A Winnipeg artist who once lived on the street has landed a gig most hockey fans would be envious of.

But for Jamie Hogaboam, painting the portraits of inductees to the Winnipeg Jets Hall of Fame isn't just a cool job — it's a chance to bring attention to the issues of mental health and homelessness.

In 2015, Hogaboam was driving a cab, working 70 hours a week, and barely making enough to pay bills. In addition, he was battling mental illness.

"I was diagnosed with borderline personality disorder. And I just got diagnosed in the last couple of years," he said.

A Winnipeg man, who once lived on the streets, is doing a job that so many of us would be envious of. Jamie Hogaboam painted for most of his life. And a letter he wrote to the owner of the Winnipeg Jets changed his life. 2:13

Hogaboam says he thought about suicide, he tried to seek social assistance, but was denied. He eventually started living with a friend and learned about the Art Beat studio in Winnipeg.

"The people at Art Beat deal with people with mental illnesses all the time. 'Cause 60 per cent of our artists, alumni artists have been homeless at one time."

Jamie started painting again, something he's done since childhood. One of the first things he remembers painting as a child was a cardboard cut-out of L.A. Kings goaltender Rogie Vachon, to use as a practice target.

A painting of Winnipeg-born Detroit Red Wings player Terry Sawchuk proved to be pivotal in Hogaboam's life. When he started working on it, Hogaboam learned that Sawchuk had also lived with untreated mental illness.

"He had conflicts, confrontations with fans and coaches and this and that. I said, well that's all because of the mental illness. But he became the best goaltender to ever play the game. So it inspired me," Hogaboam said.

He put that painting on a card and sent it with a letter to Winnipeg Jets co-owner Mark Chipman. He told Chipman how art helped him with his mental illness, and asked Chipman to come visit the studio in the Exchange District.

Chipman accepted the invitation, and Hogaboam says the had a long conversation about hockey and mental health.

At the end of their meeting, Hogaboam got an offer he just couldn't turn down.

"He turned to me and said, 'OK, Just tell me what it's going to cost and tell me when do we start?' And I said, 'OK, do it, we're here,'" Hogaboam said.

Hogaboam painted this portrait of Dale Hawerchuk for his induction into the Winnipeg Jets Hall of Fame. (Tyson Koschik/CBC)

The Jets commissioned the artist to paint all the portraits for the hockey club's hall of fame. His first task was to paint the portrait of the team's first inductee, Dale Hawerchuk, and got to meet him at the hall of fame luncheon.

"I'm standing here with the greatest Winnipeg Jet of all time, one of the greatest hockey players that played the game, and he's telling me how great I am."

Hogaboam is now tasked with painting the famous "Hot Line" of Bobby Hull, Anders Hedberg and Ulf Nilsson.

"When we made the decision to induct Dale into the Hall of Fame, Mark thought, this is just the natural opportunity to commission Jamie to do this painting. He's a very passionate hockey fan, he's a passionate Winnipeg Jets fan," said Rob Wozny, vice-president of communications and community outreach for the Jets.

The Winnipeg Jets played against the Nashville Predators Monday night.