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The story of a Jewish-Canadian Second World War pilot who never came home

Sgt. Harry Black, centre, on leave in Cardiff, Wales, during the Second World War. (Lorne Winer photo)

A wooden statue shaped like an airplane wing used to sit in a place of prominence at Camp Naivelt, a Toronto-area Jewish summer camp. Camp staff built it over 75 years ago to honour the memory of a beloved sports director who everyone called “Blackie.”

He was a Canadian pilot who served with the Royal Air Force (RAF) in the United Kingdom and was killed in action during the Second World War.

According to a book about the camp titled A Future Without Hate or Need, the monument to Blackie was built in August 1943 by Sid Dolgoy, who was one of the founding members of the iconic Canadian folk group the Travellers, along with brothers Ben and Hy Chudnovsky and others, and was located beside an outdoor wooden stage.

“I remember the Blackie monument very well,” said Martin Schechter, a professor at the University of British Columbia in Vancouver.

“One thing for certain I remember is that the whole monument was in deep left field of the baseball diamond we used, and any hit to the monument was an automatic home run.”

I first learned about the Blackie statue in October 2019, when I was a guest speaker at the Yiddish Vinkl group, which meets each month at the Free Times Cafe in Toronto. Many of its members are alumnae of Camp Naivelt, a historic camp near Brampton, Ont., that opened in the 1930s and is still part of the city’s left-wing Jewish secular movement.

No one at Yiddish Vinkl remembered Blackie’s real name.

Although I spent years collecting the names and stories of the 17,000 Jewish-Canadians who served in the Second World War for my book, Double Threat, I had no listing for him.

Thus began my search. It was suggested that I reach out to Sharon Hampson, one of the stars of the children’s singing trio (now duo) Sharon, Lois and Bram, because her family had a cottage near Camp Naivelt. Hampson sent a note out to her Camp Naivelt circle and, with the help of former campers, some answers started to come in.

The Blackie monument at Camp Naivelt. Family unknown. (Courtesy Ester Reiter)

Jacob Bakan sent a link to a 2008 Globe and Mail obituary of Toronto lawyer Murray (Dusty) Cohl. The article says that Cohl got his nickname at Camp Naivelt and that he wasn’t the first camper to have that happen – the kids also gave Harris Black the nickname “Blacky.”

Frances Blugerman, 102, said that Black was her husband’s friend. She recalled that Black joined the RAF in 1940, trained as a pilot and went missing on a return flight from Germany in July 1941. “No one ever found out what happened to him,” she said.

A set of holiday photos

Decorated Toronto veteran Lorne Winer, 102, last saw the man he remembers as Harry Black when the pair shared an unforgettable week’s leave in Cardiff during the war.

The two had met in the street in Toronto before they enlisted. Winer said they were “acquaintances,” because they had gone to different high schools (Winer went to Central Commerce and Black went to Harbord Collegiate).

“He told me that he was turned down in 1939 for the Air Force here (in Canada) because he was Jewish,” Winer said. “He said he was going to work his way over to England on a cattle boat and join the RAF, which in fact he did.”

Winer enlisted a year later and arrived in England in December 1940.

Once overseas, Winer wanted to find out what had happened to Black, so he left messages for him at Canada House in London whenever he got leave.

“You put down your name, rank, serial number and military address to let anybody know, ‘I’m here and this is how you get in touch with me.’ Every time I went to London, I kept looking for Harry Black,” Winer said. “But I couldn’t find him.”

At the time, Winer was in the artillery, stationed near London. Black was an RAF pilot flying nightly raids at the helm of a Whitley bomber out of RAF Leeming with No. 10 Squadron. The base was in Yorkshire.

Yet fate would intervene to reunite the pair. Winer received an invitation from a successful Jewish furrier who lived in Cardiff. He didn’t remember the man’s name, but remembers that he sent his family to Toronto to escape the war, and that’s where the furrier’s wife met Winer’s mother. Addresses were exchanged and eventually the furrier contacted Winer and invited him to meet for tea at the Cumberland Hotel in London.

“I joined him there and he identified himself. And whom does he have in tow? Harry Black! I couldn’t believe it,” Winer recalled. The furrier was taking Black back to Cardiff for a week’s vacation and they invited Winer to join.

There was plenty of room for the Canadians in the furrier’s six-bedroom home, since his wife and four children were in Canada.

Winer and Black spent time at the seaside resort of Porthcawl and snapped numerous photos, including one of Black dressed in white pants, a white open-necked shirt and a linen jacket.

The Wall of Honour at Harbord Collegiate Institute, Toronto. (Ellin Bessner photo)

Another of Winer’s photos shows Black posing with the furrier’s Welsh neighbours. The woman is smiling, but Black looks serious. “The entire week, there’s Harry Black, who was a happy guy, who’d smile and so on, a handsome boy, down in the dumps … fearful of what would happen if he were captured by the Germans,” Winer said.

Black told Winer he had already changed his dog tags to ones stamped “OD” for other denominations, rather than the “H” for Hebrew. Winer remembers Black predicting that he was not going to survive the war.

“He kept saying to me he’s not going to make it back. All his colleagues had been killed and he kept repeating that to me the entire time. He said he was a dead man,” Winer said. (No. 10 Squadron lost nearly 1,000 crewmen in the war.)

Black had already survived a harrowing raid in May 1941, while bombing Hanover. His plane was dropping bombs when it became coned, or trapped, by a group of German anti-aircraft searchlights. Being silhouetted in the light made the Whitley an easy target and German night fighters moved in to attack, strafing the plane with bullets. Black was listed as the second pilot on board. While wartime reports don’t say who was at the controls, they managed to make it safely back to base.

After Winer and Black thanked their host in Cardiff and returned to duty, Winer sent the vacation photos to be developed, which he said took a long time. When he got them, he mailed them to Black’s base.

“The letter came back to me, ‘Missing in Action,’ and that was the end of Harry. That’s my story of Harry Black and it’s a very sad story,” Winer said.

While Winer is certain their Cardiff trip happened in 1943 and that his friend went by the name Harry, not Harris, British wartime records show a Canadian pilot named Sgt. Harris Black serving with the RAF. The National Archives lists Black’s final mission as taking place in July 1941 – a full two years earlier.

Black’s four-man crew was sent out at 10:42 p.m. on July 7, 1941, to bomb Osnabruck and the railway yards. According to Harris’ file, their plane was last heard from six hours later. The bomber is presumed to have crashed into the sea off the east coast of England, while en route back to the base.

The government reported pilot Black and the other three crewmen all as officially missing in August 1941.

Black has no known grave, but he is commemorated, along with 20,000 other missing Allied aircrew, at the Runnymede Memorial in Surrey, England.

After the war, Winer sent his vacation photos to Black’s family in Toronto, but he never heard from them and doesn’t know if the letter was ever received. As to whether Black is the same man who went to Camp Naivelt, Winer isn’t sure.

What Winer does remember is that his friend’s father ran a millinery store.

The 1940 Might’s Toronto City Directory (a type of phone book) does indeed list a Barnett Black, who owned Black and Cairn Millinery and lived at 194 Concord Ave. with a Harris Black, who’s listed as having been employed as an office clerk with the Adam’s Furniture Company.

The Harbord War Memorial

The walls of the Memorial Hall at Harbord Collegiate high school are lined with double rows of framed black and white portraits. They show former students in their military uniforms who were killed during the First and Second World Wars. A photo of Sgt. Pilot Harris Black is located just outside the auditorium doors. It bears the inscription “Missing Over Germany,” and the date July 8, 1941. With his high forehead, prominent smile and wavy brown hair parted to the left, he looks like the pilot who is posing in the photo that Winer took in Cardiff.

Another photo, this one at Harbord’s in-school museum, shows a student named Harris Black, with the word “Blackie” on the caption, wearing a suit and posing with a young woman on his arm. It was taken at a school track and field event. The person in the photo also looks exactly like the pilot in Cardiff.

Graduation programs for the years 1937 and 1938 have a Harris Black’s name on the list, showing that he finished his required four years at Harbord and went on to complete Grade 13, though his grades weren’t great.

Entries in the school’s yearbook during the late ’30s list a player named Black on the junior rugby team during the 1935-36 school year. An H. Black took first-place honours for the under-17 age group in the city high school track meet in 1937 in discus throwing, pole vaulting and shot put. It makes sense that he could have been hired as the sports director for Camp Naivelt.

Close to 700 students and staff from Harbord served in the war. There are 52 names of those who did not come back – including Harris Black – engraved on a stainless steel sculpture outside the school. The Harbord Club’s busy alumnus group raised the funds and commissioned fellow graduate Morton Katz to design it. Of the names on the H-shaped structure, more than half are Jewish students.

“People said Jews didn’t fight for their country,” said Murray Rubin, 89, explaining one of the motivations for his Harbord Club undertaking the sculpture project, even though more than six decades had passed since the end of the war.

At that time, “about 85 per cent of the school was Jewish,” Rubin said.

The unveiling ceremony in 2007 attracted a lot of media attention and one sister, who is believed to be Blackie’s next of kin, showed up.

“I remember that when the memorial to the students of Harbord who died in the WW2 was dedicated I saw Maxine (formerly Black) there crying,” wrote Cheryl Tallan, a former Naivelt camper and Jewish history academic in Toronto. “I think that she lived out of town because I hadn’t seen her for many years and I haven’t seen her since.”

“They were fighting for us”

It would mean a lot to Lorne Winer to find his friend’s relatives, even after all this time. In the meantime, the hunt for Blackie has led to a bit of closure, of sorts.

An email request I sent to the small Jewish community of South Wales looking for the name of the wartime Jewish furrier was successful. Tony Blasebalk, who is in charge of the Jewish burial board of the Cardiff United Synagogue, tracked down the family, named Dubow, who had sent a wife and children to Canada during the war. The furrier’s only remaining child, Leslie Dubow, is a retired lawyer who lives in London.

Dubow recalls being seven, and sick with the measles, when his determined mother, Jeannie, wrapped him in a blanket and boarded a ship in Liverpool in the summer of 1940, together with her three other children, and departed on a perilous journey across the Atlantic.

“We were refugees in 1940 when it looked like Hitler would invade,” said Dubow, 86, in a telephone interview. His father, Harold Dubow, then 53, remained in Cardiff, continuing to run his fur wholesaling factory. He also served as a warden in the country’s Air Raid Precaution force.

Leslie Dubow remembers his mother being unhappy in Toronto, as money was very tight and she had no close family there. She made some friends in a ladies’ knitting circle, which is where he believes she likely met Winer’s mother and sent his address on to her husband.

The Jewish community in Wales opened their homes to visiting Jewish personnel stationed in the area, according to Dubow. He doesn’t remember specifically hearing about Lorne Winer or Harry Black, but he knows his family home would have had many bedrooms to spare when he was in Canada. Winer confirmed that they and the furrier were alone in the house.

In July 1943, Dubow’s mother decided she had had enough of Toronto and somehow brought the kids back home to Cardiff, dodging German spies in Spain and surviving two air raids along the way. When they arrived back in Wales, Dubow clearly remembers his family opening their home to deployed Jewish servicemen.

“I can remember Americans and Canadians coming Fridays for Shabbat,” Dubow said. “A couple of them gave me candy.”

As to why his father would have gone out of his way to host Winer and Black, Dubow emphatically stated that, “The country was at war and they were fighting for us, so we had a duty to look after them.”

The story of his father’s kindness to two Jewish-Canadian men who had volunteered to protect England certainly struck a chord with Dubow. It was especially meaningful when he learned how his childhood home was the last place that Lorne Winer would see his friend Black.

“Tell Lorne we share his grief,” Dubow said.

Dubow was able to deliver that message to Winer personally, when I helped them connect by telephone.


The hunt for Blackie is not over. Anyone with information can contact Ellin Bessner at [email protected] Bessner is a journalism professor at Centennial College and the author of Double Threat: Canadian Jews, the Military and WWII. Special thanks to those who assisted in the research, including British historian Martin Sugarman, Joey Jacobson’s War author Peter J. Usher, Sharona Brookman, Ester Reiter, Jacob Bakan, Sol Hermolin, Bev Freedman and Jackie Kay of the High Wycombe Society in the U.K.

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Ellin Bessner is the author of Double Threat: Canadian Jews, the Military, and World War II.