Homeless, now housed: How friendship helped Leslie Pilgrim off Windsor's streets

Leslie Pilgrim wants to get a dog, but right now he's fine looking after his neighbour's feline, 'Kitty Kat,' as he calls her. 

For Pilgrim, looking after someone's pet was a simple long shot when he considers where he was in 2015 — addicted to drugs, living on Windsor's streets and searching for a way to save a buck.

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"I'm doing pretty good, feeling good about myself," said Pilgrim, sitting on a bench outside of Family Services Windsor-Essex. 

It's the staff at that centre that have helped Pilgrim become one of 230 people that have been housed through the Windsor-Essex Housing Connections program since it started in July of 2016.

During a month when volunteers are counting the homeless across Windsor, here's a story of how someone ends up finding housing. 

Homeless, helpless — hopeful

"I just couldn't get it together," said Pilgrim, thinking about his struggles of living on the streets in Windsor without a safe place to sleep at night. 

Pilgrim said he was "worn thin" as he battled addiction issues while sleeping in fields, under bridges and on church steps.

"What was I battling? Anything that could take away the reality of what I was going through," said Pilgrim. 

"Alcohol, marijuana, crystal meth — it didn't matter, whatever I could get my hands on."

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​Today Pilgrim said he's clean, hasn't smoked a cigarette in nearly a month and has been living inside of the upper story of a house for more than two years. 

He said a big part of his fortune is because of friendship.

Outreach and follow-up

Pilgrim said life was lonely in August 2015, battling "mental stresses" on the third floor of the Hotel-Dieu Grace in Windsor. 

That's when Colm Holmes and Matt Goudreau with Family Services Windsor-Essex Housing Connections program walked into his room. 

"Who's this big tall guy and this really short guy?" remembers Pilgrim, describing Holmes and Goudreau walking into his room.

Both men explained the services they could help connect Pilgrim with to find housing.

"I thought wow, this is a godsend."

Housing first — but not only

"Workers like myself and my two colleagues will do street outreach and it will be targeted and it will be coordinated," said Holmes, the shorter of the pair. 

Holmes is often the first point of contact for people living on the streets and looking for housing, one of three outreach workers with Family Services Windsor Essex.

He said that getting someone into secure in safe housing is the first step on a process that can't end with handing someone a set of keys. 

"That ongoing support really helps people retain the housing that they've secured. It's important for us to help individuals to navigate that," said Holmes.

Once Holmes makes contact and builds a relationship with someone who wants to start looking for housing they're handed off to people like Goudreau, the other man who entered Pilgrim's hospital room that August day. 

I mean I grew an attachment to Matt and Colm right away, they're wonderful people and very good friends,- Leslie Pilgrim

"The idea is that someone who is experiencing homelessness is housed first and then they start to work on some of their long-term goals," said Goudreau, who remembers when that approach was reversed. 

He said by approaching homelessness with a housing-first model, it helps people getting housed find help for things like mental health and addictions issues.

Pilgrim was able to secure a one bedroom rental in March of 2016 with the program's help and has had secure housing since.

Now he's now giving back to the community with donations, volunteer work and for some, a warm place to stay. 

"I've opened my door to let people who are homeless as well that are waiting for the program or that are on the program waiting to be house, I invite them into my home and let them live with me," he said.

"It's a beautiful thing to be able to reach out and help other people."

A house and a friendship

Pilgrim said the program covers two thirds of his rent each month but his eyes light up when he talks about what else the program has secured for him.

"I mean I grew an attachment to Matt and Colm right away, they're wonderful people and very good friends," said Pilgrim. 

That friendship continues through the random encounters Holmes and Pilgrim share while they're out around Windsor during the day. 

Goudreau sees Pilgrim once a week during visits where they sort out any troubles Pilgrim may be facing and continue looking for services to keep him on the right track. 

"It's also just things like getting a phone, getting a gym membership, connecting with family," said Goudreau. 

"It's wants and needs and it's very much their life, they're in the driver's seat and so they direct the service."

For Pilgrim, he's excited to jump into Goudreau's vehicle for a ride home — his own home — and take care of his neighbour's cat.

"It's good to be able to know that I have a nice warm bed to go in to and I'm not going to be looking under a bridge to sleep under tonight," said Pilgrim.