‘She’s kind of that unicorn’ The premier’s chosen leader in the fight to end chronic homelessness walked away from the job less than a year in; Tessa Blaikie Whitecloud believes she’ll have greater impact by attacking the crisis on another front By: Scott Billeck Posted: 2:57 PM CST Friday, Nov. 21, 2025

If there is one thing Tessa Blaikie Whitecloud knows, it’s that tackling Winnipeg’s homelessness crisis requires support and ideas from all corners of the city.

She has witnessed the crisis’s impact first-hand while CEO of Siloam Mission. More recently, she worked to bring together government, social agencies and other key players together to get Manitoba’s Your Way Home strategy firmly established.

And on Dec. 1, she will become the president and CEO of the Collaborative Housing Alliance — a new organization, with an attached real estate investment trust and charitable foundation to come, created to partner with the private sector to address the severe shortage of safe, low-cost places for people to live.

They’re all different perspectives addressing a common goal — providing stable housing for thousands who need affordable and “deeply” affordable housing in the province.

“(It’s) a natural progression, it makes complete sense,” Blaikie Whitecloud said, talking about a career that began in mental health before pivoting to housing and homelessness following the suicide death of a friend who lost his home.

Although her decision to step down as Premier Wab Kinew’s hand-picked senior adviser on homelessness after only 10 months came as a surprise, she said the move was simply the next step in a career helping people living on society’s margins.

“My whole career has been guided by, ‘Where’s my opportunity to make the most impact?’ The role of senior adviser was new. Is it long-term? Is it short-term? We didn’t know.”

The split was amicable, she said. “We’re all tight.” Her focus is on increasing the supply of housing units, a process she and trust chair and former Canada Life CEO Paul Mahon acknowledge will take several years but in the end provide what’s long been needed and ignored.

“I have a lot of confidence in the province’s plan,” she said, adding that her work at the alliance — building a provincewide housing system — will include providing funds for non-profit housing projects and increasing the availability of affordable units, giving people an alternative to a life on the streets.

Part of Blaikie Whitecloud’s role with the province was to build infrastructure to get government and sector partners to the same table. That table already existed in the social-services part of the equation; her work ensured the province was seated there, as well.

“It was about putting in place structure, process and collaboration. That’s important work. But that’s not leveraging everything Tessa has to give,” Mahon said, adding her fundraising ability, connections and ability to work with government will have “higher impact.”

“Our view is, we will be there to support Your Way Home, but we also want to build a broader portfolio of solutions that includes regular affordable housing, which goes well beyond what Your Way Home is about.”

He stressed it isn’t the alliance versus the government, but rather helping to expand the availability of housing that will benefit the strategy, situated between the provincial work of clearing encampments and private-sector market-rent housing.

“We’re allowing people to move up the continuum,” Mahon said, noting that Your Way Home helps people into supportive housing, whereas CHA will be focused on building the next step on the housing ladder.

Blaikie Whitecloud said the move from the province will let her work differently, knowing systems now exist to house people with needed supports as units become available.

“We have clear provincial investments and a commitment to 2031, which will mean more deeply supportive and deeply affordable housing,” she said, adding there is and will continue to be a need for affordable units as formerly homeless people “graduate” to the next level.

In Canada, housing is considered “affordable” if it costs between 10 per cent and 30 per cent below the median market rate in that area according to data gathered by the Canada Mortgage and Housing Corp.

“Deeply affordable” housing costs 30 per cent of a household’s pre-tax income; for example, someone without an income would pay nothing, while someone earning $1,000 every month would pay $300 in rent.

More than 100 people have been housed since the provincial strategy was announced last January, and some have already moved from transitional to affordable units.

Blaikie Whitecloud, responding to criticism that the strategy wasn’t moving quickly enough, said that while speed may have been wanting, retention matters.

“You can move a lot of people, but if you’re not actually intervening in a way that keeps them stable… you can further entrench people,” she said.

“You can move a lot of people, but if you’re not actually intervening in a way that keeps them stable… you can further entrench people.”

Demand far outpaces supply. About 100 affordable units are opened monthly; roughly 3,000 people need them.

And people in affordable settings are struggling. Siloam Mission feeds hundreds each day. A third of them have a roof over their head, but can’t afford rent if they want to eat.

“We’re seized with the need for deeply supportive, deeply affordable units,” Mahon said. “But if we just did that, we would have a big problem, because we then need affordable places for people to move to.”

He acknowledged private-sector involvement can cause concern.

“The mission is not for somebody to make a lot of money,” he said. “The mission is to get at the housing challenges we have. It’s intention is not to be a private-sector initiative. It intends to draw on private-sector resources, to be part of a collaborative initiative, is the way to think about it.”

Some profit is necessary to reinvest and pay staff, he said, but the first two projects — soon to be announced — will have no profit at all. Long-term sustainability will rely on “just enough profit,” in addition to ongoing fundraising from donors and securing capital from investors.

“How do we actually create something that’s lasting, that has continuity into the future?” he said. “The way you do that is, get a mix of properties, get people who are willing to give back as they provide services, such that there’s enough resources to flow back into the system to keep it going.

“Saying that, it will be just enough profit. That won’t be the thing that will sustain it into the future. What’ll sustain will be ongoing fundraising, ongoing raising of capital. And the money we raise in the foundation will be clearly charitable giving that people want to make a difference.”

Money raised through the CHA foundation will come from charitable donations. On the REIT side — a REIT is a company that owns and typically operates income-producing real estate — Mahon expects investors to receive anywhere from zero to low percentage returns, with any profit above that reinvested into other CHA projects — similar to the way a social impact bond might work where the return is a societal benefit.

“It’s a little bit like the United Way; lots of people give to the United Way, but they want to see metrics of, how did it actually help in Winnipeg?” Mahon said.

He said transparency will be essential to long-term sustainability — for private donors, investors and the public. He noted that many organizations struggle to provide clear data, but believes this one must show concrete results, such as how many units and beds have been created.

“The true lagging indicator, the one that really matters, is how have you lifted up someone from living in the streets in poverty to a life where they’re living their best possible life? Have you truly made a difference in people’s lives?” he said.

“If I’m someone who wants to really understand whether this is working, I’m going to want to say, ‘How is this actually changing the trajectory of houselessness? Care for people with addictions, acquired brain injuries? Reducing (the number forced into the streets)? All those things. So we’re going to have to get there. The financial data shouldn’t be enough.”

Mahon is backing the project not only with his words but his wallet. He and his wife Anne have contributed $2 million through their family foundation. True North Sports and Entertainment is adding $5 million. And the province has provided CHA with $10 million in seed capital to begin leveraging private, public and philanthropic funds.

The CHA REIT, developed by the Business Council of Manitoba, was first announced in October 2024.

“You cannot have a successful economy, you cannot have a successful business without a healthy community.”

“You cannot have a successful economy, you cannot have a successful business without a healthy community, and that’s really what the membership wants,” Bram Strain, the council’s president and CEO, said last month.

“The membership wants a healthy community, and this, to me, is putting your money where your mouth is. This is… action. This is doing something.”

Blaikie Whitecloud said there are many business people in Winnipeg, and some who’ve moved away, who care about the community and want to see a successful model for housing and a solution for homelessness.

When CHA was just getting off the ground, Blaikie Whitecloud had just signed on with the province.

“Tough timing,” she said.

Mahon insists he would never have approached her for the CEO role had she not already built the provincial system to the point where it could sustain itself.

One thing he is absolutely certain about is that Blaikie Whitecloud was the right person for her new job. Mahon explained that at first, he figured hiring a prominent name in real estate would suffice. As time went along, his tune changed.

“If you think about Tessa, her background in social services, her background in working with the province, her background in raising money — she’s kind of that unicorn with those capabilities and skills,” Mahon said. “So that’s where we landed. It’s been a journey of finding what’s the right recipe.”

It’s a “generational project,” as Mahon confidently dubbed it several times.

Blaikie Whitecloud echoed that sentiment.

“The Collaborative Housing Alliance is a generational project that’s starting now to change the housing landscape so that we can have more solutions and more opportunities for people to be stably housed.”

scott.billeck@freepress.mb.ca