Windsor Hotel's history began bright, ended in flames and blight

A piece of Winnipeg's entertainment history is now rubble, the ghosts of its legendary performers and guests released in columns of smoke and flames on Wednesday.

History of Winnipeg hotel destroyed Wednesday includes connection to Charlie Chaplin's last days in vaudeville

A black and white photo of the exterior of a brick building with the name Windsor Hotel.
The Windsor Hotel as seen in the 1980s, during its heyday as the home of the blues. (Heritage Winnipeg)

A piece of Winnipeg's entertainment history is now rubble, the ghosts of its legendary performers and guests released in columns of smoke and flames.

The 120-year-old Windsor Hotel burned to the ground Wednesday in a bitter, forlorn ending after troubled years that put the hotel prominently on the police radar, then saw it closed down under a provincial health order.

"I'm just really, really sad that it's gone," said local historian and blogger Christian Cassidy. "It's obviously a landmark … and it is a very familiar sight on the street there. It's sad to lose it."

While it wasn't a hotel featured on postcards or lauded like the grand railroad hotels that drew the higher class of society, the Windsor — or La Claire Hotel, as it was previously called — served an important role in the city, Cassidy said.

"It was never a spectacular hotel. It was one of these middle-class-slash-working-class hotels all of its life," he said.

"That's an important part of the history of a city because those are the people who built the city — not the people who financed things or the people who made political decisions, but the people who rode the rails and drove the streetcars and taught the schoolchildren and sold the the farm machinery being produced in the Exchange District."

Smoke billowing out of the vacant Windsor Hotel Wednesday morning in winnipeg.
Smoke billows out of the vacant Windsor Hotel in downtown Winnipeg Wednesday morning. (Warren Kay/CBC)

Before its tailspin in the last decade, the Windsor had a celebrated reputation.

It began in 1903 as Le Claire Hall Apartments, a brick-and-stone, three-storey boarding house described as a "magnificent new facility … designed by the owner to satisfy the most finicky tastes of our clients," according to the Manitoba Historical Society.

"Living in a boarding house was a perfectly acceptable way of living, especially for single men," Cassidy said.

"There were probably a lot of clerks and railway employees and seasonal workers, travelling salesmen. A lot of people who would first come to town would stay at a boarding house the first few months while they got themselves set up."

It was redesigned as a hotel in 1910 and renamed as La Claire Hotel. At that time, both Winnipeg's population and economy were booming, and the city was an important stop on the touring vaudeville circuit.

The Chaplin connection

Located on Garry Street, just off St. Mary Avenue in the city's downtown, the hotel was a couple of blocks from Union Station, where tourists and performers arrived by train. Among them was Charlie Chaplin and a vaudeville show of British actors he toured with across North America.

"This was in the days before stardom. These were a bunch of working-class performers that were travelling the country," Cassidy said.

But one Winnipeg stop, in 1913, came at a decisive point in Chaplin's life.

A three-storey brick building can be seen in this photo. A sign on the front says "Windsor Hotel," and below that another sign says "Cold Beer."
The cardboard cutout of Chaplin peers out from the balcony of the Windsor Hotel in a February 2023 photo. (Cameron MacLean/CBC)

He was performing at the Empress Theatre (where the Fairmont Winnipeg now stands) when a fellow vaudevillian was also in town and happened to pass by.

Julius Henry "Groucho" Marx wandered from Union Station while waiting for a train, and heard roars of laughter at the Empress. He stepped in briefly to see Chaplin for the first time. He told his brothers about the great comedian, whom they later met up with in Vancouver.

They would meet again several times, eventually touring together and becoming lifelong friends, which Marx wrote about in his 1959 autobiography Groucho and Me.

A letter with the silhouette of a man in a derby hat
Charlie Chaplin's note, on La Claire letterhead, to his brother, telling him he'd been offered a movie contract. The shadow watermark was added by the Charlie Chaplin Archives. (Charlie Chaplin Archives)

During the same stopover, Chaplin wrote to his brother, telling him he'd received a proposal that changed the direction of his career.

"He got an offer from Mack Sennett, who was this silent film producer. [He] was inviting Charlie to come to Hollywood to make movies. At this point he'd just been a stage actor," said Winnipeg music historian John Einarson.

It's not totally clear when he'd received the offer from Sennett, but "on La Claire stationery, Charlie wrote to his brother in New York to say that after the gig in Winnipeg, he wouldn't be coming back to New York. He was going to take the train to Hollywood, Los Angeles, and make movies," said Einarson.

An exterior view of a brick building being demolished
Excavators were called in soon after the fire was extinguished and all that was left were some partial walls on Wednesday evening. (Christian Cassidy/Facebook)

The letter is part of the Charlie Chaplin Archive, but a copy used to hang in the Windsor lounge.

"So his career kind of pivoted while he was here in Winnipeg," Einarson said.

The hotel played that connection up in later years, adding an external mural featuring Chaplin. A life-sized cardboard cutout also stood on the third-storey wrought-iron balcony above the front entrance.

Blues bar

A one-storey annex was added on the north side of the hotel in 1928 as a licensed gentlemen's club and the hotel was sold to the Windsor Hotel Company, which changed to the name.

A 1948 industry magazine described the Windsor Hotel as among Manitoba's "best accommodations," with 53 rooms costing "$1.75 and up" per day, according to a 2005 annual report by the City of Winnipeg's Historical Buildings Committee.

The hotel changed ownership a handful of times, and its reputation began to slide. It was revived in the 1970s when the annex became a key music venue.

"We had for a long time a very strong blues fraternity, and the home of the blues in Winnipeg was the Windsor Hotel, beginning in the '70s and through the '80s and '90s," Einarson said.

"A lot of the greats played there. People like Colin James and Jeff Healey, Matt Minglewood, Dutch Mason, the Downchild Blues Band, Jack Semple all took the stage at one time or another. Big Dave McLean hosted weekly jam sessions there for 28 years before moving over to [the Main Street venue] Times Change(d)."

The Manitoba Blues Society held an annual event there. And Randy Bachman, a founding member of the bands The Guess Who and Bachman–Turner Overdrive, played there when he launched a jazz album in the early 2000s.

"It was kind of funky, cool. It was like an oasis for blues fans," Einarson said.

As criminal activity increased, though, the crowds and the number of musicians wanting to play at the hotel decreased.

A cyclist rides by a pile of rubble in a city downtown.
The rubble remaining the day after a Wednesday fire that gutted the 120-year-old Windsor Hotel in downtown Winnipeg. (Prabhjot Singh Lotey/CBC)

It was sold earlier this year, then shut down under a provincial health order, sending about 20 low-income residents into the street.

Finally, on Wednesday morning, fire crews were called as columns of smoke billowed from windows of the hotel. By the supper hour, the hotel was just a memory. 

All that's now left of the hotel is a pile of rubble. 

The cause of the fire has not been determined.


Darren Bernhardt spent the first dozen years of his journalism career in newspapers, at the Regina Leader-Post then the Saskatoon StarPhoenix. He has been with CBC Manitoba since 2009 and specializes in offbeat and local history stories. He is the author of award-nominated and bestselling The Lesser Known: A History of Oddities from the Heart of the Continent.