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5 Torontonians who cracked Maclean’s richest Canadians list

Maclean’s has released a round-up of the 40 wealthiest Canucks, and a fair share of rich Torontonians made the cut
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Toronto skyline as seen from the Cape Avenue pedestrian bridge.

Torontonians including Loblaw chairman Galen Weston Jr. and Mattamy Homes founder Peter Gilgan are among the richest people living in Canada.

It’s been seven years since Canadian Business stopped publishing its list of the 100 richest Canadians — now, Maclean’s is here to revive the project. 

The Canadian current affairs magazine released a round-up of the 40 wealthiest Canucks last week and a fair share of Torontonians made the cut. 

Maclean’s reports its "extensively researched” list is the “definitive ranking” of rich Canadians. Its wealth estimates come from sales data, insider trading reports, SEC filings and industry comparisons.

Here’s a look at the top 5 wealthiest Torontonians that made the list, how much they’re worth and how they made their fortunes.

The Thomson family

Rank: No. 1

Estimated net worth: $98.15 billion

It’s no surprise to see the Thomson family top Maclean’s list of richest Canadians. According to Forbes, they’re the fifth richest family in the world, behind the billionaire families that own LVMH (the Arnaults), Walmart (the Waltons), L’Oréal (the Bettencourt Meyers) and the bulk of Mexico’s telecommunications (the Slims). 

The Thomson family's wealth comes from their media empire, started by Roy Thomson, the 1st Baron Thomson of Fleet. Roy was born in Toronto and bought his first newspaper, the Timmins Daily Press, in 1934.

He moved to the U.K. and expanded his holdings to include properties in publishing, printing and television, becoming so successful that he was elevated to the peerage, making him a literal media baron. 

The current patriarch of the Thomson family, David, was also born in Toronto like his grandfather Roy and his father Kenneth. In 2008, David acquired the newswire Reuters and became the chairman of the since merged Thomson Reuters.

The family also owns The Globe & Mail and holds stakes in Bell Canada, the Winnipeg Jets and the Montreal Canadiens.

Galen Weston Jr. 

Rank: No. 3

Estimated net worth: $18.05 billion

Galen Weston Jr. needs no introduction for the millions of Canadians who shop at Loblaw-owned grocery stores. Like David Thomson, Galen inherited his business holdings from an enterprising ancestor — his great-grandfather George Weston — who founded George Weston Ltd. in 1882.

What began as a modest bread business in Toronto eventually grew into the largest supermarket retailer in the country. Today, George Weston Ltd. controls Loblaw Companies, which owns brands like President’s Choice, No Name and Joe Fresh as well as retailers like No Frills, Shoppers Drug Mart and Fortinos.

Galen was the company spokesperson of Loblaw for a time but increasingly became referred to as the “face of grocery store gouging” during a surge in food inflation throughout the COVID-19 pandemic.

He has since stepped down as president of Loblaw and was succeeded by Per Bank, a Danish retail executive, in 2024. 

The Rogers family

Rank: No. 7

Estimated net worth: $12.47 billion

Starting with just one Toronto radio station, late family patriarch Ted Rogers created a telecommunications and media empire. Today, Rogers Communications provides phone, television and internet services across the country and owns dozens of television and radio stations, including CityNews, OMNI and Sportsnet.

Through Rogers Communications, the Rogers family also owns the Toronto Blue Jays and a large stake in Maple Leaf Sports & Entertainment (MLSE). 

Despite Rogers Communications remaining, at its heart, a family company, the Rogers household has seen its fair share of drama. After Ted’s death, eldest son Edward Rogers III became chair of the family trust, kicking off a Succession-like battle for control over the keys to the kingdom. 

The Apostolopoulos family

Rank: No. 13

Estimated net worth: $9.4 billion

The Apostolopoulos family control a vast portfolio of commercial properties acquired by the late Andreas Apostolopoulos, who immigrated to Canada from Greece in 1969. He was a labourer before starting an office-cleaning business, followed by a plastic bag manufacturing firm.

Eventually Andreas found his way into commercial real estate and founded the Triple Group of Companies in Toronto. 

His sons Steve, Peter and Jim now preside over the company, whose holdings include Durham Live, a 240-acre entertainment destination being developed in Pickering, Ont., and Toronto’s TriBro Studios, which provides filming locations for Disney, Netflix and Bell Media.

Peter Gilgan

Rank: No. 16

Estimated net worth: $8.64 billion

Peter Gilgan is the billionaire owner and founder of Mattamy Homes, Canada's largest residential home builder. 

According to Macleans, Mattamy has built over 135,000 homes since it was founded in 1978. 

Gilgan started the company in Toronto and named it a portmanteau of his two oldest children’s names, Matthew and Amy. 

Most of the homes built by Mattamy are located in the Greater Toronto Area, but the company also has projects in Alberta and the U.S. In 2011, Peter Gilgan donated $15 million to Toronto Metropolitan University and the money was used to create the Mattamy Athletic Centre at Maple Leaf Gardens. 

Other Torontonians that made the Maclean’s Rich List include Mark Scheinberg, who co-founded PokerStars; Stephen Smith, who co-founded mortgage lender First National Financial; Mark Leonard, a venture capitalist and founder of Constellation Software; and Leonid Boguslavsky, a venture capitalist and tech founder who once worked at the University of Toronto. 

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