Heritage Winnipeg's 40th Annual Conservation Awards

 

I attended the 40th annual Heritage Winnipeg Preservation Awards on April 1, 2026 in the Crystal Ballroom of the Fort Garry Hotel. Many great people and buildings honoured. You can read about all of them in here at the Heritage Winnipeg website.

If there was a theme this year, it was "a labour of love", which came up in most of the acceptance speeches. None of these projects were particularly high profile, and in each case the owners could have found a cheaper option to do what they did. Instead, they all chose the long-term future of their buildings over short-term return on their repair dollars.

These are some of my additional notes about the awards. 

Residential Conservation Award: Roslyn Square (formerly Roslyn Court), 40 Osborne Street.

The Roslyn is owned by Globe Properties. Richard Morantz, CEO of Globe, said his father bought the building in 1969, and it has been the jewel in their portfolio ever since.

The award was primarily for the preservation of the building’s 500 windows. It was all custom work, of course, as nothing was standard sized, and took two years.

If I heard correctly during the owner’s acceptance speech, the project cost over $1.5m, or about a third of the building's assessed value. The owner said this illustrated that to renovate a building like this using proper methods, it a long-term investment.

Residential Conservation Award: Ches-Way Apartments at 240 Chestnut Street

I've followed this history of this building since 2020 and had a tour of it when it was completed last year. It took about three years from the time the owners got possession to it reopening. This was due to the amount of work that had to be done inside the brick potion of the block, which was a gut job due to it sitting vacant with a hole in the roof for a couple of years.

The amount of time and money that went into such a small building was enormous. What saved it was that it was over engineered, so there were no foundation issues to deal with, and it found a champion. New owners who felt that the neighbourhood deserved to have the Ches-Way around for another century.

Commercial Conservation Award: Saddlery Building, 284 William Avenue

I scratched my head about when I saw the program and wondered what building this was. When I Googled the address, I realised that I wrote about its history back in 2021. I'll have to update that post now that it has been renovated!

The building was literally on its last legs when CentreVenture stepped in to broker a deal to save it. Many surprises greeted the architects, engineers and construction workers after work got underway, but they worked together to save the structure and ready it for another century of use. 

Commercial Conservation Award: Fort Garry Hotel, 222 Broadway

What can you say about the Fort Garry Hotel? It is Winnipeg's gold standard when it comes to heritage conservation by a private owner. This award was primarily for the painstaking restoration of the old Palm Room, now known as the Oval Room Brasserie.

Ida Albo and Rick Bell have been the managing partners of the hotel for 33 years. Albo she said what restored the hotel's fortunes was that all the money made by the hotel were plowed back into the building. The Laberge family of Quebec did not expect a return on the hotel, they just wanted not to lose money with it, and Albo and Bell even lived at the hotel for their first thirteen to save money.

One of the recipients, the master plasterer responsible for much of the plaster restoration, says most of his career has been spent at the Fort Garry, starting with a years long project to restore the Crystal Casino space on the 6th and 7th floors back to its former glory.

A great business study could be made by comparing the city's two "grand old dame" hotels. The Marlborough, which sits vacant and may be turned into lower income housing, and the Hotel Fort Garry, which made itself into city's premiere hotel.

The Manitoba Museum will consor its exhibits if you complain

As reported by CTV Winnipeg the other day, the Manitoba Museum was to host another “Yuri’s Night” at the Planetarium on April 6th. It’s billed as “part of a global celebration of humanity’s past, present and future in space”. Sort of like a Jane’s Walk for space nuts. Yuri, of course, is Soviet cosmonaut Yuri Gagarin, who was the first person in space on April 12, 1961 - almost 65 years to the day of the event.

A small group headed by two Ukrainian women was insulted by the Manitoba Museum hosting a Yuri’s Night event, as Russia is currently at war with Ukraine, and complained. What did the museum do? Rather than try to explain the context and intent of the event, they cancelled it. This, despite its canned Facebook apology to people who complained stating: "Yuri's Night was never intended to be focused on Yuri Gagarin himself. While he became the first human to orbit the Earth in 1961, the focus is intended to be on this beginning of humankind's exploration of space, which has led humans to walk on the Moon, build space stations, and yearn to explore our solar system. The exploration of space is just one manifestation of the human spirit of exploration; our need to know, to learn, to discover."

Some might think, well Russia is at war, so best not to teach people about Russians in history, and feel that the Museum took some principled stance, but that is not the case. In the very same week as the space history exhibit was to be shown, the Museum held a viewing party for the Artemis II launch. This is a mission crewed by some members of the American military and funded by a regime that has threatened to make Canada the 51st state. It has also inflicted great economic hardship on our country with its tariff policies.
Furthermore, it is a big funder of the Israeli military machine that has been destroying Palestine since 2023, and started a war with Iran, which has spun out of control and caused instability in the entire region. The resulting spike in oil prices will further hurt Canadians.
The fact that one event was cancelled and the other went ahead shows that this wasn't some sort of principled response by the Museum, it just couldn't stick to its guns that an event about the history of space exploration had to include Gagarin. It caved into tenuous complaints.

There are two concerns I have with how this all played out. The first is how relatively quickly and easily the Museum will alter or edit its programming based on what are pretty tenuous complaints. That cat is now out of the bag, and it will make the Museum a magnet for other groups looking to right wrongs or get back at other groups by having people or events edited out of exhibits. The second is that the cancelling of Yuri Gagarin's name from its space history programming made the news. What programming or exhibits past, present and future have already been altered due to complaints from other groups, where the complainants did not run to the media? In the days of online misinformation, organisations like the Museum are the places that need to stand up for history and defend factual information that they are presenting. For me, I will now always wonder when reading something by, or seeing something at, the Manitoba Museum, whether or not events, people, or information has been edited out to appease community complaints.

Winnipeg photographer Israel Bennetto

© 2026, Christian Cassidy

I am working on a blog post about the 1880s house at 121 Kate Street. One of the residents I found there deserved a seperate blog post here!

Israel Bennetto was born in Hamilton, Ontario, in 1860 and came to Winnipeg in 1880. He soon opened Bennetto and Co. photography studio on Main Street and was one of just four or five five photography firms listed in the street directories of the early 1880s.

Bennetto married Anna Lauretta, and they had two young children, Litta and Israel Jr., when they moved to the house at 121 Kate Street in 1893. A third child, Marjory, was born in 1897.

Circa 1890s (EBay)

Bennetto's money was likely made in portrait photography. Surviving are images such as the above, a portrait of Mary Inkster, and images of  Winnipeg city council and its officials in 1888. 

When his studio moved to 436 Main Street around 1891, he also sold photography supplies and stock images of events and street scenes. This was a common practice for photographers as an additional income stream and a way to generate publicity for their services. For examples of his work, see here, here here, and here.

One of the most famous images attributed to Bennetto and Co. is this iconic portrait of Louis Riel that is still used today. It is unlikely that Bennetto took the photo himself, as the image is believed to be from the early 1870s and he was only born in 1860.

Perhaps, he purchased the rights to this image and others from an old-time photographer he came across? Another suggestion provided to me by a postcard collector is that he may have bought out an existing studio, and this was amongst its inventory.

Bennetto dabbled in property speculation, as many businessmen did back then. Likely finding it to be more lucrative than photography, he closed his studio in 1906 and spent most of his time in real estate.

It appears that in later years Bennetto subdivided parts of his Kate Street property and sold it off as residential lots. (See the 121 Kate blog post for more details.)

Assessment records show that all of the houses along the north side of Bannatyne between Kate and Juno streets, and a house next door to 120 Juno, were built in 1903. The large apartment at Bannatyne and Kate, famous for being on the cover of the Guess Who's So Long Bannatyne album cover, was built in 1910. 

The Bennettos moved from Kate Street in 1911. By this time, he had a new career, their two eldest children were in their twenties and Marjorie was 12.  They do not appear in Winnipeg street directories through the 19-teens. Perhaps Israel relocated further West to pursue his real estate ambitions.

Bennetto's new career did not keep him out of trouble. Plenty of money could be made in the land business  in the West during colonisation as new railway lines turned brush or farmland into town sites,  but there was also risk. Bennetto spent a lot of time in court being sued or suing others over land-relaed deals.

The Benettos were back in Winnipeg by 1920 and living at 100 Niagara Street. Marjorie got married later that year. 

Mrs. Bennetto died in June 12, 1929 at the Niagara Street home, aged 68. Israel died on June 4, 1946 at the Maple Leaf Apartments, 915 Corydon Ave, aged 86.

Glimpses of the old Winnipeg General Hospital

General Hospital on William, U of M Digital collections, H. Kalen fonds

I was at the HSC’s General Hospital section the other day. It's a place of fond memories for me as I spent many years there, starting in my mid-teens as a volunteer, then as an employee of the volunteer department's business wing.

Thanks to my job, I used to know the place like the back of my hand, so when I go back now it is strange to find buildings where exits or parking lots once were. Like layers of an onion, the hospital's oldest buildings go deeper into the core of the complex. 

The interior hallways of the main floor of the General Hospital's various buildings are now a single, generic “hospital hallway” décor and you can no longer tell when you are passing from one building to another. There use to be little hints like the age of office doors or a bit of molding at ceiling level.

I found two little spots on my walk around that show a glimpse into the General Hospital's past.

Through all of the renovations and additions, there is one little section of main floor hallway wall that has been left alone.

This is the elevator lobby for the Winnipeg General Hospital’s huge 1958 "north wing" addition along William Avenue (the photo at the top of this post.)

The Leo Mol bronze, described as a "contemporary representation of compassion", was donated by the White Cross Guild to commemorate the hospital's centennial in 1972 and unveiled in late December.

It contains a biblical phrase, “To heal the broken hearted – to set at liberty them that are bruised", followed by "Dedicated to all those who by their devoted labours and generosity have made it possible for this hospital to serve the community.”

It's unclear if the granite? marble? wall behind the artwork is original to the 1958 building or if it was added for the 1972 unveiling.

The following year, 1973, the General and its surrounding hospitals were amalgamated into the Health Sciences Centre.

Construction of East and West wings, 1913 (HSC Archives)

The other nice sight is a view of the ca. 1914 East Wing from Guildy's Cafe in the Thorlakson Building.

Thorlakson was constructed in the early 1980s facing Sherbrook Street and became the main entrance for the HSC complex. The space that is now Guildy’s Café used to be the HSC gift shop run by the Volunteer Department / White Cross Guild, (that's where its name comes from).

When the cafe was moved into the gift shop space, an inside seating area was created and part of the west wall was replaced with large windows. It provides a nice view from the cafe of the ca. 1914 East Wing  and a wee little courtyard with some benches. 

Winnipeg's Orpheum Theatre (1911 - 1946)

© 2026, Christian Cassidy

Winnipeg's Orpheum Theatre closed its doors 80 years ago this month. For just 18 of its 35 years it was the local home to the Orpheum vaudeville chain and brought town many performers who would go on to the be 20th century entertainment icons.

Here's a look back at the Orpheum's history.

Cross section looking at stage opening, (Archives of Manitoba) PAM

In late March 1910, a $450,000 building permit was issued to the Orpheum Theatre Co. to build a new venue on the east side of Fort Street between Portage and Graham avenues. (The land is now part of Winnipeg Square.) 

At the time, the California-based vaudeville company owned 18 U.S. theatres and had affiliate agreements with 14 more. It also had 25 affiliates in the U.K. and one in Paris and Berlin. Winnipeg was its first Canadian entry.

The primary architect for the new building was Kirchhoff and Rose of Milwaukee, Wisconsin. (It would later design a new Orpheum for Minneapolis, Minnesota in 1921). John D. Atchison was the local supervising architect. 

Work got underway in early April 1910 on the demolition of the existing building and stables on the site and excavation began by the end of the month. 

For reasons not explained in the newspapers, the construction schedule fell far behind over the summer. It was initially said that the theatre could be open by September 1, but by mid-August, workers were just erecting the steel superstructure.

One culprit in the delay was likely procuring its massive steel beam that measured 90 feet long by five feet wide. It was created at the Manitoba Bridge and Iron Works foundry on Logan Avenue at Arlington Street and was reported to be the "largest ever made or handled in Western Canada". It took three and a half hours to move it to the site on August 10.

The first manager of Winnipeg's Orpheum theatre was Clarence L. Dean.

Dean spent more than a decade in Europe as an agent for Barnum and Bailey's, then Buffalo Bill  Cody's Wild West Show. He returned to North America in 1910 to be the manager of the St. Paul, Minnesota, Orpheum theatre.

After ten months there, he and his family transferred to Winnipeg during the final stages of construction. He also oversaw the circuit's expansion to Regina, Calgary and Edmonton in affiliate theatres.

Dean left in November 1913, then E. J. Sullivan then took over the venue.

Sullivan had managed Chicago's Studebaker Theatre for several years before becoming a vaudeville talent agent. He stayed here until November 1924, then left to manage the Martin Beck Theatre in New York City.

The Orpheum's opening date was changed to mid-February, and then to March 6. It finally opened on Monday, March 13, 1911. It must still have been a rush job, as until the Saturday before its opening, patrons had to buy their tickets at Mason and Risch Piano Store on Main Street, and the building did not yet have its iconic electric sign. 

Patrons who walked through the door on opening night were greeted by a spacious lobby lined in white marble and a staircase on each side to go down to the men's smoking room or ladies' waiting room. The hall had five aisles and seated 1,875 on the floor, balcony and loges. Its carpet and velour-covered chairs were green, the curtain was lavender, and the walls were painted ivory with gold trim and accents.

The stage measured 40 feet wide by 34 feet deep and there was an orchestra pit to hold what was reported to be Winnipeg's largest in-house orchestra.

The opening week's show featured six acts headlined by Joseph Hart's The Bathing Girl Revue, a troupe of women singing, dancing and doing skits in Victorian-era swimwear.

Also on the bill were: Bert Coote and Company with a one-act comedic play called A Lamb in Wall Street; musical comedy from Cook and Lorenz; The Melnotte Twins with musician Clay Smith; European acrobats The Kremka Brothers; and Goleman's European Novelty, which featured tricks with dogs, cats and sometimes pigeons. 

Between acts, patrons were entertained by the orchestra, which sometimes accompanied a short Photoplane film. This was an early film projection technique that allowed films to be screened in full light to avoid eye fatigue and was installed in all Orpheum-owned theatres in 1911.

For the next couple of decades, a new show would arrive each week to perform a gruelling two performances daily from Monday to Saturday before moving on. There was a break of a few weeks in the summer months.

The Orpheum's fare was typical of vaudeville with a mix of dancers, singers, musicians, acrobats, comedians, and the odd animal show. Out of the thousands of performers who passed through the stage door, some stood out and went on to greater fame.

One example is “The Four Marx Brothers”, not in costume and under their real names of Herbert, Leonard, Arthur and Julius, who came three times. The first time was in late December 1917 with a comedy sketch called "Home Again". They returned in February 1920 with "'N Everything" and again in the first week of 1922 with "On the Balcony".

The next time Winnipegers saw them was on the silver screen in 1929.

The child dancing duo of Fred and Adele Astaire, she being Fred’s older sister, came in 1912 and 1917. Another dancer, Bill "Bojangles" Robinson, came in 1920, 1922, 1926, and 1927. 

One of its stronger weeks was in February 1923, when escape artist Henry Houdini and comedian Jack Benny shared the bill. Houdini had appeared at the Orpheum before in 1915. The 1923 visit included his great escape from atop the Free Press building.

Popular Ukrainian-American singer Sophie Tucker, who played Winnipeg numerous times, came under the Orpheum banner in 1912, 1916, 1917 and 1924.

Other entertainers of future note included: comedian W. C. Fields in 1912 and 1915; "The Oklahoma Cowboy" Will Rogers in 1913; singer and comedian Fanny Brice in 1916; and George Burns with Gracie Allen in 1927. 

Not all of the performers were traditional entertainers.

Helen Keller, with teacher/companion Anne Sullivan Macy, came in 1921 to address the crowd and answer questions. Newspaper reviews called her captivating and witty. She had been to Winnipeg before in 1914 under the auspices of the University Women's Club.

As seen in the ad above for the Helen Keller appearance, another name on the bill was violinist Marjorie Barrack. She was likely the only solo Winnipegger to make the bill on the Orpheum circuit.

Winnipeggers did do vaudeville, but it was more likely with Pantages, which wasn't Winnipeg-based but kicked off many of its vaudeville tours here and could add local performers to fill out or replace an act. Also, the Walker sometimes premiered touring productions here that would go on the road, such as the popular Winnipeg Kiddies shows.

The shows that arrived with the northern tour of the Orpheum circuit were usually well-established by the time they arrived here from St. Paul, Minnesota.

October 7, 1922, Winnipeg Tribune

Barrack began making a name for herself in 1910, around age fourteen, as one of the most promising young students of local music teacher Camille Couture and appeared regularly in recitals and small concerts around town. 

She spent the summer of 1914 in Dresden, Germany, as a student of Leopold von Auer. After she returned, she began performing as a soloist in Winnipeg and other cities.

By 1920, Barrack had married and went by Barrack-Beliveau, and signed on for her first tour with Orpheum as a violin soloist. A second 20-week tour began the following September, which is how she met Keller. The two remained in touch by letter. 

Two seasons were enough for Barrack, and she returned to Winnipeg to teach and play the odd concert here and in other cities, going as far as London, England.

Not all entertainers were veterans of vaudeville or looking for their big break. Some were already well-known stars and created a lot of buzz.

French singer and actress Sarah Bernhardt came to Winnipeg twice on the Orpheum circuit along with her own cast and crew. 

The first visit was from January 6 to 12, 1913. In an unusual move, there was an extended break between Berrnhardt's show and the rest of the bill so that patrons could opt to pay to come see just her.

To ensure repeat visits, Berhnhardt and her company varied their performances. On Monday, it was Lucrezia Borgia act III, Tuesday was La Tosca act III, Wednesday and Thursday was One Christmas Night, and Friday and Saturday was Camille act V.

On her second visit in 1918, she and her players performed a war-inspired one-act play called "From the Theatre to the Field of Honour" from Monday to Wednesday, and "Camille" from Thursday to Saturday. As with her previous visit, there was special pricing to see just her show.

December 14, 1927, Winnipeg Tribune

Vaudeville struggled to fill seats though the 1920s due to the popularity of talking pictures which had become the entertainment of choice amongst the masses. In order to survive, Orpheum's parent company was part of several huge corporate mergers.

The first was in December 1927, when it merged with the Keith-Albee Company to create Keith-Albee-Orpheum, which boasted 500 theatres across North America, both movie houses and live venues. The following year, Radio Corporation of America, (RCA) joined the fold and the parent company became known as Radio-Keith-Orpheum, or RKO.

A division of RKO called RKO Pictures would soon become one of the big five movie studios during Hollywood's golden era.

In May 1929, RKO and Famous Players Canada created RKO Canada Ltd., which saw Famous Players take over the operation of RKO’s Canadian theatres (this was likely just Winnipeg and Vancouver in the West.)

Both the Orpheum and Famous Players' Capitol theatres closed in the summer of 1929 for repairs and rebranding.

The rechristened RKO-Capitol, built as a movie theatre, received extensive renovations and reopened on September 23rd as the home to both first-run movies and Orpheum's live vaudeville shows.

The Orpheum, now called RKO-Winnipeg, reopened on October 2nd as a movie house with Clara Bow's "Dangerous Curves" and was also a theatre for hire for speeches, sermons, ceremonies, recitals and other events.

As the 1930s wore on, the RKO-Winnipeg's role as a first-run movie venue waned. It soon introduced British films to its lineup, then began offering special nights with two-for-one admissions. The stage for rent devolved into weeks of boxing and wrestling matches in early 1933.

It appears the theatre may have closed for all but rental events in late 1934 and 1935. It reopened in January 1936 under the name Winnipeg-Orpheum to show films and host special events. 

In the 1940s, the Orpheum was leased out as a military recruitment office in its lobby and to host shows for troops and their families in the hall.

On January 24, 1946, a group of local businessmen announced that they had purchased the theatre from Famous Players for around $30,000 on the condition that it not reopen as a theatre. Famous Players oversaw the removal of seats, projectors, lighting and anything else that made it a theatre.

The last show to take place at the Orpheum was the 235th and final performance of the City Hydro concert troupe on February 10, 1946. This revue featured a mix of singers, musicians, and dancers that began its shows to entertain military personnel and their families at Camp Shilo in May 1939.

The building was demolished later that year and the land became a surface parking lot. It was incorporated into the Winnipeg Square development in the 1970s.

Kenneth Leishman - The Flying Bandit

© 2008, 2011, 2026, Christian Cassidy. Please respect my research.

I first wrote this post back in 2008, (before West End Dumpling even existed!) and have updated it a couple of times over the years to fix broken links and other formatting issues. It is likely my most popular post, as it still falls inside my top 20 most-read blog posts each year, and I am often asked to contribute to news stories about Leishman. I thought it was finally time to bring it over to West End Dumplings on the 60th anniversary of Leishman's great heist!

I will leave the old post up as it has generated many comments over the years, some from people who knew Ken!

Leishman in 1966, U of M Archives, Wpg Tribune Collection

William Kenneth Leishman, also known as the 'Flying Bandit' or 'Gentleman Bandit', has been referred to as “one of the most beloved of Canadian criminals.” This is thanks to his family man persona and polite demeanour. 

In the 1950s and early 1960s, he committed numerous crimes, including warehouse thefts, bank robberies, and prison breaks. His piéce de resistance was the March 1, 1966 heist of nearly $400,000 worth of gold bullion from the Winnipeg International Airport, which was the largest gold theft in Canadian history until a 2023 heist at Toronto's Pearson International Airport.

Instead of being labelled a public enemy, the North Kildonan kitchenware salesman and father of seven charmed Canadians and gained a sort of 'criminal folk hero' status, which is pretty rare in this country.

Here is a look back at the life of Ken Leishman.

1931 Census of Canada (source: Library and Archives Canada)

William Kenneth Leishman was born on a farm in Holland, Manitoba, on July 20, 1931, to Norman Allan Leishman of Treherne and Irene Beatrice Agarand of Holland.

The couple married in Winnipeg on September 25, 1928 and the 1931 census entry above shows them, just weeks before Ken was born, living at the Agarand farm with daughter Elizabeth. They would go on to have a third child named Robert.

Norman was good with his hands and worked fixing farm machinery.

Holland, MB ca. 1910 (Source: Peel's Prairie Provinces)

Holland was a pretty typical Manitoba farming community. At the time, had at least three or four grain elevators that were serviced by the two railway lines that passed through town. It also had a bustling Main Street thanks to the 400 or so area residents.

This prosperity changed as the Depression wore on. The effects of drought and bottomed-out commodity prices rippled from farmers to farm workers to townspeople.

Norman and Irene separated in 1938, not long before he went off to serve in the Second World War, and they divorced in 1943. This left Mrs. Leishman in the terrible predicament of being a single mother of three in rural Manitoba at the tail end of the Depression.

Irene managed to find a live-in domestic job with an area widower. The man and Ken, then seven years old, did not get along. According to Irene, it led to the physical abuse of the boy. She was then given an ultimatum: give up her job, which was also her home, or give up Ken.

She made what must have been a wrenching decision to send Ken into foster care and he bounced from foster home to foster home, then landed in a residential orphanage after Children's Aid seized him from an abusive household.

After the Leishman divorce was granted in 1943, Irene married William "Bill" Brooking of Treherne, Manitoba. He, too, had issues with Ken and at age 14, he was sent to live and work back on his grandparents' farm.

The farm brought a stability to Ken's life, though he was prone to accidents. One time he was kicked in the head by a horse, something Irene claimed in the 1960s may have accounted for some his bad behavior (source: Winnipeg Free Press Nov 2, 1966).

565 Lipton Street in 2012 (Source: Google Street View)

At age 16, Ken tried to reconcile with his father and came to live with him in Winnipeg.

Norman had served with the A15 Infantry Training Centre at Shilo, Manitoba, where he reached the rank of lance-corporal. There, he met Norah Nancy Michels, who had enlisted with the Canadian Women's Army Corps and was also assigned to Shilo. The two married in 1944.

After the war, the couple settled in Winnipeg, where Norman worked for Western Elevator and Motor Company and Norah for Eaton's. They initially lived in a small apartment on Garry Street before moving to a house on Lipton Street in the West End. Ken stayed with the couple on Lipton Street.

In the summer (likely of 1947) Ken went to cottage country to work at a resort in Kenora. He ended up breaking his ankle not long into the job and had to return to Winnipeg.

Wedding photo (Source: Leishman family, Calgary Sun archives)

At age 17, Ken returned to one of the towns he stayed at when he was a child, likely Holland or Treherne, to attend a funeral. There, he met Elva Shields, who would later say that it was "love at first sight". The two stayed in touch and were married on February 25, 1950, in Winnipeg.

Elva got a sign of things to come when Ken spent a few months of their newlywed year in jail.

Ken worked part-time with his father at the elevator repair company, which gave him access to a variety of buildings. He cased the interior for products he wanted, then came back after hours to break in and, posing as an employee of that company, called a transport company to deliver the goods to the couple's suite on Gertrude Street.

In February 1950, weeks before his wedding, his thefts included: a radio from a downtown building; a fridge and range from the Westinghouse building; a chesterfield suite, dinette suite and chairs from a Genser's warehouse on Market Street; a bed and kitchen suite from the Genser's warehouse on Ross Avenue. The total value of the goods was just under $1,000.

The arrest came in early March while at a return visit to Genser's Ross Avenue warehouse. The transport company dispatcher was suspicious of getting a call so late at night and tipped off police.

Ken pleaded guilty and was sentenced to nine months in jail. He apparently got out in three due to good behavior.

Leishman in Rosenort area, undated (source: RM of Morris history book)

After his release, Ken pursued another interest of his: flying.

It is unclear where this love came from. He could have been exposed to small planes in his youth through crop-dusters servicing Manitoba farmland. It could also have been during the Second World War when southwest Manitoba was dotted with hangars, airfields and control towers for the British Commonwealth Air Training Plan.

Ken took flying lessons, bought a plane, and began a series of fly-in machinery repair and sales jobs to rural communities. (In October 1953, he received a two-year suspended sentence for flying without a pilot's license - it is unclear whether he obtained one after that, or if he just kept flying.)

Winnipeg street directories show that through the 1950s, the Leishman family lived at various addresses, usually a new one every year. They included: 752 Seven Oaks Avenue in West Kildonan (1951–1952), 113 Roberta Avenue in East Kildonan (1953), 661 Pembina Highway (1954), 525 Castle Avenue in Elmwood (1955), 1904 Dawson Road near Navin (1956), and 874 Lindsay Street in River Heights (1957). 

When Ken first got out of jail, he was a switchman with the CNR, then in 1951 he rejoined his father, who had become general manager of Mid-West Elevator. He worked at both the elevator company and seasonally for several companies and flew into rural and remote communities to do machinery repairs or sell things like cutlery, pots and pans, and household utensils. The companies were Machine Industries, International Steel, Reno Wear Distributors, and Ken-Mae Enterprises.

In March 1957, Ken was a member of the newly founded Manitoba Volunteer Air Patrol, a civil defense organization, and was in charge of organizing a national meeting in Winnipeg on the topic of having a nationwide VAP. This involved meeting high-level officials in Ottawa.

December 18, 1957, Canadian Press

Outward appearances were that Ken was doing well with a big family, a house in the suburbs, a plane, a Cadillac and an expensive wardrobe. The truth was that he was living well beyond his means and in 1957, he started to supplement his income by robbing banks.

Ken decided that he would go to Toronto to commit the robberies. He later told police that while Manitobans had money, it was usually tied up in land, equipment and other investments. Toronto, he felt, was where cash flowed more freely.

In December 1957, he boarded a commercial flight to Toronto, rented a nice car and checked into a luxury downtown hotel. The following day, after some clothes shopping, he committed what the Canadian Press reported was “one of the most daring robberies on record.”

Posing as "Mr. Gair", a Buffalo businessman, he entered the Toronto-Dominion Bank at Yonge Street and Albert Avenue and asked to meet with the manager. Inside the office, Ken produced a gun, forced the manager to write a cashier's cheque for $10,000, and stayed with him while he cashed it at one of the tellers. He had the manager escort him to his car, then wished him and his family a very Merry Christmas before speeding off.

Witnesses described Ken as well-dressed, polite and dignified, which led to the "Gentleman Bandit" nickname. 

Ken returned the car and took his return flight to Winnipeg that evening. His family thought he had been on one of his fly-in sales jobs. 

Interior of Second bank robbed (Ottawa Citizen)

In March 1958, Ken was back in Toronto to rob the Canadian Imperial Bank of Commerce at the busy intersection of Bloor and Yonge streets. This time, when he showed the gun to the manager, who reacted angrily, and a scuffle ensued. A staff member noticed the racket and sounded the alarm.

While fleeing the building, Ken tripped over someone on the sidewalk. Another pedestrian, a minister, kicked the gun out of his hand. Bank staff then held him until police arrived.

March 19, 1958, Winnipeg Free Press

Ken's arrest and the exploits of "The Flying Bandit" were front page news across the country. The fact that this daring robber wasn't some gangster, but a well-dressed kitchenware salesman from River Heights, gave the story extra life.

As for Elva, who was expecting the couple's sixth child at the time, she claimed she knew nothing of the robberies and only learned about his arrest when two of her children came home from school in tears after having been teased about it by fellow students. She said, "I never pry into his affairs. He is a perfect husband and father and just a wonderful guy."

Ken pleaded guilty to the two robberies and he was given a 12-year sentence at Stony Mountain Penitentiary. He was paroled in just 3.5 years after being described by Stony’s warden as a ‘model prisoner’.

To put food on the table while Ken served his sentence, Elva operated Elva's Gift Shop at 2635 Portage Avenue in St. James. 

After jail, Ken went back to fly-in sales with a company called World Wide Distributors, selling kitchenware and silverware. After a couple of years with the company, he was made a supervisor and the family purchased a new home at 482 Mark Pearce Avenue in North Kildonan.

Despite appearing to settle down, Ken was actually plotting his biggest caper yet.

March 12, 1966, Winnipeg Free Press

The next time Winnipeggers saw Ken Leishman on the front page of the papers was in March 1966, after he was arrested at Vancouver's airport for a parole violation. He was returned to the city under RCMP escort on March 11 in what the Winnipeg Free Press called "one of the hushiest hush-hush police operations on record in Winnipeg."

Proceedings soon got underway to return Ken to Stony Mountain to fulfill the remainder of his 12-year bank robbery sentence, while Winnipeg police worked behind the scenes to charge him for something bigger: the Winnipeg International Airport gold heist of March 1, 1966.

Winnipeg Int'l Airport, Undedt (Source H. Kalen fonds, U of M Archives)

Through his connections in the local aviation community, Ken knew that TransAir, an airline that connected Northwest Ontario and Winnipeg, regularly flew gold bullion from Red Lake, Ontario, to the Winnipeg International Airport where it was transferred to an Air Canada Cargo flight bound for Ottawa and the Royal Canadian Mint. (This was a decade before the mint's coin striking facility opened in Winnipeg.)

Ken's plan was both daring and simple: intercept the gold on the tarmac and drive off into the sunset.

Unlike his previous thefts, Ken needed accomplices for this one. They included three bar buddies and a Winnipeg lawyer named Harry Backlin. While studying law, Backlin visited prisoners at Stony Mountain. He and Ken hit it off and even went into business together after Ken was released in a cleaning supplies wholesale company.

Items required for the heist were assembled. Blank waybills were taken from an Air Canada Cargo counter. Two pairs of white coveralls, similar to what Air Canada Cargo ground crews wore, were purchased and crude Air Canada logos were stencilled on using red markers. The parking lot where the airline kept its cargo vans after hours was also scouted.

March 2, 1966, Winnipeg Tribune

An accomplice in Red Lake tipped Ken off that a TransAir bullion flight would arrive in Winnipeg on the night of March 1, 1966, and the plan was put into motion.

Before the flight touched down, two of the bar buddies hotwired an Air Canada Cargo van and drove onto the tarmac through a back gate. They met the plane, showed the TransAir crew a fake waybill, and the gold was loaded into the van.

The two drove away with nearly $400,000 in gold bullion, each of the twelve bars in its own wooden box. It was Canada's largest-ever gold heist.  (Edit: It may still be Canada's largest. The 2023 Pearson International Airport heist made off with $23 million in gold and some call that the largest. To compare apples to apples, you would need to take the number of ounces stolen in 1966 and put it through a gold inflation calculator to find its 2023 value.)

After the heist, the two men drove about a kilometre away where they had stashed a getaway car. The gold, which weighed about 600 pounds, was transferred in its boxes to the new vehicle and driven to the small warehouse that Ken and Backlin ran their cleaning supply business out of. 

The plan was for Ken to then drive the gold to the farm of a relative of Backlin's a couple of hours away from the city, but Mother Nature interfered.

March 4, 1966, Winnipeg Tribune

A Colorado Low was sweeping into the province with strong winds and heavy snowfall. In the next 24 hours, it would become one of Winnipeg's worst blizzards.

Ken knew that minutes after the heist, when the real Air Canada Cargo crew showed up for the gold, the alarm would be raised and that could mean Winnipeg Police or RCMP roadblocks. With the car heavily weighed down and the weather worsening, he realised it would be a much longer and riskier drive than he had anticipated.

The "plan B" was to take the gold to Backlin's home at 119 Balfour Avenue in Winnipeg's Riverview neighbourhood. Backlin was out of town and unaware of the plan, but his mother was housesitting. She opened the door for Ken, who told her he had the boxes of moose meat that Backlin had ordered. He was shown the chest freezer in the basement and stashed the gold there.

When Backlin returned home, he was unimpressed with Ken's decision and took the gold and buried it in the snow in his back yard to avoid raising his wife's suspicion.

March 12, 1966, Winnipeg Free Press

The two men had to act fast as the snow wasn't going to stay around for long in early March. They decided to forego stashing it somewhere else for the longer term and instead try to sell it on the black market in Hong Kong. 

Unfortunately, both men had passport issues. Backlin had recently anglicized his name, and his old passport was at the passport office while he awaited a new one. Ken was still on parole, and if someone checked the name on his passport they would find that he could not leave Manitoba, much less the country.

Desperate to get rid of the gold in a hurry, they decided to take a chance. Backlin bought a ticket to Hong Kong, and Ken travelled using his own passport.

Ken reached the Vancouver airport with part of one of the gold bars in his luggage to show potential buyers the quality of his product. Some sources say he noticed a strong police presence, others say that he was paged over the PA system to report to customer service. Whichever it was, Ken got spooked and ditched the gold outside the terminal. To this day, nobody knows what happened to it.

The RCMP closed in, and to Ken's surprise he was arrested for parole violation with no mention of the gold.

March 11, 1966, Winnipeg Tribune

Ken was returned to Headingley Jail for the parole violation and was awaiting his hearing that would return him to Stony Mountain to serve out the rest of his "flying bandit" sentence. Behind the scenes, Winnipeg police were working hard to pin the gold heist on him.

The abandoned Air Canada van was found with a fingerprint of one of the accomplices inside. Police eventually tracked down the two drivers, and through interviews and the use of a cellmate informant, the story of the heist was laid bare.

On March 20, 1966, Ken and four accomplices, including Backlin, were charged with conspiracy and robbery. Of the twelve bars of bulion, ten were dug up from the snow drift behind Backlin's house and another was found at his Portage Avenue office. Part of the twelfth was ditched by Ken at the Vancouver International Airport and it is unclear what happened to the rest of it.

The arrest of Backlin was quite newsworthy as he was a fairly well-known lawyer by that time. The man who defended him in court was a young Roland Penner, who would go on to be a long-time Manitoba MLA and attorney general.

September 6, 1966, WInnipeg Free Press

While at Headingley Jail, Ken masterminded the escape of ten prisoners, himself included.

On the evening of September 1, 1966, one member of the group overpowered a guard and stole his keys. Others entered the guard office and stole weapons. Within fifteen minutes, they were outside the gates.

Ken, along with three other prisoners (a murderer, a rapist, and someone awaiting transfer to Selkirk Mental Hospital) stole a Chevrolet from the prison parking lot and took off. This started what is believed to be Manitoba's largest manhunt.

Every municipal police force was placed on high alert and told to set up roadblocks at the perimeter of their communities. Manitoba RCMP called in every officer on the force and manned their own roadblocks on highways throughout southern Manitoba. Bordering provinces and states were also alerted.

Return to Winnipeg. (Source:Tribune Photograph collection, U of M Archives)

Ken and company made it to Steinbach, where he stole a small plane and the four headed across the border. They landed in a farmer's field outside Gary, Indiana, where Ken sweet-talked the farmer into giving them a ride into town.

The men rented a hotel room and went down to the bar to celebrate. The bartender recognized them from a news report. Their use of Canadian bills to pay for their room and drinks helped confirm his suspicion.

When police arrived, Ken and one of the escapees gave themselves up. The other two led police on a foot chase and were captured. The four arrived back in Winnipeg on September 9, 1966.

West Kildonan officers. (Source:Tribune Photograph collection, U of M Archives)

Ken found himself at the Vaughan Street Jail awaiting his hearing for an even longer list of charges. By this time, the jail was used mainly as a remand centre, as Winnipeg's Public Safety Building had just opened, so Ken was held in an empty wing and had access to the corridor outside of his cell.

On October 30, 1966, Ken picked the lock on the old steel door at the end of the hall, overpowered three guards, and escaped through a back door to freedom.

Four hours later, Ken called his lawyer from a phone box at Main Street and Jefferson Avenue. The lawyer either convinced him to give himself up, or he turned him in, as minutes later two officers from the West Kildonan Police Department showed up and Ken surrendered peacefully.

The next day, jail administrators had experts examine the massive, ancient steel door to see how Ken managed to turn the locking bolts. They were baffled and called the escape 'miraculous'. (After his conviction, Ken was asked to demonstrate his MacGyver-esque moves for them. He used just a strip of cloth and a piece of wire.)

On November 1, 1966, Leishman pleaded guilty to all nine charges against him. He received a sentence of nearly 15 years, seven for the gold heist and escapes, plus the remaining eight years left on his Toronto bank robbery sentence.

November 2, 1966, Winnipeg Free Press

Ken spent his years in prison reading and writing poetry, but he had one more escape up his sleeve.

In June 1974, he applied for parole and was denied. He then requested an official review of the length of his sentence, which was a complicated web of various sentences dating back to Toronto, some to be served concurrently and some not. The parole board panel did the review and found that his sentence HAD been improperly pieced together at his last sentencing. It ruled that because of the error, Ken should be released immediately! 

The ruling sparked a review of hundreds of similar sentences across the country.

Elva and Ken with son, Trent (left), February 5, 1980, Winnipeg Tribune

After his surprise release in 1974, it appears that Ken was ready to settle down and make up for lost time with his family.

By 1977, the Leishmans had moved to Red Lake, Ontario, where Ken took a job as a bush pilot and opened a tourist gift shop that he ran with Elva. The couple, who became devout Mormons, were well-liked by community members. Ken served as the chair of the local Chamber of Commerce for a time and lost a 1978 bid to become reeve by just 75 votes.

90 Minutes Live, CBC, February 21, 1977

There was also time to enjoy wider-scale notoriety of being the 'Flying Bandit', the mastermind behind Canada's largest gold heist, and an adept escape artist. There were newspaper and magazine interviews, and likely his biggest audience was on the February 21, 1977 edition of the short-lived Peter Gzowski TV talk show, 90 Minutes Live. (Sadly, that clip has disappeared from the internet.)

Ken had become a folk hero. A charming but unassuming family man who tried his best to "stick it to the man" by robbing banks, stealing from the mint, and breaking out of jail. All done with a healthy dose of Canadian courtesy and manners.

Ken was working on a manuscript about his life in 1979, and according to Tribune entertainment columnist Gene Telpner, actor Darren McGavin bought the rights to the story. Ken said that he and his wife went to California to meet McGavin and potential filming locations were being scouted north of the border. It is unclear what happened as the project never materialised. (And, surprisingly, nobody else from Hollywood has ever picked up on Leishman's story in the decades since!)

December 18, 1979, WInnipeg Tribune

Ken continued to fly and performed midi-vac flights for the area.

On December 14, 1979, he was performing such a flight with a twin-engine Piper Aztec from Sandy Lake First Nation to Thunder Bay when his plane disappeared. Several searches of the dense bush were done, but it was not until spring that a Canadian Forces search flight found the wreckage.

The bodies of the patient and medical assistant were positively identified, but all they could find of Leishman was his wallet and some scraps of clothing.

Given his colourful past, there was speculation that the Flying Bandit may have escaped again. At the inquest into the deaths, however, experts concluded that he likely could not have survived the crash, much lass walk for hours through the dense bush. It concluded that his body was likely taken away and eaten by wolves.

On December 16, 1980, Ken Leishman was declared legally dead at the age of 48. He left behind his wife of 30 years, seven children, and quite a legend.

May 8, 1980, Winnipeg Tribune

Ken's obituary appeared in Winnipeg newspapers on May 8, 1980. The story of his life starts abruptly in 1974, as if he began a new life after prison. It concludes with a poem that he wrote (see above).

Elva Leishman moved to Gridley, California, in 1980, where her daughter and family lived, and remarried. She died in 2021 at the age of 93.