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For the Diamonds, giving back is a family affair

The four Diamond brothers say philanthropy has helped make an already close family even closer

The Diamond family’s philanthropic journey began with parents Ephraim and Shirley, who started out with nothing in the wake of the Second World War, at a time when being Jewish was too often met with trauma, rejection and sometimes violence. In 1953—with determination, resilience and “a lot of luck,” as Ephraim, universally known as “Eph,” would say—he founded Cadillac Development Corporation, which went on to become one of North America’s premier real estate developers as Cadillac Fairview Corp. 

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From a young age, Eph and Shirley’s children were encouraged to reach their potential through education and hard work. In the early 1990s, Carey Diamond created Whitecap Venture Partners to refocus the family’s investments into growing technology businesses; it is now one of Canada’s longest-standing successful venture funds. Stephen Diamond, after practising municipal law for decades, became the President and CEO of DiamondCorp, a Toronto-based land development company that is engaged in acquiring and developing real estate in Canada. Michael Diamond has been a teacher, lawyer, technology CEO and business consultant and investor, while Mark Diamond has been involved in technology and real estate, was until recently the co-owner of a successful Ontario summer camp, and is now a life coach. 

Eph and Shirley Diamond raised a closeknit family and taught their children the power of philanthropy. The family are long-term supporters of several organizations, including the Hebrew University, UJA of Greater Toronto, Sunnybrook Health Sciences Centre, Ve’ahavta, Leave Out Violence, Baycrest Centre, United Way and many others.

Here, the Diamond brothers collectively share their family’s history of wealth stewardship, their advice for encouraging philanthropy among today’s youth, and their determination to promote equal rights among all humans, beyond religious or spiritual differences.

What has been your family’s philanthropic journey and how did previous generations inspire you to develop your philanthropic initiatives?

We remember hearing stories about our immigrant grandparents, who were extremely poor but always put a little money away each week from their paycheques even though they could have used every penny. Many Jewish immigrants at that time had something called a ‘Pushkah’ jar, which was a Yiddish name for a charity jar where you put in 10 per cent of your earnings for others. Even though our grandparents were extremely poor, this value system was something that was instilled in our parents. 

Our parents then encouraged us at a young age to give to those in need and get involved in helping others. They said the greatest gift of having financial security was that you could give to others.

They taught us that money could not buy happiness, but that giving money to others or, more importantly, giving your time to charitable initiatives was actually a selfish act because it made you feel so good in doing so.

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As we entered our 20s and 30s, our philanthropic processes became more structured, and we held family meetings with our parents every quarter where the four sons, with our parents, would discuss what charities we wanted to support and why. This in turn strengthened the family bonds while also doing good for others.

It was also a given, and has been to this day, that if any one of us gets personally involved in a charity by sitting on its board or giving a lot of our direct time to the charity, then all of us would support that charity since we knew first-hand that we had input into how the charity was being directed.

Why has healthcare been important for your family to support in Canada?

Over 25 years ago, we identified healthcare as an important recipient of both our time and our charitable dollars. We believed there was an opportunity for us and other like-minded philanthropists to invest our time and capital to help bring Canadian hospitals into the top tier in the world in patient care, research and education. Given the nature of socialized medicine in Canada, we knew this was a challenge, but one worth addressing given the magnitude of the importance of good healthcare for Canadians.

Our parents made it clear to us that as society has been good to us, it was extremely important for our family to give back to the community

The Diamond brothers

In Canada, tax dollars represent the bulk of the funding for provincial healthcare. But charitable giving is critical to improve outcomes, as the tax dollars are never sufficient. By putting in our time (as board and committee members) and our dollars towards specific initiatives, we knew we could make a difference.

Both Carey and Steve, and most recently Steve’s wife, Karen Diamond, have been involved at the board and committee levels of Sunnybrook Health Sciences Centre and the Sunnybrook Foundation, and they have helped drive specific, important initiatives such as the Garry Hurvitz Brain Sciences Centre and improved cardiology procedures. In addition, Carey spent a decade on the board of Baycrest Centre, helping Baycrest dramatically improve seniors care in the province. Mark today remains on the board of that organization’s foundation. We have also donated lesser amounts of time and dollars to Mount Sinai Hospital and Toronto General Hospital for specific initiatives.

Have there ever been differences in passions or challenging moments in your philanthropic journey that required advisors or guidance among family members?

Unlike many foundations, our family’s giving started with two generations and six sources of funds: our parents, Eph and Shirley, and each of four brothers. In fact, the approach taken was somewhat unique in that we used the opportunity to both give together and individually as part of our overall approach to using philanthropy to build stronger family relationships.

At the outset, we create a budget for the family giving that would be done together. That budget is then subdivided such that each individual is allocated a specific amount from the budget to donate. In addition, a portion of the total budget is allocated to funding on a joint basis—that is, all four brothers would agree to that funding. Some of these are more substantial longer-term donations, which we call Foundational Gifts. One of the largest of those Fondational Gifts is to Sunnybrook Health Sciences Centre.  

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As a result of this carefully designed process, we were able to allocate funds for donation purposes for each individual while carving out a significant portion of the budget for foundational investments, as well as designating funds that we would agree to allocate annually together.

The need to decide on the foundational gifts and the joint allocations has always been a major source of discussion, and indeed there are often different philosophies expressed around the table. Yet the process of exploring those differences, explaining them, sharing them and then resolving them has not only worked well in terms of our philanthropy, but also brought the family closer together in the process. Philanthropy has been a positive family-builder as opposed to a challenge, despite four brothers who are different in many ways but share a common desire to help others and the broader society.

How do you involve children and/or grandchildren as they grow to understand wealth stewardship and giving back?

The four Diamond brothers are actually the beneficiaries of exactly the process that we believe should be incorporated by all our families. The question now is how to move that to the next generation as our children are now mostly married and have careers of their own. 

As we grew into our teenage years, our parents made it clear to us that as society has been good to us, it was extremely important for our family to give back to the community. Similarly, all of our (collectively 13) children grew up learning from us by example, as all of us have not only made direct financial gifts but have also given of our time to many charities. As our children saw and were involved informally in what we were involved with, they learned the importance and personal value of charitable giving. We are currently involved, in each individual family, in moving the traditions of our parents to the next generation using many of the same processes as we had the benefit of using with our parents.

For those families who might feel nervous about approaching their own second and third generations about the idea of wealth stewardship, do you have any advice for approaching those conversations?

Begin the process at a young age by modelling the behaviour you recommend, and also by teaching your children your own philosophy of family giving. As your children become older, having regular family meetings is a great way to ensure this important value stays at the forefront and allows for reflection and growth in how your family approaches philanthropy. Share what you do and what you give openly, and share as well the reasons why and the benefits of doing so.

Can any of you share any upcoming initiatives or projects that you’re excited about?

It’s important for us to contribute our time and donation dollars to both secular and Jewish charitable causes. Karen Diamond has recently become Co-Chair of the 2025 UJA campaign. Steve has joined Mike on the UJA Federation Board, and Mike has become Co-Chair of the Jewish Foundation as well.

Due to recent events, a major focus of ours has been on both combating the major resurgence in antisemitism and ensuring the safety of Jewish institutions and those that frequent them. The family is also highly focused on improving relationships among Jewish and Arab Israelis through Mark Diamond’s involvement in Heart to Heart, which brings Jewish and Arab Israeli teenagers to summer camp in Ontario to learn more about one another and develop bonds of friendship. This initiative complements a major endowment at the Hebrew University that supports both Arab and Jewish Israelis in their educational journeys.

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The family continues to support Save a Child’s Heart, which was launched in Toronto by our late father. It supports life-saving heart surgery in Israel for children from neighbouring impoverished regions, especially from the West Bank and Gaza (in better times) and in Africa. 

In addition, there are exciting new projects at Sunnybrook, yet to be announced, which the family is working on in earnest that will transform healthcare for Canadians. 

Each of us are heavily involved in many other opportunities in the philanthropic space which ebb and flow over time, and we spend a good deal of time sharing with each other what we are involved with. We are a close family, made even closer by our common interest in making the world a better place through philanthropy.

For us, philanthropy is the gift that just keeps giving!  

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