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CYNTHIA (LYNN) LESSARD
Born: Jan 24, 1954
Date of Passing: Mar 07, 2026
Offer Condolences or Memory Make a donation to Winnipeg Humane Society
CYNTHIA (LYNN) LESSARD
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.
As published in Winnipeg Free Press on Mar 14, 2026
Condolences & Memories (8 entries)
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I went to school with Lynn starting in grade 8 and into high school. Kathy and I were good friends with Lynn and Harold back in the day. Lynn was quite humorous in her own way. It took me a while, but I finally learnt to save my breath in any disagreement with Lynn as she was going to win. Like Jocelyn we got our updates from Al on how Lynn was doing. After loosing Harold, Lynn spent much of her time devoted to her family. That’s what she wanted to do and I respected that. Our condolences to the family and Al. - Posted by: Ron & Kathy Phelps (Friend) on: Mar 16, 2026
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On behalf of the United Fire Fighters of Winnipeg, I extend our heartfelt condolences to Bryan, Chrissy, and the entire Lessard family on the loss of Lynn. Lynn will always hold a special place in the hearts of Winnipeg firefighters. Her connection to our fire service ran deep, and even through profound loss she remained a constant source of strength and support for our firefighting community. The pride she carried for Harold, for Bryan, and for the fire service was something everyone who met her could feel. On a personal note, I will always remember the conversations Lynn and I shared. She was such a kind and warm person. Whenever we spoke, we would often talk at length, and I always left those conversations knowing she truly cared. Her kindness and genuine warmth will always stay with me. Please know that the entire Winnipeg firefighting family stands with you and is keeping your family in our thoughts during this difficult time. With sincere sympathy, Nick Kasper President United Fire Fighters of Winnipeg - Posted by: Nick Kasper (Family Friend) on: Mar 16, 2026
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Dennis and I offer our deepest Condolences to her family 🙏 to you all at this difficult time 😞 - Posted by: Christine Magus (Sister in law) on: Mar 15, 2026
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I was fortunate enough to work for/work with Lynn when she was the manager of the Major Investigations Program with Service Canada. Lynn was a great leader and truly cared about those she worked with and made sure everyone was treated with respect. I feel ordinate to have know Lynn and my condolences to her loved ones. God Speed - Posted by: Dave Q (Co-worker) on: Mar 14, 2026
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Lynn was my manager for a few years when I worked in I&C. At first I was a little intimidated by her, but we developed a friendly rapport in fairly quick order and it wouldn't be unusual for her to call me at my desk and ask me to come see her in her office. No one likes to be beckoned to see the boss, but it turned out she just wanted to say hi and engage in some friendly banter (and quite a few jokes). Lynn could be all business one minute, and cracking jokes the next. Her sense of humour really came through in her weekly 'Survivor' update emails that many in the office looked forward to reading. I still have the baby blanket Lynn purchased for me from a shop in Gimli when I was pregnant. She was always checking in on me to see how I was feeling and I was touched by her caring and generous spirit. Sincere condolences to all of Lynn's family and friends. - Posted by: Andrea H (Coworker) on: Mar 14, 2026
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Joy, Doug , Rob & Family ....My sincere condolences in the loss of your sister Lyn. - Posted by: Taylor Brian (Old neighbour) on: Mar 14, 2026
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So sad to read of Lyn's death. We were quite good friends in our early teens through twenties, until we both got married and then seemed to go off on our own ways. Lyn and I met in Grade School and our friendship continued through High School at CCI and on. Although I hadn't seen her in many years, I did run into Al more recently and he updated me on how things were going in her life. My deepest condolences to her children, Bryan and Crissy, and to Al and of course Morty. - Posted by: Jocelyn (Friend) on: Mar 14, 2026
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I met Lynn through a mutual friend, Annabelle Stokes. I thoroughly enjoyed the short time I spent with Lynn as I loved her sense of humour! We had many great laughs together! My very deepest condolences to Lynn's family. - Posted by: Louise Bloomfield (Friend) on: Mar 14, 2026
