, a co-founder of the city’s Aboriginal Friendship Centre, and Ralph Hamilton, a foundry worker of Irish-Protestant stock.

Alice and Ralph were dirt-poor crusaders for social justice whose Downtown Eastside Vancouver home was a haven for dissidents and a frequent meeting place for the Communist Party. The family’s meagre fortunes were further reduced when Ralph was waylaid by silicosis, a lung ailment caused by the inhalation of silica, and had to stop working.

It was a vulnerable time for Jimmy, as Ms. Hamilton was then known. The tall, delicate 12-year-old walked with a sashay, was nicknamed “Indian princess” and suffered from relentless bullying.

At 15, Jimmy found the Taurus Spa, a downtown steam bath.

“We felt safe at the Taurus,” explains David Bates, who met Jimmy there. “We could escape the dark world outside.”

They were part of a brash group of misfits and runaways who worked at the Taurus by day and hustled by night.

It was risky work. Jimmy was once molested by a cop and threatened at knife point by a customer.

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Jimmy’s closest friend at the time was Sandy St. Peters, Vancouver’s reigning drag queen throughout the 1970s. By 17, Jimmy was appearing alongside her as Flo. At BJs, the city’s earliest drag bar, Flo sang It’s My Time, a tentative first step toward living her true self.

After decamping for the Okanagan town of Osoyoos, Jimmy, who had begun taking hormones, adopted the name Jamie Lee. She found a job as a waitress, fastidiously waxing her face to help keep her past as Jimmy a secret. It was a dangerous time to be trans. After a year, she felt comfortable enough in her skin to return to Vancouver and live openly as Jamie Lee.

Her father had by then died. Accepting her child’s transition didn’t come naturally to her mother, Alice, whom Ms. Hamilton adored. She sought guidance from Rev. Barry Morris, her minister at First United Church, a Downtown Eastside institution.

“You’ll always have me as a son,” Mr. Morris remembers Ms. Hamilton telling her mom. “But I need you to understand who I am.”

In Vancouver, Ms. Hamilton returned to hustling. She was a streetwise, mother-hen figure in the gay village in Vancouver’s West End. She encouraged trans sex workers to work in pairs, and jot down customers’ licence plates, and she raised the alarm about bad clients.

But in 1984, a powerful anti-prostitution lobby, the Concerned Residents of the West End (CROWE) managed to have prostitutes, whom they deemed a threat to “public morality,” expelled from the neighbourhood. This would ultimately push the city’s low-track sex workers to the poorly lit, industrial outer reaches of the city’s Downtown Eastside. Almost immediately, they began disappearing.

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A string of grisly murders of trans and Indigenous women in the early nineties jolted Ms. Hamilton to action. She began patrolling the Downtown Eastside late at night with Mr. Morris, doling out hot coffees. She opened Rainbow’s End, a Downtown Eastside thrift store where trans women could get a makeover and support, and founded Grandma’s House, where sex workers could get a hot meal and check in to a registry, letting their families know they were safe. In 1996, she became the first trans woman in Canada to run for political office, seeking a seat on city council. She lost.

Friends say she was powered by the painful adversity she faced – as an Indigenous child, queer teen, trans woman and sex worker.

In 2000, Ms. Hamilton rented a space on Pandora Street with the goal of challenging the constitutionality of the country’s bawdy house law and keeping Downtown Eastside sex workers safe. She opened a brothel named Pandora’s Box, taunting Vancouver police, daring them to arrest her – which they promptly did. The charges against her, however, were ultimately stayed. Robert (Willy) Pickton had just been arrested, and the serial killer had been using the Downtown Eastside as his hunting grounds.

In 2016, Ms. Hamilton co-founded Canada’s first memorial for sex workers, a retro lamp post with a red bulb in Vancouver’s West End. Mr. Owen, the former mayor, joined her for its unveiling.

It took Ms. Hamilton 35 years, but last August, she finally returned to live in her beloved West End – “still an unrepentant and unapologetic ho,” she told friends.

Her bravura masked a deep pain. Ms. Hamilton had been diagnosed with cancer, but was keeping it secret. Her friends knew something was wrong. She seemed suddenly frail, more vulnerable, quick to cry.

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Late last month, she moved to Cottage Hospice, and sought out Mr. Morris, who remained a confidante. She wanted to be baptized like her mother. She was afraid to die, she told him. Mr. Morris tried to reassure her she would be “accompanied to the end.”

On Dec. 21, Ms. Hamilton’s friends, including some of her old political foes on the right, gathered at her bedside. After she received the sacrament of belonging, they sang Amazing Grace a cappella. Ms. Hamilton died 30 hours later, on Dec. 23. “The city has lost its most fierce advocate,” said Judy Graves, a former advocate for the city’s homeless. She was 64.

A celebration of Ms. Hamilton’s life will take place on Jan. 25 at 2 p.m. at St. Paul’s Anglican Church in Vancouver’s West End. Dress code: “Fabulous.”

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