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Saturday, 15 November 2025

Farewell, Olafson House


Sadly, Gisli Olafson House at 539 William Avenue was torn down on November 13, 2025 after its fourth fire in three months.

I spent a lot of time at the HSC when I was in my teens and passed this place weekly on the bus. It was one of my favourite houses in the city and young, innocent me thought that one day I might buy it, renovate it (with a book nook in the turret) and live there.

Here's a look back at its history and some of the people who called it home over the past 130 years.

Tuesday, 4 November 2025

The final flight of sergeants John McPherson and Joffre McDonald of Winnipeg

 © 2025, Christian Cassidy

When I was doing research for a tree walk of Elmwood Cemetery earlier this year, I came across this non-military headstone marker for an RCAF pilot who died during the Second World War.

I thought I would find out more about his story and why there is no military headstone next to it.

It turns out this is a memorial to, not the actual grave of, John Roderick McPherson, and it tells the story of four men who lost their lives.

Operation Picture Me at Canadian Virtual War Memorial

John Roderick McPherson was one of six children of Peter and Minnie McPherson. His father worked for the legal department of the CPR, and the McPherson family moved into their long-time family home at 1169 Grosvenor Avenue around 1915.

McPherson attended Kelvin High School and the University of Manitoba. Upon graduation, he got a job as a grain clerk and still lived at home. The company he worked for was the Inter-Ocean Grain Company in the Grain Exchange building. It was a small player with around ten elevators in the province at the time.

March 14, 1942, Winnipeg Free Press

In March 1941, at the age of 24, McPherson enlisted in the Royal Canadian Air Force. After training at various prairie posts, he received his wings in December 1941 and was assigned to the 113 Bomber Reconnaissance Squadron, Yarmouth, Nova Scotia.

Before leaving, he married Maeve Renahan at a ceremony at his brother-in-law’s house at 1125 Wellington Crescent. Maeve accompanied her husband to Yarmouth.

Sadly, McPherson's marriage and his military career would be short.

Lockheed Hudson, (Source: Australian Air Force)

On Monday, June 1, 1942, four men were assigned to a routine anti-submarine patrol around the Bay of Fundy. They were: Pilot Officer Trask O'Neil Johnson (27) of Charlottetown PEI; Sergeant John Roderick McPherson (25) of Winnipeg, who was second pilot; Sergeant Joffre Kitchener McDonald (26) of Elkhorn MB; and Charles Leonard Scholey of Ryerson, SK.

Their Lockheed Hudson took the the air at 11:53 a.m. and was never heard from again. A search by ships and planes in the region turned up nothing.

December 12, 1942, Winnipeg Tribune

An RCAF inquiry was held on June 3 and seven witnesses were called. The weather and visibility were said to have been good that day, and the crew who had just returned from a 5.5-hour flight with the same plane said that it was in good working condition.

The jury's verdict on the reason for the accident was "Unknown. None of the evidence throws any light on the loss of the aircraft".

The four airmen remained "Missing - Presumed Dead" until December 9, 1942, when the families were informed that they had been declared "Presumed Dead".

It is unclear what happened to Maeve McPherson. She was originally from Toronto and her parents still resided there. It is possible that she never returned to Winnipeg.

Operation Picture Me at Canadian Virtual War Memorial

There was a second man on the flight with a local connection.

Sergeant Joffre Kitchener McDonald was born at Fleming, Saskatchewan but moved as a young man to Elkhorn, Manitoba. That is where he lived when he enlisted in Edmonton.

McDonald's mother and some of his siblings lived in Winnipeg. He listed is mother, Mrs. Matilda McDonald of suite 5 of Howell Court, as his Next of Kin.

Like McPherson, the family was informed on December 9, 1942 that he was Presumed Dead.

Veterans Affairs Canada

As their bodies were never found, the men are officially commemorated by the Ottawa Memorial (Commonwealth Air Forces) in Ottawa. The inscription reads in part: "In honoured memory of the men and women of the air forces of the British Commonwealth and Empire who gave their lives in Canada in the United States of America and in the neighbouring lands and seas and who have no known grave."

As noted above, the McPherson family decided to erect a memorial marker at Elmwood Cemetery in Winnipeg. McDonald is also listed on the Elkhorn Cenotaph in his hometown. 

For more:
Lockheed Hudson accident detail Canadian Warplane Heritage Museum (scroll to serial no. BW631)

Saturday, 4 October 2025

R.I.P. to the Sherbrook Inn parking lot!

 © 2025, Christian Cassidy


685 Westminster, now and proposed

There are at least a couple of large residential developments slated for West Broadway.

One is a four-storey, 21-unit, mixed-use building approved for the site of Howell Court at Broadway and Furby Street, (see the end of this post for more details), and a much more substantial building could be coming to the parking lot of the Sherbrook Inn.

The city's Committee on Property and Development will be asked at its October 9, 2025 meeting to approve a plan that would change the zoning on the Westminster Avenue lot to allow for a six-storey building with 86 residential units and one ground-floor commercial unit. 

If approved, the project could begin construction as early as January 2026.

The building is designed by Cibinel Architecture, whose recent projects include the WAG's Qaumajuq Inuit Art Gallery (2021) and the Transcona Library (2018).

The developer is Lotus Holdings Winnipeg Ltd. which has developed several buildings in partnership with Cibinel, including Solara Flats for the University of Winnipeg.

Here's Cibinel's FAQ about the proposed development. 

Civic Committee on Property and Development, Oct. 9, 1925 agenda

I wanted to look back at the history of the long-vacant lot, and what I found was a lot of houses!

The 1962 Henderson's Street Directory, the data for which would have been compiled in 1961, shows three properties on Westminster Avenue: 670 (Herbert Bassler); 689 (Ernest Butler); and 691 (Lucien Pagoot) and another six properties along Furby Street: 104 (Orest Venela); 106 (Abe Penner); 108 (Lloyd Thurston);  114( E. Bailey); 116 (Daniel Westbrot); and 120 (Mrs. K. Twyonak).

The 1965 directory, which would have been compiled in 1964 when construction began on the Westminster Motor Inn, as it was called back then, shows all nine houses are missing.

June 27, 1964, Winnipeg  Free Press

A few years back, I wrote a history of the Sherbrook Inn and in a preview article about the development in the June 27, 1964 edition of the Winnipeg Free Press, the architect's drawings shows development on that Westminster Street lot. It was described in the article as a multi-storey open parkade with a walkway connection to the hotel, which obviously never materialised.

Related:
A history of the Sherbrook Inn at my Winnipeg Places blog

Sunday, 21 September 2025

The life and work of Charlotte Galloway

 © 2025, Christian Cassidy


I have been working on a history of Howell Court at 661 Broadway and during my research came across a remarkable woman who lent her organisational abilities and fundraising skills to many prominent charities of her day. Her name has been forgotten to history and I didn't want her to get lost in a long post about the history of a building.

Here is more about Charlotte Elsie Galloway and her time in Winnipeg.


Bylaws of Toronto Orthopedic Hospital, ca. 1898

Charlotte Elsie Sanderson was born in Toronto in 1866 and grew up in Orillia Ontario where her father, Dr. G. W. Sanderson, practiced medicine. On August 29, 1898, she married  Dr. Herbert P. H. Galloway, an orthopedic surgeon in Toronto.

The same year as their marriage, the Toronto Orthopedic Hospital was established at 12 Bloor Street East. It was said to be the first hospital in Canada "devoted exclusively to the treatment of the lame, crippled and deformed".

Dr. Galloway was one of two full-time associates at the new clinic, a converted house, and he and Charlotte moved into the adjoining residence at 14 Bloor Street East. Charlotte was a founding member of the hospital's ladies auxiliary.

During their time on Bloor Street, the Galloways had three children: a son who died in infancy and daughters Muriel, born in 1897, and Ivadele, born in 1898.

661 Broadway in 2025

The couple moved to Winnipeg in 1905 so that Dr. Galloway could become the orthopedic surgeon for the Winnipeg General Hospital and the founding chairman of the Manitoba Medical College's department of orthopedics. 

The family initially settled at 187 Balmoral Street and in 1907, rented the former A. E. Ham residence at 661 Broadway that they would go on to purchase in 1913. 

The living arrangements were similar to Bloor Street with the house being both a family home and medical clinic. It was initially known as the Galloway Clinic and after a couple of extensions it became the Galloway - Gibson Clinic and eventually the Winnipeg Orthopedic Clinic. A separate building on Furby Street was the clinic's private hospital.

By 1918, the clinic had grown large enough that the family moved to 638 Wellington Crescent

1911 Census of Canada, Library and Archives Canada

The 1911 and 1916 census records show that the Galloways had two live-in servants at the house and, as the girls grew older, Mrs. Galloway had more time to dedicate to important charitable causes. 

A Winnipeg Tribune article noted that: "Mrs. Galloway, since coming to Winnipeg, has been identified with the most progressive philanthropic movements of her city."


January 30, 1922, Winnipeg Tribune

One prominent organisation that Mrs. Galloway dedicated herself to was the Anti-Tuberculosis Society. She sat on its executive for many years and served as president for six of them (ca. 1918 - 1923).

The organization was formed in 1908 to help establish and fund the provincial sanatorium at Ninette. After its construction in 1909, the society concerned itself with funding auxiliary items for patients, such as equipment and clothing.

One project Mrs. Galloway pushed for was the introduction of milk goats to the sanatorium. Goats took up less space than cows and would ensure the institution had a regular supply of nutritious milk. To prove that goats were well behaved and could be easily kept, she took two of them with her to the cottage in the summer of 1922 to look after.

In November 1922, the board agreed with her motion and goats were bought or the sanatorium.

April 30, 1914, Winnipeg Tribune
 
Mrs. Galloway served for seven years as secretary and two years as president (1914-16) of the local chapter of the Council of Women. The formidable organisation, which had about 8,000 members at the time, was involved in the establishment of the Winnipeg Children's Hospital, kindergarten programs and playgrounds.

During Mrs.Galloway's time as president, the Council had many activities on the go.

A Bureau of Work for Women was established from September 1913 to February 1914 that matched up 700 women with employers. An advisory censorship committee was created to advise existing censors on the suitability of films as being "family-friendly". A fur drive collected old pelts and coats that were shipped to Italy, where women used them to create jacket linings for Italian troops fighting in the Alps.

There was also the 5,000 name petition submitted to the federal justice minister seeking to exonerate Jennie Hawkes. The Alberta woman shot to death a woman she believed was having an affair with her husband and was sentenced to hang in November 1915. The council argued that a man in the same situation would likely not face any punishment.

In the end, Jennie's sentence was commuted to ten years in prison, which was disappointing for the group, but they did help save her life.

May 11, 1912, Winnipeg Tribune

Another group that Mrs. Galloway sat on the executive of and did extensive fundraising for was the Deaconess' Aid Society, a charity of the Methodist Church.

The society ran a maternity home on George Street for unwed mothers and other girls in trouble. It provided room, board, education, social activities and job training in the hopes that the women could lift themselves from poverty and not fall victim to prostitution.


January 15, 1917, Winnipeg Tribune

There were dozens of other organisations that Mrs. Galloway lent her organisational skills and fundraising abilities to, such as the Earl Kitchener Guild of the Children's Hospital and the Mothers' Association, which provided assistance for needy mothers and funded nursery programs, 

During the war, she was a member of the 203rd Battalion "Silver Lining" auxiliary that sewed and collected clothing and other items for members of the Winnipeg Rifles serving overseas and in POW camps.

Mrs. Galloway was honourary president of the Girls' Auxiliary of the Children's Hospital, a charter member of the Women's Canadian Club, and heavily involved with Broadway Methodist church. She once appeared before a civic committee advocating for the pasteurization of all milk sold in stores, and in June 1923 let her name appear in newspaper ads encouraging women to vote "no" in the upcoming referendum to end prohibition.

One newspaper article noted that "One of the chief interests of Mrs. Galloway was welcoming strangers to Canada. and Winnipeg in particular. She took particular delight in visiting them in their own homes and serving them in unobtrusive ways".

January 31, 1923, Winnipeg Tribune

The years 1922 and 1923 were ones of great change for the Galloways.

According to the Winnipeg Tribune, Mrs. Galloway had a stay in General Hospital in March 1922 but was soon "making a rapid recovery at her Wellington Crescent home."

In April 1922, the couple traded their house on Wellington Crescent with that of J. L. Bathgate, of the Scott Bathgate Company, at 34 Carlton Street. This was a smaller house with a much smaller property and signified he semi-retirement of Dr. Galloway and the declining health of Mrs. Galloway.

At the Anti Tuberculosis Society's January 1923 annual meeting, Mrs. Galloway announced that she was stepping down as president of the organisation after six years. In April, she stepped away from the executive of the Council of Women.

Mrs. Galloway, along with her husband and daughter Muriel, went on a tour to southern California and Hawaii in February 1923 and returned in early April.

The final official act of Mrs. Galloway appears to have been her attendance at a meeting of the Council of Women in late April 1923 to discuss "the liquor question". She did not speak but had a seat at the head table as past president.

July 9, 1923, Winnipeg Tribune

Charlotte Galloway died at the family home on Carlton Street on Sunday, July 8, 1923 at the age of 56.

A small funeral was held at the home two days later presided over by Reverend L. F. Dimmitt, pastor of Broadway Methodist Church, and a memorial service in her honour was held at the church the following week.

Galloway is buried in Elmwood Cemetery.

Monday, 8 September 2025

West End Builders: Loftur Jorundson

  © 2025, Christian Cassidy


L. Jorundson, July 3, 1910, Winnipeg Free Press

I have come across many Icelandic immigrants who got into the local building trade, such as VopniClemens, and Oddson after arriving in Manitoba. Whilst looking into the history of a house history on McGee Street, I came across carpenter Loftur Jorundson who certainly left his mark on the West End during its formative years.

Researching Jorundson was a bit of a challenge because of his name. Icelandic names are notoriously misspelled in English language sources like street directories, newspaper articles and even census records. For instance, his last name is spelled four different ways in street directories from 1895 to 1901. Icelandic sources use Loptur Jorundsson.

Here is what I could find about Loftur Jorundson:

1916 census shows the Jorundsons, minus Eirikur, on McGee Street with two lodgers.
(Library and Archives Canada)
Coming to Canada

Loftur Jorundson was born in 1861 at Hrisey, Iceland and came to Canada in 1888, likely first settling in the Lundar area. He married fellow Icelander Jónína Eiriksdottir in 1889 and they went on to have five sons: Eiríkur (b. ca. 1891); Sigtryggur (b. ca 1893); Jorundur (b. ca. 1895); Ingigunnar (b  ca. 1898); Thorhallur  (b. ca 1901); and Jens-Júlíus (b. ca. 1911).

Census records indicate that both Loftur and Jónína came to Canada ca. 1888, so they married quite soon after arriving. According to this community history, Jónína came to the Lundar region with her parents and siblings. It is unclear if the two knew each other in Iceland, met on the passage, or had a very quick courtship in Canada.


C. E. Steele's 1894 Birds Eye View of Winnipeg shows a sparsely populated West End. The streets would not be laid out formally like this for several years. Blue star is Portage, green star is Maryland, yellow star is McGee, purple star is Ellice.
(Full map at Manitoba Historical maps on Flickr

Coming to the West End

The earliest sign I can find of the Jorundsons in Winnipeg comes in the 1895 street directory, the data for which would have been compiled in 1894. Loftur is listed as a carpenter living at 625 Ness Avenue. By 1897, the growing family had relocated to Simcoe Street.

At the time, the West End beyond Maryland Street would not have been formally subdivided by the city into proper streets, sidewalks, and boulevards. Streets like Simcoe would have been little more than country lanes serving the pasture land, dairy operations, and horse stables that operated in the area.

When the family first arrived on Simcoe, it contained ten houses on it from Portage Avenue to Notre Dame, none with street addresses. By the time they got a street address in 1903, the Jorundsons were at number 372 (now demolished), and there were just 15 houses on the street. 

The Jorundson family moved to 339 McGee Street in 1904, a house that Jorundson built himself. In 1907, he built another at 351 McGee and this became the family home for years to come.


May 6, 1908, Winnipeg Tribune

Jorundson the Builder

Not long after arriving in the West End, Loftur Jorundson took his carpentry skills up a level and became a commercial home builder.

Between 1902 and 1906, he received at least 14 building permits in his name for houses on West End streets such as Toronto, Victor, Sherbrook, and Furby. Five of them were for houses on Jane / McGee Street between Livinia Street (now St. Matthews Avenue) and Portage. (it may have been more permits but due to the spelling of the last name might not appear.)

The home building permits end in 1906 for a time. Jorundson may have worked as a subcontractor for a developer of larger structures as he returns to building in 1908 with several much more ambitious building permits to his name.


Quo Vidis Apartments ca. 1976 (City of Winnipeg)

Jorundson's largest project was likely the 29-unit Quo Vadis Apartments on Qu’Appelle Avenue at Kennedy, just off Central Park. He took out the $56,000 building permit for the block which, was designed by architect David W Bellhouse, in May 1908. The three-storey plus full basement building measured 50 x 120 feet and was built of red brick with concrete trim.

This building was a bit of trailblazer as it was amongst the first wave of middle-class apartments built in the city. Prior to this, apartments were for the most part considered tenements, a place where poor people lived packed together to save on costs.

It was thanks to large group of Icelandic builders, developers, and architects, such as Paul Clemens and Thorstein Oddson, that the "three-storey walk-up" became respectable places to live and they built hundreds of them around the city. The Warwick Block, located a block from the Quo Vadis and constructed the following year, is often considered the first upscale apartment block in the city featuring balconies, fireplaces, a glassed-in courtyard, ad servants' entrances.


In 1909, came the five-unit terraced housing block on St. Matthews Avenue at Simcoe that Jorundson both designed and built using day labour. It stood until around 1980 and is now the Simcoe Street Tot Lot.

Diana Court ca. 2019

In  June 1911, Jorundson teamed up with fellow Icelander and architect Paul M Clemens for the 21-suite Diana Court apartments on Furby Street. The building was renovated in 2013 and 2015, but shut down in 2018 and again in 2024 by city inspectors for health reasons.

It is likely the only substantial Jorundson building that is still standing.

March 1, 1913, Winnipeg Free Press

Another permit was granted in September 1912 for an apartment on Maryland Street between Ellice and Sargent which he also designed. This was most likely the three-storey, ten-suite Loma Linda Apartments at number 516. It was just 25 feet wide by 100 feet long to fit onto a residential lot. 

"For rent" ads for the block end in 1977 and in 1980 there was mortgage sale of a lot of two apartment blocks - the Queens at 516 Maryland and the Loma Linda at 514. The Queens still stands but the Loma Linda or its address does not appear in "for rent" ads again and was presumably demolished soon after the sale.

The last building permits issued to Jorundson were for two dwellings on Fleet Street between Lilac and Aynsley in 1913, a departure from his West End stomping grounds. I also found a newspaper mention of him owning four houses on Vernon Road in St. James in the 19-teens.

After this point, mentions of Jorundson and budling permits end. As noted below, he could have gone to work for one of his sons, become a subtractor, decided to get out of the construction business and become a landlord as he appears to have owned and rented out several of the properties he constructed.

Attestation papers of John Jorundson, Library and Archives Canada

Wartime

The First World War would have been a stressful time for the family as their three eldest would have been old enough to volunteer. None of them did.

Newspaper records show that a “J. Jorundson” of 351 McGee Street applied for an exemption from the draft. It didn’t work as 24-year-old John (Jerundar), a carpenter like his father, was drafted and assigned to the #10 Engineers Depot.

It appears that John served his time in Canada and was dismissed in March 1919 as being “medically unfit” for service. He suffered from ongoing bouts of abdominal pain and injured his wrist whilst winding equipment which required him to wear a splint. (By 1919, the war was over so the bar for getting a medical discharge from service was much lower than it would have been a couple of years earlier!)

You can read John’s full war record here.

Another son, Sigtrigur, was drafted in June 1918 towards the end of the war. He was discharged weeks later after his medical examination found him unfit for service. He got his hand caught in a planing machine in 1912 (perhaps working with his father?) that left him with “impaired function of his right hand”.

You can read Sigtrigur Jorundson’s war record here.

Post War

1918 classified ad, WInnipeg Free Press

The Jorundson family stayed at 351 McGee until around 1918. They then disappear from street directories for a while, perhaps returning to the Lundar area or an extended vacation?

A classified ad that same year shows that son Eiríkur set up E. Jorundson and Co. carpenters and builders at a house the family rented a few doors down at 339 McGee Street, a house that Loftur Jorundson built in 1904 and presumably still owned. 

Loftur and Jonina reappear in street directories at 444 Maryland Street in 1920 and eventually returned to 351 McGee Street for a year.

Several members of the family then reunited at the Quo Vadis apartments in 1922 where Loftus is listed as the caretaker.

March 12, 1942, Hemskringla
 
By 1934, Loftur and Jonina moved to 555 Whytewold Road. Their son Julius moved into 583 Whytewold. These properties were likely semi-rural with large lots attached to them as the as neither of them exist today. The area became a suburban residential development in 1957.

Jonina Gorun Jorundson died at the family home in 1941 at the age of 75.

Loftur remarried Jóna Gíslason in 1944 at the age of 83! He died on March 5, 1952 at the age of 

Heimskringla, March 12, 1952

 Loftur Jorundson kept a fairly low profile. His name is mentioned in passing in newspapers but he was never quoted or interviewed, even in the Icelandic press.

Some of those passing mentions show that he was a trustee of the Icelandic Lutheran Tabernacle at Sargent and Furby in 1905 and 1906. He was on the board of the 21st annual Icelandic celebration at Elm Park in 1910. In 1911, he was fined $5 by the city for not cleaning up the horse manure at 339 McGee Street.

Google translation (Icelandic to English) of Heimskringla obituary:

Loftur Jorundsson died Wednesday, March 5, at the age of 90, at Princess Elizabeth Hospital. He was a native of Hrísey, Iceland, and was the son of Jörundur Jónsson and his wife Svanhyld.

He was born June 16, 1861. He moved to the West in 1888 and lived in Winnipeg most of the time since then, mainly engaged in house building. He was married twice. His first wife was Jónína Magnússon. They were married in 1889. She died in August1941.

Their children were 6 boys. Four of them are living. They are: Sigtryggur; Ingigunnar; Thorhallur and Júlíus. Those who are deceased are Eiríkur and Jorundur. Loft's second wife was Jóna Gíslason. They were married on January 1, 1944. She survives him and currently lives with her daughter Mrs. Gisel on Beresford St.

The funeral took place Saturday, March 8 from the Mordue Bros. funeral home on Broadway. Rev. Philip M. Pétursson officiated. Burial was in Brookside Cemetery.

Related:
351 McGee Street Winnipeg Places

Tuesday, 26 August 2025

Back to school a century ago

 
September 1, 1925, Winnipeg Tribune

This photograph appeared on the front page of the Winnipeg Tribune on September 1, 1925 as 37,024 children returned to school at Winnipeg's public school system. These boys were off to Carlton School on Carlton Street, where the True North Square is today. It operated from 1881 to 1929.

Valentine & Sons' Publishing Co., Ltd. from R. McInnes Postcard Collection

In the heydey of downtown's time as a residential neighbourhood there were two public elementary  schools that served as many as 600 students. The other, Alexandra School, operated from 1903 to 1969 and was located where the Convention Centre is now. 

Sunday, 13 July 2025

Victor Josselyn, WInnipeg's Dance Hall King

 © 2025, Christian Cassidy

While researching the history of 225 Fort Street, (read that story here), I came across Victor Josselyn, who played an important role in that building's early years as a dance hall. It turns out he was an investor and manager of several of Winnipeg's early dance venues, such as The Coliseum (1912 -  1917), the Alhambra (1917 - 1926), the Jubilee (1923), and Paradise Gardens (1931 -  ca. 1938).

Joselyn played an important part in the city's early entertainment history but not being connected to a theatre, he has been forgotten about over time. He was known as a charitable man, having hosted dozens of charitable events at his venues, especially during the First World War. 

Unlike some entertainment promoters, Josselyn kept a very low profile. He was rarely quoted in the papers about his venues or other activities and was never interviewed about his personal life.

Here's my attempt to find out more about his life and work.

Victor Eugene Josselyn was born in San Francisco and came to Canada around 1900 when he was in his early 20s. He does not appear in local street directories until the year The Coliseum opened in 1912, so he may have been wooed here by the partners in the Colosseum Amusement Company to be an investor and to manage the venue.

Though he was most associated with the dance halls, like most entertainment men he had other investments as well. For instance, he was the manager (and likely a part owner) of the Royal Albert Hotel circa 1920. His widow, Adelaine Josselyn, said in a 1976 interview that she first met Victor in 1926 when she was hired as a pianist at the Strand Theatre and he was a partner.

Josselyn managed The Coliseum until its closure in 1917. The ownership group changed and the hall reopened that fall as the Alhambra dance hall, later to be renamed Alhambra Dance Gardens.

During the Alhambra years, Josselyn also managed the Jubilee Dance Pavilion, a summer-only venue, in 1923. He may have been a part owner as the venue was around from 1919 to 1929.

In the late years of the Alhambra, sporting events took equal billing to the dances and Josselyn gained a good reputation as a wrestling and boxing promoter.

When the Alhambra property was sold to Diamond Taxi in 1926, Josselyn didn't continue with entertainment or sports. One newspaper article said he had relocated to England for a while, (the family that owned the building was the Goodmans of England.)

Josselyn reappears in local street directories in 1928, living at 35 Edmonton Street with no occupation listed. In 1930, he was noted as being "retired".

There was one more venture for Josselyn.

In 1931, he spent $75,000 to create  Paradise Gardens located on a 20-acre site just north of Kildonan Park. It contained a dance pavillon that could hold 3,000, a dining facility, and a 300-car parking lot. Over the first summer, lawn bowling, tennis courts, mini-golf, a shooting gallery, boat dock, market garden, swimming pool, and picnic area were added. 

The venue opened on May 24, 1931 with dancing each night until 2 a.m.. In true Josselyn style, he opted not to have an official opening ceremony for the park, telling a reporter that he preferred to let Winnipeggers see for themselves and decide if the park is worth it.

Paradise Gardens, which was billed as an amusement park, advertised regularly for the first couple of years. In October 1932 a classified ad read that due to poor health, contractors were being sought to run many of the activities and concessions. In October 1938, another classified ad appeared stating that due to poor health, the whole park was for sale.

Victor Josselyn died after a long illness at his home on Dunkirk Drive in July 1954 at the age of 74.