
On November 19, the most sought-after pieces of the Hudson’s Bay Company’s massive trove of art and artifacts will be auctioned off in what may be the most high-profile art auction in Canadian history. Founded in 1670 as an English trading monopoly over roughly a third of what is now Canada, the Bay was the continent’s oldest corporation. It was also one with a tendency to self-mythologize: over the years, the company commissioned Canada’s finest artists to immortalize scenes of the country and the Bay’s place within it. We spoke with David Heffel, whose gallery is leading the auction, to hear about his five favourite pieces—and what he thinks they’ll go for.

Frederic Marlett Bell-Smith, “Lights of a City Street,” 1894, oil on canvas
This enormous oil painting is nearly two metres tall and depicts Toronto’s King Street West on a rainy 1890s day—the steeple of St. Andrew’s Church can be seen in the background. “You feel like you can step over the frame into the painting,” says Heffel.
Frederic Marlett Bell-Smith was an English-born painter commissioned to depict scenes of the young country from coast to coast as a way to build a sense of Canadian identity. Here, he does so by capturing cosmopolitan life in the city, and the result, says Heffel, is the painter’s “undisputed finest work.”
“It’s great to see the streetcars, and the details go all the way to the advertisements on the buildings in the background,” says Heffel. “It’s an arresting painting. If you walk by, it’ll stop you.”
Estimate: $100,000 to $150,000
Related: The Bay’s art collection is being auctioned off

Winston Churchill, “Marrakech,” circa 1935, oil on canvas
Yes, that Winston Churchill. In addition to being a legendary statesman, the wartime British prime minister was also an accomplished painter. His canvases are hot items in the art world: a painting he once gifted to US president Franklin D. Roosevelt was later purchased by Brad Pitt, only to be sold by Angelina Jolie for over $11.5 million (US) following the couple’s divorce.
While this Churchill hasn’t been handled by such celebrated hands, it’s still an important one. Capturing a serene scene in sun-drenched Morocco, it was painted in 1935, as Churchill was travelling across North Africa on an interwar holiday. In 1954, after the statesman retired from politics, he was given the honorary title of—take a deep breath—Grand Seigneur of the Company of Adventurers Trading Into Hudson’s Bay. The catch? The company asked for a painting in return. Churchill’s wife, to whom he had gifted his collection, decided that this one met the bar for donation.
Heffel’s estimate for the price doesn’t come close to reaching the sum fetched by Jolie, but he’s optimistic nevertheless. “It’s perhaps the top Churchill painting in the private domain,” he says. “We hope it’ll be a blockbuster.”
Estimate: $400,000–$600,000
Related: Billionaire David Thomson wants to outbid Galen Weston for the Hudson’s Bay charter

Painted by famed Canadian watercolourist Walter Joseph Phillips, this woodblock print captures the essence of the early HBC: Indigenous and European traders plying wares across the waterways of northern Canada. Pictured here are York boats, vessels specialized for river travel and typically helmed by Métis boatmen.
By the time Phillips painted this scene, in 1928, these boats had been replaced by steamships and rail lines. Therefore, says Heffel, this is a romantic image, based on memories of the boatmen reimagined in high-definition. “You can see the facial hair of the characters, the folds and creases in their clothes, the ripples and reflections of the water.”
Also present, says Heffel, are the “iconic Phillips clouds,” which are prized by collectors. “I don’t want to jinx it,” says Heffel, “But I think we’re going to set a record for a watercolour by him.”
Estimate: $15,000–$25,000

Adrien Hébert, “Christmas at Morgan’s,” circa 1936–1937, oil on canvas
This classic scene of Christmas displays isn’t the HBC at all: it’s a 1930s Montreal storefront of Morgan’s, the first department store in Canada, which was acquired by the Bay in 1960.
“Hébert is well-known for his Montreal street scenes, and this fits very well into his repertoire,” says Heffel. “Canadian art history is primarily landscape painting, so it’s special to see an urban scene filled with people—I like the little scotty walking in the foreground.”
It’s also a preview of the auction itself: after this piece and the other paintings are auctioned off, a wider online auction will see window displays like the ones pictured here go up for sale.
Estimate: $40,000–$60,000

Another romantic retelling of the HBC’s history, this 1942 painting depicts HBC trader Archibald McDonald’s very real journey down BC’s Fraser River canyon to his new post at Fort Langley roughly 120 years earlier. (He’s the well-dressed man in the middle, holding on to his top hat.) “I lived in Fort Langley, and we often visited that port on field trips,” says Heffel. “The collection as a whole touches so many corners of Canada.”
Sherriff Scott is a favourite among art buffs: for the last three decades, says Heffel, his paintings have graced the covers of Canadian art catalogues. “I think this will be many people’s favourite work in the offering,” says Heffel. “There’s going to be competitive bidding. It’s going to be a fun sale.”
Estimate: $7,000–$9,000
Anthony Milton is a freelance journalist based in Toronto specializing in long-form magazine writing. He previously worked as an assistant editor at Toronto Life, where he launched the Front Row newsletter. He regularly contributes all sorts of stories to the magazine, including deep dives on sports, business and housing as well as short-form commentary on our ever-changing city, from its obsession with cherry blossoms to its maddening NIMBYism. His work has also appeared in Maclean’s, Ricochet, TVO, the Trillium and more.