The clan — now headed by the 72-year-old Galen Weston — consistently ranks as Canada's second wealthiest family, with an estimated net worth of $8 billion, according to Forbes.
Across the pond, Weston’s Irish-born wife, Hilary, rates No. 1 on the Emerald Isle's rich list and the family is among the Top 15 richest in the United Kingdom where they own food and fashion retailers.
Today, perhaps the most recognizable family member to the average Canadian is Weston’s son, Galen Weston Jr., also known as Galen G. Weston, who frequently appears in commercials for Loblaw grocery stores and President's Choice label foods.
But the family's empire in Canada dates back to the late 19th century. It grew out of the bread factory the elder Galen’s grandfather George Weston, established in Toronto, after his parents had settled in the city in 1868. That business prospered, becoming the country’s largest bread factory and the foundation of the family's wealth.
George’s second child, Garfield, took over after George's death in 1924. He entered the biscuit-making business but struggled after trying to expand into the U.S. just before the Wall Street crash.
In 1932, he used his few remaining funds to move the family back to the United Kingdom and buy up businesses there. There, he built the food processing and retailing company Associated British Foods into a multinational corporation that did business in the United States, Australia, South Africa and Ireland.
In the 1970s, the Weston empire was split among some of Garfield’s children. His son Garry took over the larger British end, while the youngest of nine children, Galen, was sent back to Canada to rescue the floundering Loblaw grocery chain, which the family took over several decades prior.
Back to Canada
At the time, Galen had been tending to other ventures in Ireland. Taking advantage of rock-bottom prices due to a bleak economy, he'd also purchased a number of stores and started Primark, what later became a large clothing retailer operating across Europe.
In 1966, he'd married 19-year-old Irish model Hilary Frayne. Together, the couple bought Ireland's Brown Thomas chain of department stores, driven in part by Hilary's love of fashion.
About five years after their marriage, the couple moved to Toronto to try to revitalize about 200 stores and subsidiaries in Canada for the family empire.
The Canadian arm of the Weston food-and-fashion empire flourished in the coming decades, expanding both domestically and back across the pond.
Today, Galen Weston is executive chairman of George Weston Ltd., one of North America's largest food processing and distribution groups.
The corporation oversees both grocery giant Loblaw Companies and Weston Foods, a baking manufacturer. Galen Weston also controls Selfridges Group. Its department store holdings include Canada's Ogilvy's and Holt Renfrew, Ireland's Brown Thomas, de Bijenkorf in the Netherlands and Selfridges in the U.K.
'You can't be passive'
His son, Galen Weston Jr., also nicknamed G2, took over the helm of Loblaw in 2005, while his daughter Alannah was appointed creative director in 2003 for Selfridges, the high-end British department store.
The family largely avoids the limelight, giving few interviews in the past decades.
In a rare interview with the Financial Times in 2011 with Galen Weston and daughter, Alannah, he acknowledged how difficult the retail environment has been during the recent global economic downturn.
"Shops are not a growing business so it's a scary place to be," Galen Weston told the newspaper.
"You have to constantly upgrade to keep making sure you're the best and the most exciting place to be," he added. "And you can't be passive. You have to stand — metaphorically — in the street and shout at people, wave at them, tell them how great you are and that if they come in they'll have a great time."
True to family form, Alannah has garnered attention while at Selfridge's.
She told the Financial Times she believes strongly in "retail activism," or using the shopping experience to educate customers and affect social change. At the department store, she launched a campaign to teach customers about the environmental dangers faced in the oceans.
It appears to be a philosophy shared by her brother.
After the Bangladesh factory collapse on Apr. 24 that killed more than 1,100 garment workers, Galen Weston Jr. vowed that Loblaw would stay in the poor South Asian country to affect change.
"Our priority is to do what's right for those affected by the tragedy," he said.- Joe Fresh vows to be 'force for good' in Bangladesh
The company's affordable clothing Joe Fresh brand had items made at the Rana Plaza factory that collapsed under the weight of illegally added floors.
Millions in donations
The Weston family is active in a number of philanthropic ventures, particularly in support of the arts. Hilary Weston, who served as Ontario's lieutenant-governor from 1997 to 2002, supports a number of charities influenced by her Irish heritage.
She founded the Ireland Fund of Canada, a non-partisan organization that finances projects in her mother country, and the Hilary Weston Writers' Trust Prize, Canada's richest prize for non-fiction.
Since the 1950s, the family has donated millions of dollars to a variety of causes through the W. Garfield Weston Foundation, named for the elder Galen Weston's father.
The family has made several large-scale donations, including $15 million to the Ontario Science Centre in 2003 and $20 million to the Royal Ontario Museum in 2004.
The family members rub shoulders with the elite across North America and in the United Kingdom. Galen Weston is known to play polo with Prince Charles and the Queen Mother stayed at their Toronto home when she visited the country in 1989.
Hilary and Galen Weston also own a housing development in Florida's Vero Beach and stay at Fort Belvedere, formerly the country home of King Edward VIII, when in Britain.
While Galen Weston Jr. gives off a boyish, average-Joe image in public, he, too, enjoys the family riches.
When he married Alexandra Schmidt, granddaughter of the Bata shoe mogul, Thomas Bata, in 2005, the pre-wedding party saw a Loblaws warehouse transformed with white carpeting, orchid chandeliers and waterfalls.
The same year, the Harvard- and Columbia-educated Weston inherited the executive chairman position at Loblaw at age 33 when the stock was struggling.
Loblaw, Canada's largest grocery store operator, oversees numerous supermarkets across the country, including No Frills, Provigo, Independent, Zehrs and Superstore.
Galen helped the company weather the economic downturn but it has experienced financial hurdles in recent years. With the arrival of Target in Canada and Wal-Mart's expanding food offerings, the company will face fierce competition in the future.
The $12.4-billion purchase of Shoppers Drug Mart brings additional health and pharmacy offerings to the ever-growing grocery-and-fashion empire.
It remains to be seen whether the acquisition will buffer it from encroaching rivals.- Loblaw's Shoppers Drug Mart bid escalates grocery warsLoblaw to buy Shoppers Drug Mart for $12.4B Suggest a correction