Toronto’s 10 Largest Family Businesses 

Toronto Skyline

Family enterprises are a driving force in Canada’s economy, accounting for two-thirds of private-sector companies and contributing over $500 billion to the nation’s GDP. Family-owned businesses are responsible for around 47% of Canadian private sector jobs, employing 6.9 million people. Canada’s largest family firms contribute nearly $200 billion to the country’s GDP alone.

Toronto is Canada’s largest city, its financial and commercial hub, and home to North America’s third-largest stock exchange, the TSX. Thanks to a strong entrepreneurial spirit, five of Canada’s top 10 highest-earning family businesses can be found in Toronto. The city also boasts the nation’s largest family offices and focuses its investments on innovation, which has created a thriving technology sector. Toronto’s 24,000 tech companies have helped the city become the third-largest technology centre in North America.

Here are the 10 Largest family businesses in the Greater Toronto Area: 

Colliers International
Image via Shutterstock

10. Colliers International Group Inc.  

Owning/Controlling Family: Hennick  

Annual Revenue: $4 billion 

The commercial real estate service provider’s history dates back to 1898 with the founding of Canadian real estate, property management, and insurance agency, Macaulay Nicolls. In 1984, Macaulay Nicolls Maitland joined with Australia’s Colliers International to form a global real estate services organisation. Leading property management and hospitality consulting firm FirstService partnered with Colliers in 2004, eventually transforming into Colliers International Group Inc. in 2015, along with the company’s global brands. 

Colliers International operates 522 offices in 62 countries. Jay Hennick is the company’s global chairman, CEO, and controlling shareholder. 

Samuel Office
Image via Shutterstock

9. Samuel, Son & Co.  

Owning/Controlling Family: Samuel  

Annual Revenue: $5 billion 

North America’s largest family-owned processor and distributor of metal products and solutions, Samuel, Son & Co., began as a hardware and metals import/export business founded by brothers Mark and Lewis Samuel in 1855. Today, the company operates a group of 18 businesses whose fabricated components can be found in industries including aerospace, agriculture, automotive, chemicals, construction, energy, food & beverage, infrastructure, rail, transportation, and mining. 

Family members Mark Samuel, Kim Samuel, and Rick Balaz are the equal owners of the 170-year-old conglomerate. Samuel, Son & Co. operates over 80 locations across Canada, the US, and Mexico, with over 5,000 employees. 

Thompson Reuters
Image via Shutterstock

8. Thomson Reuters Corporation  

Owning/Controlling Family: Thomson  

Annual Revenue: $6.7 billion 

The media conglomerate began as a single Canadian newspaper acquired by Roy Thomson in the 1930s. Thomson Newspapers expanded overseas during the 1950s, acquiring UK national and regional newspapers, including The Sunday Times, making the company Canada’s largest newspaper owner. Throughout the 1990s and early 2000s, Thomson divested in its newspaper business, including selling one of Canada’s largest daily newspapers, The Globe and Mail, to the Thomson family’s investment vehicle, The Woodbridge Company, in 2003. In 2008, The Thomson Corporation and Reuters Group PLC combined to form Thomson Reuters. 

Today, Thomson Reuters Corporation provides data and information services across 3 different industries: legal, tax and accounting, and news and media. The company’s content has become widely used by broadcasters, publishers, governments, advertisers, tax and Legal professionals, and media outlets. David Thomson, the founder’s grandson, serves as Thomson Reuters’s chair.

Constellation Software
Image via Shutterstock

7. Constellation Software

Owning/Controlling Family: Leonard  

Annual Revenue: $7.5 billion 

Constellation Software provides software and services to the global marketplace across sectors that include agri-business, education, healthcare, real estate, construction, and hospitality. The company’s strategy is to gain, manage, and grow software businesses that address the critical needs of specific industries. Since its founding in 1995, Constellation has amassed a portfolio of software companies with the potential to become market leaders. Constellation operates six service groups that provide tailored software solutions to customers in over 100 international markets. 

After working as a venture capitalist, Constellation Software founder Mark Leonard built his vertical software company using an investment, reinvestment, and allocation approach similar to Berkshire Hathaway but focussing on completely different industries. Mark Leonard directs Constellation’s activities as the company’s president.   

McCain Foods
Image via Shutterstock

6. McCain Foods Ltd.

Owning/Controlling Family: McCain  

Annual Revenue: $8 billion 

McCain Foods is the world’s largest manufacturer of frozen French fries, selling in over 160 countries with a food production network of 51 facilities. Around the world, 1 of every 4 fries is a McCain Foods fry. The global food brand also operates prepared potatoes, appetisers, potato seed cultivation, transportation, and food services segments. 

Brothers Wallace, Harrison, Robert, and Andrew McCain combined their family’s farming knowledge with innovative frozen food technology to produce frozen French fries in 1957. McCain Foods became a leader in the Canadian marketplace before entering the UK, Europe, and Australian markets during the 1960s and 1970s. The company continued to expand its global footprint and product offerings through acquisitions, including Anchor Food Products in the US, leading Chinese entrée manufacturer Wing Wong Foods, and the Netherlands’ CelaVita Foods. Scott McCain, son of founder Wallace McCain, serves as the company’s chairman. 

Rogers Store
Image via Shutterstock

5. Rogers Communications Inc.  

Owning/Controlling Family: Rogers  

Annual Revenue: $12 billion 

Ted Rogers built the radio station he purchased with a small loan in 1960 into a media and communications empire. Rogers pioneered Canadian cable television services during the 1970s and developed one of the country’s leading cellular networks in the 1980s. Today, the company’s wireless network is one of Canada’s most extensive, with the ability to deploy LTE services to approximately 96% of the nation’s population. Rogers was Canada’s first telecommunications company to commercially offer 5G as a network technology. 

Rogers’ media segment provides sports and entertainment, including exclusive National Hockey League broadcast licensing. The company also owns Canada’s only Major League Baseball team, the Toronto Blue Jays. Ted Rogers’ son, Edward S. Rogers, serves as chair of Rogers Communications

Canadian Tire
Image via Shutterstock

4. Canadian Tire Corp Ltd.  

Owning/Controlling Family: Billes  

Annual Revenue: $13 billion 

Brothers J.W. and A.J. Billes bought a Toronto tire shop and garage in 1922. A year later, the brothers moved and renamed their business the Canadian Tire Corporation. The company opened its first franchise location in 1934, establishing its highly successful expansion model. Canadian Tire launched its gas bar business in 1958 and introduced its iconic coupons, later known as Canadian Tire money, in 1961. By the early 80s, Canadian Tire’s footprint extended across the country. The company entered the financial services sector a decade later and opened its own banking business in 2003. 

Canadian Tire is one of Canada’s most respected general merchandise retailers, with 1700 locations nationwide. The company also operates 13 separate retail and services banners and 16 consumer brands. Martha Billes, daughter of founder A.J. Billes, sits on Canadian Tire Corporation’s board of directors along with her son, Owen Billes. 

Blackberry Office Sign
Image via Shutterstock

3. Fairfax Financial Holdings Ltd.  

Owning/Controlling Family: Watsa  

Annual Revenue: $30.7 billion 

Fairfax Financial Holdings Limited primarily operates through its subsidiaries in property insurance, casualty insurance, reinsurance, and investment management. Founded in 1985 by Prem Watsa, the company grew through an acquisition strategy that helped Fairfax become a leading global commercial lines insurance and reinsurance group. The firm’s investment portfolio holds significant positions in companies including Occidental Petroleum, Blackberry Ltd., and Micron Technology Inc. 

Prem Watsa serves as Fairfax Financial’s chairman and chief executive officer. His son, Benjamin P. Watsa, sits on Fairfax’s board and is the founder and chief executive officer of Marval Capital Ltd. 

Image via Shutterstock

2. Magna International  

Owning/Controlling Family: Stronach  

Annual Revenue: $40.5 billion 

After dropping out of school at age 14 to become a tool and die maker, Frank Stronach grew the small machine shop he opened in 1957 into one of the world’s largest automotive suppliers. Originally named Multimatic, Stronach’s company received its first General Motors parts contract to produce metal-stamped sun visor brackets in 1959. Over the next decade, the company opened additional manufacturing facilities and merged with its Magna Electronics Corporation segment in 1969. Magna expanded its parts offerings to plastics and developed its popular RIM bumper process in the early 1980s. The company secured a landmark contract to supply automotive sheet metal for American Motors in 1985. 

Today, Magna International’s group of companies provides an extensive range of automotive components and solutions, including exteriors, interiors, powertrains, and electronics. The company’s global network includes 351 manufacturing operations and 103 product development, engineering and sales centres across 30 countries. Frank Stronach maintains most of Magna’s voting rights and is its honorary chair.  

Loblaws Store
Image via Shutterstock

1. George Weston Ltd. 

Owning/Controlling Family: Weston  

Annual Revenue: $43 billion 

In 1882, George Weston began his journey from working a single bread route to becoming Canada’s biggest baker, laying the foundation for the family’s food empire. Today, George Weston Limited operates through its two segments, Loblaw Companies Limited, Canada’s largest food and drug retailer with over 2400 locations, and Choice Properties Real Estate Investment Trust, the country’s largest diversified REIT. 

With over 200,000 working in its operating segments, George Weston’s group of companies is one of Canada’s largest private sector employers. The company’s Loblaw retail banner also provides banking services and fashion and owns four of Canada’s top consumer brands: President’s Choice, Life Brand, no name brand, and Farmer’s Market. 

Galen G. Weston, great-grandson of founder George Weston, leads his family’s enterprise as its chairman and chief executive officer of George Weston Limited and chairman of Loblaw Companies Limited.