Family-owned companies play a pivotal role in shaping the economic landscape of Canada, contributing more than $500 billion to the nation’s GDP. They account for two-thirds of private-sector companies and employ nearly 7 million people—approximately 47% of all private-sector jobs. Notably, Toronto, as Canada’s largest city and financial hub, is home to five of the country’s top 10 highest-earning family businesses. From food giants to tech innovators, these family-run enterprises have become cornerstones of the local and global economy.
In this article, let’s look closer at Toronto’s 10 Largest Family Businesses, showcasing the entrepreneurs and families behind these economic powerhouses.
Owning Family: Weston
Annual Revenue: $43 billion
Founded in 1882 by George Weston, this company started as a small bread route and has since grown into one of Canada’s largest and most influential family-owned businesses. Today, George Weston Ltd. operates through its two major segments: Loblaw Companies Limited, Canada’s leading food and drug retailer, and Choice Properties REIT, the nation’s largest diversified real estate investment trust.
With over 200,000 employees across its various segments, George Weston is a cornerstone of Canada’s retail, food, and real estate industries. The family continues to lead with Galen G. Weston, great-grandson of the founder, at the helm as Chairman and CEO.
Owning Family: Stronach
Annual Revenue: $40.5 billion
From humble beginnings as a small machine shop, Magna International has evolved into one of the world’s largest automotive suppliers. Founded by Frank Stronach in 1957, the company is a key player in automotive components, including exteriors, interiors, powertrains, and electronics. Magna operates 351 manufacturing facilities and 103 product development centers in over 30 countries.
Stronach’s entrepreneurial spirit and vision have made Magna an industry leader, and despite stepping down from day-to-day operations, he still holds significant voting rights, maintaining his role as honorary chairman.
Owning Family: Watsa
Annual Revenue: $30.7 billion
Fairfax Financial, founded in 1985 by Prem Watsa, operates in property and casualty insurance, reinsurance, and investment management. Through a strategic acquisition model, Fairfax has become one of the leading global commercial insurance groups, with a diverse investment portfolio that includes companies like Occidental Petroleum, Blackberry, and Micron Technology.
Prem Watsa continues to serve as Chairman and CEO, with his son, Benjamin P. Watsa, also active in the company as a board member.
Owning Family: Billes
Annual Revenue: $13 billion
What started as a modest tire shop in 1922 has grown into one of Canada’s most beloved retail brands. Founded by brothers J.W. and A.J. Billes, Canadian Tire now boasts over 1,700 locations across the country. The company’s diversified business model includes automotive products, hardware, sporting goods, and financial services.
The Billes family continues to play a key role in the business, with Martha Billes and her son Owen Billes serving on the company’s board of directors.
Owning Family: Rogers
Annual Revenue: $12 billion
With a history dating back to 1960, Rogers Communications was founded by Ted Rogers as a small radio station. Over the decades, the company has grown into a media and telecommunications giant. Rogers is a leader in Canada’s wireless and cable industries and owns the country’s only Major League Baseball team, the Toronto Blue Jays.
Rogers continues to be a family-controlled business, with Edward S. Rogers, Ted’s son, serving as Chairman of the Board.
Owning Family: McCain
Annual Revenue: $8 billion
Founded in 1957 by brothers Wallace, Harrison, Robert, and Andrew McCain, McCain Foods has become the world’s largest producer of frozen French fries, with a global network of 51 production facilities. From its early days as a small Canadian family farm operation, McCain Foods has expanded into a global leader, selling in over 160 countries.
Scott McCain, son of founder Wallace McCain, serves as Chairman, continuing the family’s legacy of global success.
Owning Family: Leonard
Annual Revenue: $7.5 billion
Founded in 1995 by Mark Leonard, Constellation Software specializes in providing software and services across industries such as healthcare, education, and real estate. The company has grown rapidly, acquiring multiple software companies and building a portfolio of market-leading products. Constellation’s strategic approach to acquisitions has positioned it as a global powerhouse in vertical market software.
Mark Leonard continues to guide the company as its president, ensuring its ongoing growth and success.
Owning Family: Thomson
Annual Revenue: $6.7 billion
Originally founded by Roy Thomson in the 1930s as a newspaper business, Thomson Reuters has evolved into a leading provider of data and information services in legal, tax, accounting, and media. The company’s reach extends globally, with its content used by professionals and organizations across the world.
Currently, the company is chaired by David Thomson, the founder’s grandson, who continues to oversee its expansion and diversification into new markets.
Owning Family: Samuel
Annual Revenue: $5 billion
Samuel, Son & Co., North America’s largest family-owned metal distributor, traces its origins back to 1855 when brothers Mark and Lewis Samuel started a hardware and metals import/export business. Today, the company operates 18 businesses with over 5,000 employees across Canada, the US, and Mexico, supplying metal products to industries like aerospace, automotive, construction, and energy.
Family members Mark, Kim Samuel, and Rick Balaz are equal owners, maintaining control of this 170-year-old conglomerate.
Owning Family: Hennick
Annual Revenue: $4 billion
Founded in 1898, Colliers International started as a Canadian real estate and insurance agency. Over time, the company expanded globally, becoming a leading commercial real estate service provider with 522 offices in 62 countries. Under the leadership of Jay Hennick, the company has diversified into real estate management, investment, and hospitality consulting.
Hennick, who is also the company’s CEO, continues to guide Colliers through its global expansion and innovation.
Why Family Businesses Matter to Toronto and Beyond
These Toronto-based family businesses are not only significant players in Canada’s economy but also shape global industries through innovation, investment, and strong leadership. Family-owned enterprises have proven to be resilient and adaptable, ensuring their continued success across generations. Whether in retail, technology, manufacturing, or finance, Toronto’s family businesses remain at the heart of Canada’s economic prosperity.
With such a rich legacy of entrepreneurship, Toronto will continue to be a hub for both traditional and innovative family-run businesses, contributing to the city’s dynamic growth and its global reputation as a center of commerce and technology.
