From Whiteout to down and out Jets co-owner says it's 'patently unacceptable' to see downtown go from thriving to struggling as he battles to improve the city's core   By: Mike McIntyre Posted: 7:26 PM CDT Monday, Jun. 9, 2025 Last Modified: 11:12 PM CDT Monday, Jun. 9, 2025 Updates

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Vulnerable people passed out and sleeping on sidewalks, in front of businesses and on park benches. Visible signs of addiction and mental illness at seemingly every turn. Desperate panhandlers teetering on concrete dividers hoping motorists will toss them some change.

These were the scenes obvious to anyone in downtown Winnipeg on Monday afternoon — ones that Winnipeg Jets co-owner and chairman Mark Chipman experienced first-hand as he made his way into a Main Street building for an event much bigger and more important than any hockey game.

“I just don’t know how we can look away from it,” Chipman told the Free Press during a candid, wide-ranging one-on-one chat. “It never ends. Just driving over today … you can’t drive a block without being reminded of somebody that is really suffering.”

Chipman noted the stark contrast of how the inner-city was bursting with energy and excitement during the seven Jets home playoff dates earlier this spring, with more than 15,000 fans cheering inside Canada Life Centre and thousands more at the outdoor street parties.

But what happens once the buzzer sounds, the game ends and the crowds head home?

“I just find it patently unacceptable,” Chipman said of the challenges facing so many citizens.

The painstaking, often frustrating work to address what he calls a “complex, multi-generational set of issues” continues, with days like Monday providing hope that progress is slowly being made.

Chipman stood front and centre inside Okichidah Pimahtisiwin Kiskinawmatowin (OPK), with Jets defenceman Dylan DeMelo at his side, presenting a cheque for $234,890 to the United Way which represents 50 per cent of the proceeds from the playoff events held earlier this spring.

“It never ends. Just driving over today … you can’t drive a block without being reminded of somebody that is really suffering.”–Mark Chipman

The funds will be shared equally among four grassroots organizations working to combat issues of addiction, homelessness and mental illness.

“It’s just incredible,” said Connie Walker, the interim president and CEO of United Way who recently returned to the organization she had previously been with between 2008-2023. “I didn’t realize just how big the cheque was.”

It’s the biggest single playoff contribution since True North and United Way began partnering together in 2019 — and it comes just in the nick of time.

“I’ve been taken aback by the level of need in our community,” said Walker. “Every day, any time of day, I can look out my window and see people struggling. More people than I have ever seen before. It’s not right. I find it heartbreaking.”

Chipman said it was a similar glance outside from his office back in 2014 that led to a personal awakening.

A dishevelled, disoriented man was clearly in some distress. He watched as first responders, paramedics and police showed up to deal with him. Chipman had viewed similar scenes countless times over the years. But this one, he says, stuck with him. He had seen enough.

“I got really curious about what was happening to this soul. Where is this soul going?” Chipman said. “That just took me down a path that I’m still very much on and have spent a lot of time trying to understand and offer solutions to.”

OPK, which works with marginalized, at-risk Indigenous young adults, are one of the four recipients of this year’s funds.

“It’s been a tsunami of need,” said OPK Executive Director Sheryl Blacksmith. “Helping our young people to realize their dreams, to realize their potential, to forgive themselves. Failure is a great teacher. Thank you so much for this amazing gift and how much it’s going to change lives.”

Blacksmith drew plenty of laughs when, looking directly at DeMelo, she admitted to being “a little star-struck…Dylan, I’m your No. 1 fan. I was more nervous about being in your presence than anything else. Just know that you are our heroes.”

DeMelo, an Ontario product who now lives year-round in Winnipeg with his family, embraced her with a hug.

The other recipients this year are N’Dinawemak – Our Relatives’ Place (an Indigenous-led resource offering 24-7 space for individuals experiencing homelessness), the Downtown Community Safety Partnership (which provides 24-7 non-emergency support, outreach and intervention) and Kã Ni Kãnichihk – Velma’s House (a shelter for adult women).

“The gravity of the situation is very serious. Having said that, I think in many ways I’ve never been more hopeful,” said Chipman, noting ongoing initiatives at both the provincial and municipal level which he and many other partners are involved with.

“Because I’m sensing a real willingness of all those interested parties to work together. We’re at an intersection here, and we’re going to go one way or the other here. I think we’re really close now. Parts of it are finally coming together.”

Whether it’s on or off the ice, there’s no question the Jets have always had a strong connection with the community, re-enforced by losing the NHL back in 1996 only to get a second chance in 2011. Chipman, who along with business partner David Thomson purchased the Atlanta Thrashers 14 years ago, believes this year’s hockey club only solidified that bond.

True North made a concerted effort to re-connect with old and new fans, due in part to a decrease in its season ticket base and overall attendance. They made significant progress on that front while overseeing a team that won the Presidents’ Trophy, beat the St. Louis Blues in an epic seven-game series and then eventually fell to the Dallas Stars in six games.

“We were really a good team from start-to-finish. Getting past the first round, and the way it was done so dramatically, helped,” said Chipman.

“Every day, any time of day, I can look out my window and see people struggling. More people than I have ever seen before. It’s not right. I find it heartbreaking.”–Connie Walker

“But when I think about our team, I think about the core of our team. It’s that group of men that really represent us I think people connect with. They’ve watched them grow up. That maturation process revealed itself in some very difficult circumstances.”

None greater than first-ever draft pick Mark Scheifele learning his father, Brad, had passed away just hours before a pivotal Game 6 in Dallas. Scheifele ultimately played in the game, scored the opening goal, then took a late penalty that led to the overtime winner by the Stars.

Jets players and fans immediately rallied around him, and Chipman chartered a plane to take the group to the funeral several days later.

“The way our group rallied around Scheif left an impression on me. I can’t tell you I’m surprised, because I’ve watched these guys grow into men together. But it still left an impression that I’ll never forget,” said Chipman.

“It was just so authentic and genuine and real that I think people connected with it. Schief was everybody’s son.”

On the hockey side, Chipman said the ultimate goal remains delivering a Stanley Cup to Winnipeg. He believes this group is closer than ever to making that happen.

“It’s been a work-in-progress. This group didn’t all of a sudden just emerge into what they showed themselves to be. They’ve been becoming this group for many, many years now,” said Chipman.

“And what excites me is they’re going to continue to be this group for the foreseeable future. I think that’s what’s really resonating with people.”

And, as Monday showed, that can be a real win-win for everyone.

“It’s one of the great privileges of being involved in this business of professional hockey,” said Chipman.

“That you can associate with organizations like this and try, in some incremental way every year, to make the community a little bit more healthy and stronger. Hopefully we can do this again next year and maybe the cheque is a little bit bigger because we go a little bit deeper.”

mike.mcintyre@freepress.mb.ca

X and Bluesky: @mikemcintyrewpg