Paula Tookey always knew she would end up at Kevin Dickman’s funeral.

She also knew his death would be as heartbreaking as his life.

Dickman’s body was pulled from the Don River on Oct. 5, a month after he lost his housing — again. He was 62.

He struggled with mental illness and homelessness for most of his adult life.

“You hated being homeless — being dirty, tired and cold. Being alone,” Tookey said, addressing Dickman’s pine casket in the chapel of the Rosar-Morrison Funeral Home on Sherbourne St. on a grey afternoon last month.

“You often broke into schools and garages to sleep. You were in and out of emergency rooms, and in and out of jails for years. Decades,” said Tookey, who befriended Dickman in the early 1990s when she was working at the now-closed StreetCity transitional housing project.

“I loved you Kevin. We loved you,” she continued as several dozen homeless support workers sat solemnly in the wooden pews, some weeping openly. “But I couldn’t promise that it would get better. For people like you, it rarely does.”

Dickman is among scores of homeless people who have died in Toronto this year, including more than 30 who used the city’s shelter system, which has been running at or near-capacity since the summer.

On Thursday evening, the Ontario Coalition Against Poverty (OCAP) held a vigil outside the city’s Peter St. emergency shelter referral centre where Dickman lined up nightly — often in vain — for access to a bed. Capacity has doubled in four years to over 7,000 permanent beds and about 600 temporary and respite spots. And still people are turned away.

The coalition is demanding the city open 2,000 new shelter beds to prevent more deaths this winter amid Toronto’s worsening affordable housing and homelessness crisis.

The city, which released its winter shelter plan earlier this week, plans to add almost 500 new permanent and temporary beds. But activists say this comes nowhere close to meeting the need.

Despite Dickman’s age, troubles with mental illness and substance abuse, those who knew him say he seemed like a little boy.

“I always called him ‘smile boy’ and we would laugh and laugh,” said Chaudhry Ahmed, harm reduction project co-ordinator at StreetHealth, a downtown agency that supports the homeless.

“He was always asking about our kids,” added Myra Hewson, another StreetHealth worker. “He loved babies.”

But Dickman was also the boy who got “stuck in time and hurt,” whose childhood was stolen by sexual abuse, said Tookey, who runs the safe injection site at South Riverdale Community Health Centre and was Dickman’s caseworker at StreetHealth a decade ago.

Tookey, 53, knew him the longest — almost 30 years — and said she “often thought of him like a brother.”

“He struggled with loneliness in the worst kind of way … he felt the world was against him,” she said in an interview.

“There were times he would come into my office sobbing like a little boy, pouring out his broken heart. He had so many losses that he couldn’t understand.”

Dickman was born in Belleville and adopted into a Brampton family. He had happy memories of his early childhood, including a trip to England with his family that was “definitely a highlight,” Tookey recalled Dickman telling her.

But when he was about 10, his father died unexpectedly in hospital during a routine medical procedure. Dickman was devastated.

Kevin Dickman wrote a poem about his struggles with addiction. He struggled with mental illness and homelessness for most of his adult life.

In an attempt to ease his sorrow, his mother contacted a local mentorship agency who paired Dickman with a police officer. But the man was a pedophile, a horror revealed by one of the other boys the officer was also molesting. As far as Tookey knows, the abuser was never prosecuted.

As Dickman grew up, that trauma translated into angry outbursts, petty crime and substance abuse that eventually caused his family to sever ties.

Years later, Dickman was heartbroken when he learned his mother had died and nobody told him, Tookey said.

No one from his family attended his funeral.

A capacity assessment by the Centre for Addiction and Mental Health that formed part of his trial for auto theft and drunk driving in 2003, also referred to the childhood sexual abuse and his subsequent mental health challenges.

“Kevin was diagnosed with mental illness — schizophrenia — but the trauma he endured was never acknowledged,” Tookey said.

His anti-psychotic medication didn’t appear to manage his symptoms — the voices in his head, the explosions of anger and erratic behaviour — and like so many homeless people, Dickman turned to alcohol and prescription and street drugs to ease the pain.

His trajectory appeared to change when the judge at his 2003 trial — who took Dickman’s medical history to heart — sentenced him to a mental health treatment centre in Brockville, where Tookey says he was surrounded with kindness and humanity.

For perhaps the first time in his life, he got treatment. He participated in programming. And he started to get better, Tookey said.

When he was released a year later, just before his 50th birthday, Tookey helped Dickman get an apartment with support. And he thrived.

“Kevin got a job as a peer worker, he got a cat, he felt hopeful,” she said. “He began to feel his life had a purpose. He loved to feel useful.”

But after several years, his support worker got another job. Dickman never connected with her replacement and eventually, he ended up on the streets again.

His last home was The Edwin, a transitional housing program for older men on Queen St. E. But that fell apart over the summer.

Toronto Employment and Social Services funded about 2,100 funeral, burial and cremation services last year for people who lived on welfare and others who died with no money to cover the cost. Of those, just over 200 were “Coroner’s Warrants,” which often include the homeless, like Dickman.

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A traditional funeral service costs almost $5,000 and is paid for by the province through the Ontario Works Act. In 2018, the province reimbursed the city $8.4 million for funeral and burial costs.

In cases where the deceased does not have a plot, burials are usually in cemeteries outside the city where space is more readily available and less costly.

A number on a small metal plaque in the ground is usually the only marker. Names are kept in the cemetery’s record system.

Services for the homeless are particularly heart-rending, said Father Larry Whissell, a Catholic priest who presides over many of them with a mix of outrage and levity.

After Tookey’s eulogy, Whissell began his homily for Dickman by leaning over the pulpit and shaking his head.

“Don’t you know the 11th commandment is don’t upstage the priest?” he teased.

But his words quickly turned to the tragedy of Dickman’s death.

“We, in Canada, live in one of the richest countries on earth. There is no excuse for anyone not having a roof over their head. There is no excuse for anyone going hungry who needs to eat,” he said.

“And yet here we sit, mourning the death of someone who died homeless. And undoubtedly hungry,”

Whissell talked about Dickman’s contributions, his work with StreetHealth as a peer researcher, his training as a harm reduction worker for crack users and media interviews he gave to help others understand the challenges of homelessness.

“He’s flying with the angels. And if he’s doing it properly, he’s probably making some trouble with the angels,” Whissell said to a few knowing smiles.

After the funeral service, five outreach workers accompanied Dickman’s casket on the hour-long drive up the Don Valley Parkway and across Highway 401 to Duffin Meadows Cemetery in Pickering.

At the gravesite, a windswept hilltop lined by a new housing subdivision, Whissell tucked a cigarette into the arrangement of yellow roses and daisies that adorned his casket.

“I think he would have liked that,” he quipped.

“The social safety net is supposed to catch people like Kevin,” Tookey said this week as she sifted through letters, notes and drawings Dickman gave her over the years.

“But only if you behave nicely. Otherwise, people don’t want to deal with you — and you default to the criminal justice system.”

For Tookey, and many of the outreach workers at his funeral, Dickman was a teacher.

“He taught us through his suffering — and being insufferable,” she said sadly, recalling his “very challenging” behaviour when he was mentally unwell.

“He helped us to become better people. He continuously gave us opportunities to practise patience.

“I am who I am today, thanks to Kevin. He was a huge part of my life, whether I wanted it or not. And I am very grateful for what he offered.”

At StreetHealth, outreach worker Jessica Slotnick recalled Dickman’s distress in the last weeks of his life, after leaving The Edwin, his home for about four years.

When he left, he took his cat, Nutella, and bought a GO Train ticket to Brampton to visit a friend, she said. But when he let Nutella out of the carrier to stretch after the journey, the cat ran away. Dickman was gutted.

As always, Dickman returned to StreetHealth for support. He didn’t have a phone, so he would go to the red-brick house at Dundas St. E. and Sherbourne St. to call the city’s shelter referral service to reserve a bed for the night.

“Often we were put on hold or told to call back in two hours,” she said.

But by then StreetHealth would be closed and Dickman would be forced to walk almost three kilometres to the Peter St. referral centre and wait there. Sometimes he would wait until midnight to get a bed. Sometimes he’d sleep rough, she added.

It’s not clear how Dickman ended up in the Don River. Tookey thinks he became so disheartened that he just gave up.

“I remember how much he suffered physically, emotionally and spiritually from being homeless when he was in his 30s and 40s,” she told the OCAP vigil on Thursday night.

“I can’t imagine how Kevin felt when he found himself back there again, without a place to go, having nothing and no one,” she said.

“I know for a fact that if Kevin had a place to go, a place to be, he would not be dead.”

Kevin Dickman was part of a short documentary film shot in late 2004 about finding homes for the homeless. The film aired on CBC’s Moving On in January, 2005.

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