Jon Harstone, a pillar of the affordable housing community in Toronto, had extraordinary instincts about the skills and connections necessary to reach the common end goal.

On New Year’s day, the housing sector in the Greater Toronto Area got dealt a blow with the sudden death of leading affordable housing developer, Jon Harstone.

Born in 1950, Harstone came of age in the 1970s when affordable housing development was firmly on the federal government’s radar. He bragged that the Canadian Mortgage and Housing Corporation (CMHC) distributed millions of dollars to a young guy like him to see what he could do with the money – and he ended up doing great things.

Brian Iler, founding partner of Iler Campbell, delivered a tribute at Jon’s retirement party in 2019, where he described Jon’s countless housing projects including his founding of St. Clare’s Multifaith Housing. St. Clare’s repurposes urban properties into housing for people experiencing homelessness or precarious housing.

At the party, we also celebrated Local 75 Hospitality Workers Housing Co‑operative, one of the rare new‑build and green housing co‑ops in downtown Toronto. Local 75 was the brainchild of Pam McConnell, a housing co‑op stalwart who held a downtown council seat from 1994 until her death in 2017. Pam and Jon were the only people who truly understood the complexity of the project, taking much of that expertise with them at their untimely deaths.

While Jon may have formally stepped away in 2019, he never retired.

Federal funds for affordable housing came to a screeching halt in 1993. Just two years later, with the election of Harris’ Progressive Conservatives, provincial funding was severed. Jon recognised, in addition to limited governmental funding, Ontario lacked opportunities for young people to learn the art and skill of housing development. One of Jon’s most significant roles was as mentor to a new generation of housing developers — a labour of love that continued until his death.

Anjala Kulasegaram, a mentee working with Jon in the months before he died, admitted she largely took her role at the Co‑operative Housing Federation of Toronto (CHFT) because she was promised mentorship from the legendary Jon Harstone. Now in her thirties, Kulasegaram was raised in Scarborough’s Woburn Village Co‑op, making her eligible for a Diversity Scholarship that financed her post‑secondary education. She can likely recite the Co‑operative Principles that underpin the co‑op movement, backwards.

Even if CMHC were still in the business of large-scale development from the ground up, Kulasegaram knows the current focus on accountability for public funds means it is unlikely someone her age would be entrusted with a multi‑million dollar budget to build affordable housing. Yet she felt with Jon’s support, she would develop the confidence to take the risks he did 45 years ago.

Kulasegaram reports a close and meaningful mentorship from Jon. He taught her that the modern fixation on protecting existing stock and adding the table scraps from for‑profit developers, will not meaningfully alter the affordable housing landscape. Jon encouraged her to feel entitled to stand alongside big‑money developers and fill her plate at the housing buffet. He felt it was the only way to get affordable, safe, and permanent housing for all.

Harstone did not talk much about his successes but his mentor learned from the scary situations he encountered along the way. Jon was a whiz with numbers; Kulasegaram wishes she could still learn from his analysis of the messy, unaligned programs and patchwork approach to housing. He had extraordinary instincts about the steps, skills and connections necessary to reach the common end goal. For Kulasegaram, Jon’s death leaves a gaping hole in her professional development and she worries how she can fill it, knowing there are so few around who have similar experiences to him.

Anjala Kulasegaram is the last of Jon’s many mentees. James Calderone first encountered Jon’s generosity as a student. They reconnected later when Calderone joined Homestarts, a property management company with roots in co‑op development. Like Kulasegaram, Calderone mostly heard about the challenges; Jon recognised mistakes are the best teachers. Calderone remembers witnessing “a heavyweight bout of words” between Jon and Nancy Singer, another developer of Jon’s generation, when the two talked housing. Singer died in 2021 — another loss to the housing development world.

The bouts of words Jon used were not the most carefully chosen but he was clear and passionate about moving the needle on housing. Another one of Jon’s mentees, heard him say to an indecisive affordable housing provider: “if you don’t fucking take these units [from the developer], we’ll find someone else who will.” That’s the kind of confidence, conviction, and forthrightness that makes for great learning.

I am not the only one worried about this generational gap.

The Canadian Housing and Renewal Association (CHRA) is a national umbrella organization for housing. Established in 1968, they support the social housing sector to ensure all Canadians have access to affordable, secure, and decent housing. CHRA knows the sector’s struggle to attract and maintain a new generation of professionals. The Association developed the Housing Professionals Mentorship Program in partnership with the Housing Partnership Canada and the Chartered Institute of Housing Canada. They consulted Jon in the early stages of the program’s development, knowing he would embrace the idea of development leadership competencies among housing professionals.

Jake Gorenkoff, a director at CHRA, proudly told me the mentorship program is in its fifth year, counting over 220 people involved as mentors and mentees. The program aims to be self‑sufficient soon, relying on a combination of sponsorship and user fees for participants who can afford it (they offer bursaries for those who cannot).

Gorenkoff confessed they do not receive as much interest in development as he would like; many of the mentor/mentee relationships are focussed on learning about the management of existing properties. He lamented the fact the sector is not attractive to those with aspirations in housing development.

Another Homestarts alumnus, Patrick Masterson, is now a housing development consultant who works with Tim Welch Consulting (TWC). The firm helps clients achieve their affordable housing goals through research, planning, and development services. Masterson left me more hopeful when he told me that of TWC’s office of 12, nine are under the age of 40.

But the generational gap remains a real concern. Why?

Low salaries are part of the answer. The very housing crisis we are trying to solve pushes younger people, eager to achieve home ownership, to sacrifice working where their passions lie for the premium of working in the for‑profit sector.

Perhaps our current challenge is less about losing the Harstones and the Singers and the McConnells, and more about having to navigate an increasingly complex regulatory environment that stifles the kind of creativity developers brought to the table over the last 40 years.

CMHC, provincial housing ministries, and local governments: the current system is not working. Offer housing incentives attractive to a new generation of developers to create vibrant, safe, secure, and affordable communities for all.