James (Jimmy) Kay, is a man well-known in Canada for his monumental success with Dylex Ltd., – the now-defunct billion-dollar clothing consortium – as well as his Jewish philanthropic endeavours.

But a recent discovery by Elaine Kay, Jimmy’s wife of 50 years, prompted her to tell a different, less-known story about her 91-year-old husband – one that paints him as a decorated World War II hero.

The story begins when Elaine, 75, invited a relative of hers, a war veteran, to dinner at the Kays’ opulent Yorkville home months ago.

“He said, ‘Wasn’t Jimmy a captain? He was very famous in the war. He got a million medals.’”

At his urging, Elaine called Veterans Affairs Canada in Ottawa for a package containing his medals, information about where and when he served, and a copy of his attestation papers, all of which arrived last summer.

According to his attestation papers, Winnipeg-born Jimmy was 18 years old and a slight 143 pounds when he enlisted with the Canadian Forces in September 1939.

By 1942, Jimmy was serving as a lieutenant in the Royal Canadian Army Service Corps (RCASC). He later became a captain and saw active service in Britain and northwest Europe until he returned home in 1946.

In recognition of his service, Jimmy was awarded a number of medals, including the 1939-45 Star, the France and Germany Star, the Defence Medal, the Canadian Volunteer Service Medal, the War Medal 1939-1945, and the General Service Badge.

But it is a letter from Jimmy’s troops –which had been filed away for decades until it was stumbled upon a few weeks ago – that has become the Kays’ most prized possession.

“We had an office on Bloor [Street], and we dismantled it a few weeks ago. There was this portfolio that had a few things from the war, and in it was this letter that he was talking about all these years,” said Elaine, speaking for Jimmy, who suffers from dementia.

She said that although he never spoke in detail about his war service, he often talked about a letter he received from his troops when he served as captain of the 36 Canadian Army Troops Composite Company in Holland in 1946.

The letter, written on a card in calligraphy, said, “A small token of appreciation to the ‘old man,’ an officer, a gentleman and a regular guy. From his boys, 36 Cdn. Army Troops Comp. Coy R.C.A.S.C.”

“When we found this note, it was so emotional… I was crying and crying,” Elaine said.

Along with the letter, Jimmy was given a Dutch guilder note, signed by each member of his company.

“He was always for the people. He was not snobbish. Anyone could come to him. He was a regular guy. It’s unreal, unbelievable that there would be this kind of history in our possession,” she said.

Although she didn’t know many details about Jimmy’s war experience, the RCASC website indicates that Jimmy’s unit was an administrative and transport corps that provided support to Canadian soldiers throughout their training. They moved supplies, including rations and ammunition, to the frontlines for the northwest European and Italian campaigns.

His group was one of a number of RCASC units that supplied ammunition for Operation Totalize, the offensive launched by Allied troops of the First Canadian Army during the later stages of the invasion of German-occupied Western Europe.

Throughout the interview, during which she leafed through pages of documents, photo albums and other memorabilia, Elaine displayed an admiration for her husband that was palpable.

It could be noted in the way her voice would rise when emphasizing his many accomplishments as an entrepreneur, a philanthropist, a community leader and a war hero; and more subtly when she lovingly brushed his hair to make sure he looked his best for a photo.

“He was always a great leader, which translated into the companies he ran,” Elaine said. “He was outstanding.”

Following the war, Jimmy established himself in the plastics business before moving to Toronto, marrying Elaine in 1963, and raising four children.

In 1964, he moved into the world of retail by purchasing small businesses, starting with Fairweather, a women’s fashion retailer.

But it was a meeting in 1966 with clothing manufacturer Wilfred Posluns that propelled Jimmy into a decades-long partnership that made billions in profits.

In his prime, Jimmy also served a number of Jewish community organizations in various roles, including the Jewish National Fund of Canada, Baycrest Centre, the Canadian Council for Christians and Jews, UJA Federation of Greater Toronto and the Weizmann Institute of Science in Israel.

At its peak in the 1980s, Dylex, an acronym for Damn Your Lousy Excuses, was a company that operated 2,700 stores in North America, including Fairweather, Tip Top Tailors, Big Steel and Suzy Shier.

By the early 1990s, the number of Dylex stores in North America had dwindled to about 1,000.

It was then that Kay walked away from the once-untouchable clothing empire. In 1997, he purchased Hudson Bay Wholesale and remained a successful businessman, a feted Jewish community leader and a philanthropist.

“He was a wheeler dealer. He was unbelievable. He was very handsome. He was everything,” Elaine gushed.

But it is this most recent discovery of the letter and the guilder note that has her seeing her accomplished husband in a new light.

“Suddenly to realize… the significance of what he did… And to think Jimmy Kay was just a youngster… he was just a kid.”