A Life's Story

July 25, 2026

The gift of song

Beloved matriarch, kindergarten teacher lived a musical life

By: Gabrielle Piché

Phyllis Dana faced a choice: leave Winnipeg to study opera at a prestigious Philadelphia school, or marry the man she loved.

She chose the latter.

Now, her Juno-winning granddaughter cherishes a Happy Birthday voicemail sung by Phyllis. Three generations of Dana women — Phyllis, her daughter, and granddaughter — would sing in Winnipeg’s prominent Jewish spaces. And hundreds of Manitobans know the matriarch as their kindergarten teacher.

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                                A mother, grandmother, and kindergarten teacher, Dana was a lifelong lover of music.

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A mother, grandmother, and kindergarten teacher, Dana was a lifelong lover of music.

“My mom said, ‘A sheet of music won’t keep you warm at night,’” Karen Dana recalled.

Phyllis had met Nathan — whom she’d be married to for 71 years — in 1953, after graduating high school.

Around that time, she was offered a full scholarship to the Curtis Institute of Music in Philadelphia, Pa. The organization touts itself as America’s most selective music conservatory. It accepts four per cent of applicants.

Phyllis had taken classical voice lessons. She knew the stage; she performed in musical theatre at St. John’s High School, in Winnipeg’s North End.

Her family moved to River Heights before Phyllis’s final year, but she refused to transfer to the nearby Kelvin High School — she insisted she’d graduate with her friends.

Instead of walking roughly three minutes, she bussed for 20.

“That was very Baba,” said Jessee Havey, Phyllis’s granddaughter. “If she had her mind made up about something, it was like, ‘OK, we’re just going to stand back.’”

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                                A young Phyllis Dana in front of the Bieldy Apartments in 1943.

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A young Phyllis Dana in front of the Bieldy Apartments in 1943.

That fiery spirit drew Nate to Phyllis, said Havey, 43. (Havey spent hours interviewing her grandparents, considering herself lucky to have them alive during her adulthood.)

The duo met through mutual friends and would go on double dates with different partners. Eventually, Nate turned to his friend and asked him if he intended to marry Phyllis.

As the lore goes, the friend said no, and Nate said something like, “Well I intend to.”

The friend gave the go-ahead for Nate to date Phyllis. She’d applied to the Curtis Institute before meeting Nate; her acceptance letter and decision came later.

She and Nate settled in the North End. They married when she was 18 and had Karen a year later.

In another three years, Phyllis would birth her son Marshall and, following his entry into school, find what Havey deemed another “calling” — kindergarten teaching.

“Baba spoke like a kindergarten teacher regardless of whether she was in front of a room full of five-year-olds or not,” Havey said. “She was so animated and articulate.”

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                                Dana, age 17, with Nate, age 21, at the Copa, Winnipeg, 1954. The couple would marry a year later.

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Dana, age 17, with Nate, age 21, at the Copa, Winnipeg, 1954. The couple would marry a year later.

A true performer, Phyllis led songs with actions, emphasizing Yiddish words as she stood — four-foot-11 and one-quarter — in front of her tiny audience.

She worked in Winnipeg’s Jewish day school system, at I.L. Peretz School and, later, the Talmud Torah-I.L. Peretz Folk School. She helped establish all-day kindergarten, according to Karen.

She spent nearly three decades teaching.

In early days, Phyllis worked without a teaching certificate. She went to university for her designation in her mid-30s and took night courses once private schools required the education.

Karen was studying to be a social worker at the same time. She’d accompany her mom to the University of Winnipeg, doing homework while Phyllis took courses. Karen calls it “special time” together.

The women would also sing together — so often that they would ad lib songs and physically point to indicate who would take high and low tones.

Phyllis sang in synagogue choirs most of her life. As a senior, she worried she’d lose her pitch and sound like a “drowning cat.”

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                                Dana, aged 24, performing in High Button Shoes at Rainbow Stage in 1961.

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Dana, aged 24, performing in High Button Shoes at Rainbow Stage in 1961.

“She never sounded like a drowning cat, but she was very concerned,” Havey said. “She sang beautifully until the very end.”

Last year — at 89 years old — she sang with her daughter and granddaughter at a Holocaust remembrance event held by the Gwen Secter Creative Living Centre.

“I was singing with my parents and my baba from the time I was born, basically,” Havey said. “I think it made her so happy that I took a knack to that.”

Havey won a Juno Award with her folk fusion band the Duhks in 2006, under the roots and traditional album category. The next year, the group was nominated for a Grammy for best country performance by a duo or group with vocals.

Havey now has a Winnipeg-based kid’s music group — Jessee Havey and the Banana Band — that Phyllis saw perform.

“I always kind of felt like, knowing that she gave up this music career, that I was kind of carrying the torch for her,” Havey said.

Phyllis and Nate would be “front and centre” at shows, thrilled to watch their granddaughter take the stage, Karen added.

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                                (From left) Nate, Phyllis, Karen, and Marshall Dana, Winnipeg, 1976

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(From left) Nate, Phyllis, Karen, and Marshall Dana, Winnipeg, 1976

“They worked together,” Karen said of her parents. “They loved each other and they liked each other, and that was really, really important for both of them.”

Both volunteered. Phyllis was involved with a number of groups, including Gwen Secter’s board. Nathan, then a retired garment industry worker, drove for Meals on Wheels, among other volunteer jobs.

Karen was inspired by her parents. She’s since been recognized for her own volunteerism — with a King Charles III Coronation Medal and a Manitoba 150 medal.

One of Karen’s best friends, Rabbi Allan Finkel, led Phyllis’s funeral earlier this year.

He was a regular at the family’s house during high school lunch breaks; it was next door. He remembers the smells of home-cooked meals and that neighbourhood kids often stopped by to the use the washroom.

“(Phyllis) really had that touch to make people feel loved, cared for and safe,” Finkel said. “You always felt good when you were in her presence.”

Her eyes would smile, he added: “She was tiny but she had this aura around her, presence around her which was much, much bigger than her physical size.

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                                Phyllis receiving her Bachelor of Arts from the University of Winnipeg in 1980. She would later earn her Bachelor of Education from U of W, as well.

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Phyllis receiving her Bachelor of Arts from the University of Winnipeg in 1980. She would later earn her Bachelor of Education from U of W, as well.

“She’ll really be missed.”

Phyllis died peacefully in her sleep on May 17, her family said. She was 89 years old.

gabrielle.piche@winnipegfreepress.com

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