CYNTHIA (LYN) LESSARD

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CYNTHIA (LYN) LESSARD

January 24, 1954 – March 7, 2026

Cynthia “Lynn” Lessard (née Chaikoski) passed away peacefully on the evening of March 7, 2026, surrounded by family at Health Sciences Centre in Winnipeg, Manitoba, at the age of 72.

Lynn was born on January 24, 1954, in Winnipeg, Manitoba, to Michael and Minnie Chaikoski (Michalyshyn). She grew up in Charleswood alongside her three siblings, Joy (Keith), Rob (Angie), and Doug (Sharon) until October 1974 when she married Harold.

She will be lovingly remembered by her two children, Bryan (Heather) and Chrissy (Lawrence). Lynn was a proud grandmother to Dylan and Aubrey and always enjoyed hearing about their many successes in sports and activities. She enjoyed watching them splash and play in the backyard pool during the summer months and often reflected on how much Harold would have loved to know them. Lynn also recently became a step-grandmother to Sophie, Michael, Jack, and Claire. Although she did not have as much time with them as she would have liked, she loved the many updates Chrissy shared about their dancing, hockey, and the family adventures they enjoyed together.

Lynn was predeceased by her beloved husband, Harold Lessard, who lost his life in the line of duty with the Winnipeg Fire Department in 2007. Despite this profound loss, Lynn remained deeply connected to the fire department community and continued to be a proud supporter and advocate. She co-founded the Lessard Nichols Scholarship fund after Harolds passing and found great reward in supporting the next generation of fire fighters. One of her proudest moments came in 2008 when her son Bryan joined the Winnipeg Fire Department, proudly following in his father’s footsteps.

Despite being squeamish with anything related to the medical field, Lynn supported Chrissy through her nursing education and was incredibly proud when she became a charge nurse in the Emergency Department. When Harold would come home from work, Lynn would ask about his day. Like clockwork, Lynn was left feeling queasy with the stories he had shared and would say “I’m sorry I asked.” In later years, she shared the same sentiment about Bryan and Chrissy’s stories from the hospital and fire hall. Still, she listened anyway - often with a grimace - because nothing mattered more to her than hearing about the lives of the people she loved.

Lynn spent the majority of her career with Service Canada, where she formed many lifelong friendships before retiring as a manager in 2013. Known for her warmth, humour, loyalty, and generosity, she was someone people naturally gravitated toward and never hesitated to provide quick witted commentary.

Lynn had a deep love for animals and found immense joy in supporting the Winnipeg Humane Society. She especially loved watching the many birds that visited the backyard - Harold’s pride and joy - particularly during the summer.

She also leaves behind her longtime loyal friend Al, and their beloved cat, Morty.

The family would like to extend their heartfelt gratitude to the staff at Health Sciences Centre for the incredible and dignified care Lynn received, especially in her final moments.

Lynn will be remembered for her quiet strength, unwavering support of her family, her generous spirit, and the pride she carried for those closest to her. She was someone who always stood up for the people she loved, and because of that, she helped shape them into stronger people. She was, and will always remain, an inspiration to those she leaves behind.

In leu of flowers, donations can be made to STARS Air Ambulance or The Winnipeg Humane Society. Any future Celebration of Life will be announced at a later date.

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As published in Winnipeg Free Press on Mar 14, 2026