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Phyllis Lee Dana came into the world on October 5, 1936, and left it peacefully at home in her sleep on May 17, 2026. Predeceased by her parents Maurice “Lippy” Benson Lipson and Ida “Billie” Lipson née Cohen, she is survived by her husband of over 71 years, Nathan Dana, their children Karen (Harry Havey) and Marshall (Andrea Miller), grandchildren Jessee (Nathaniel) and Josh Havey, her younger brother Edward Lipson (Carol), nephews Michael (Ceren) and Daniel (Doree), beloved cousins, many lifelong friends, and the hundreds who fondly remember her as their kindergarten teacher, “Mrs. Dana”.

An exceptionally talented singer and performer from a young age, she gave up a scholarship to study opera at New York City’s Curtis Institute of Music to marry and start a family with her true love and best friend, Nate – a decision she never regretted for a moment. As expressive and animated off the stage as she was on it, Phyllis was a pillar in Winnipeg’s Jewish community, known for her nearly 30 years of teaching in the Jewish day school system, as a vocal soloist and synagogue choir member, and as an active member of several community organizations.

Phyllis offered a receptive warmth and curiosity to all she met, possessed a keen intellect and a sharp wit, was a gifted writer, poet, and storyteller, prolific baker, voracious reader, lover of butterflies, and made a mean brisket.

Despite being 89 years old, her passing was still unexpected by the remarkable family, community, and legacy she leaves behind, and she will forever be deeply missed by all who knew and loved her.

Because you loved to write in rhyme / Your words so thoughtful and divine / Here’s some for you, straight from the heart / Now from us you’ve had to depart / We cannot thank you near enough / For what you were to all of us / For teaching us to love and sing / And all those children all those things / For how to best articulate / And speak the things most think (not say) / Your voice forever will live on / In stories, teachings, and in song / Your work is done, the time has come / For you to rest, our precious one / Your memory a blessing be, Love you forever, 

Phyllis Lee!

Harold Diamond passed away at the age of 90 on May 12, 2026 at the Simkin Centre in Winnipeg, Manitoba.

Harold was born in Winnipeg in 1935, and spent his childhood and teenage years in Fort William, Ontario. He was the son of Dr. J. Diamond and Nellie Diamond, and brother to Leatrice Cohen, Dr. Naomi Diamond, Gloria Nitzburg, and Selma Stein.

He attended the University of Manitoba, earning a Bachelor of Arts in Political Science. During those years he joined the ZBT fraternity, eventually serving as President in 1957. Harold completed the science prerequisites required for dentistry and was accepted into the University of Manitoba Dental School. While studying dentistry, he joined the Alpha Omega Dental Fraternity and became its President in 1959.

In the spring of 1960, Harold received a research grant from the Federal Research Council to work under Dr. John Spouge, head of Oral Medicine at the University of Manitoba Dental College. Their groundbreaking research examined patients with rheumatic fever and identified links between dental procedures and recurrence of the disease. The work ultimately contributed to recommendations in both Canada and the United States for preventative antibiotic treatment prior to dental procedures for at-risk patients – protocols that went on to influence many other areas of medicine.

Dr. Harold Diamond graduated in 1963 and opened a successful dental practice in Windsor Park. and became a respected leader in dentistry. He served on the Winnipeg Dental Society Board and was President in 1975-76. He also joined the Manitoba Dental Association Board and later served as President. . As President of the MDA in 1980, Harold prepared an important submission to the federal government regarding the lack of dental services in rural Manitoba. His work demonstrated the challenges rural dental practices faced and helped shape discussions around dental care accessibility in the Province.

During Harold’s time at the University of Manitoba, he met the love of his life, Paula Roseman. Harold and Paula were engaged in the spring of 1958 and married on August 4th, 1960. Their daughter Maureen was born in 1964, followed by their son John in 1967.

Together they built a beautiful life filled with love, partnership, family, and adventure. Harold was deeply devoted to his family, and nothing in his life mattered more to him than the people he loved, especially Paula. He placed everyone else’s needs before his own and loved his family with his whole heart.

Harold was an exceptional student with a brilliant mind, a champion chess player, and a thirst for knowledge. His passions were politics and history and later in life became an accomplished bridge player. He loved music and had a smile that would light up the room.

A devoted husband, a loving father and grandfather, a cherished uncle, colleague, mentor, and friend. Harold was deeply loved and will be profoundly missed.

Over the years, Harold faced many health challenges and remained deeply grateful for the loyalty and support of his associates, his office manager Joselyn Badiou, Dr. A. Miller, and the cardiac care team at the Cleveland Clinic.

Harold is survived by his wife (Paula Diamond), his daughter Maureen Diamond (Andrew Marquess), his son John Diamond (Heather Diamond) and his grandchildren, Samantha, Daniel, Benjamin, Matthew, Alex and Jake.

Donations can be made to the Harold and Paula Diamond fund at the Jewish Foundation of Manitoba.