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JANIE KUPSKAY
Born: Jan 07, 1956
Date of Passing: Jan 26, 2025
Offer Condolences or Memory Make a donation to CancerCare Manitoba Foundation
JANIE KUPSKAY
Janie Kupskay, born on January 7, 1956, passed away peacefully on Sunday, January 26, 2025, with both of her beloved daughters by her side.
Janie was a devoted mother to Alyce (Nigel) and Sara (David), whose love and dedication brought her immense pride and joy. She cherished her role as a grandmother to Braxton, Kai, Bridget, Charlotte, and Tripp, treasuring every moment spent with her grandchildren and creating memories they will hold in their hearts forever.
She was predeceased by her loving parents, Fred and Alyce, and her brother, Mike, whose presence she carried with her throughout her life.
Janie dedicated her career to the River East Transcona School Division, where she worked as a teacher and guidance counselor. Janie made a profound difference in the lives of her students. Her passion for helping others was evident in her commitment to supporting students through life’s challenges, always offering a listening ear and heartfelt guidance.
Janie’s warmth, strength, and love touched the lives of everyone who knew her. Her kindness, quick wit and genuine compassion will be dearly missed but fondly remembered. A heartfelt thank you to her sister, Jo Al, and Janie’s close friends for their unwavering support during the final months of her life.
The family will honour Janie’s memory in a private gathering.
In lieu of flowers, they ask that donations be made in her name to the Winnipeg Pet Rescue Shelter or CancerCare Manitoba.


As published in Winnipeg Free Press on Feb 01, 2025
Condolences & Memories (17 entries)
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My sincere condolences to Janie’s family and friends. - Posted by: Jack Hardman (School) on: Mar 25, 2025
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So sad to lose my cherished friend sharing good and bad times together, when happy and sad, having fun or being miserable, listened when we thought ourselves intelligent and talked nonsense, laughed and cried together, understanding when we knew what we were doing and when we made mistakes, believing and supporting each other and always ready to share thoughts kept in the ‘vault’. Blessed to have had Janie as my lifelong friend and will miss her dearly. - Posted by: Janis Klassen (Lifelong friend) on: Feb 12, 2025
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Childhood classmate who ended up living across the street from each other on Malcana Street. Watched the children grow up, coffee partied and went to our neighbourhood playgrounds. Very sorry to hear Janie suffered with cancer and now the family has to go on without her. She will definitely be watching from above and be rooting for you all! Sincerely, Carla Riediger - Posted by: Carla Riediger (Friend and neighbour) on: Feb 07, 2025
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A beautiful family your daughter made what would she do without you. You will be missed - Posted by: Peter Thomas (Old friend) on: Feb 05, 2025
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So very sad to hear of Janie's passing. We had such fun times together in our youth - from frolicking in the waters of Laclu and Echo Bay, holidaying in Hawaii, laughing, joking, sipping wine, talking, etc.. Janie was always full of laughter, bubbly and fun to be with. My heart goes out to her girls. May she rest in peace. - Posted by: Janet and Greg Potter (Old, old friends) on: Feb 05, 2025
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When I moved out of my family home in north end and went to finish grade 11-12. She counseled me and got me through toughest years when I was 16 dealing with trauma. She got me to focus on school and graduate after I given up due to the move out. I want to say she was the best person and counseler the school had and like a mother. Never forgotten and forever missed love u Mrs. Kupskay!❤️🕊️❤️ - Posted by: Jacob Robinson (Student) on: Feb 04, 2025
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My sincere condolences to the family. I am forever grateful for her dedication and commitment to supporting and providing guidance to my son through his high school years. She was one in a million. May she rest in peace.🙏 - Posted by: Linda Warywoda (Parent of prior student) on: Feb 03, 2025
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I am so sorry to hear about Janie's passing. I worked side by side in the resource/guidance area with her for many years at River East Collegiate. She supported me as a colleague many times! Thank you, Janie! Rest in peace. - Posted by: Helen Macneil (Colleague) on: Feb 03, 2025
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I am a former student of Mrs. Kupskay. She made such a difference in my world…..I am so saddened to have come across this. I am now a teacher myself, and part of that is because of her. My condolences to her family. - Posted by: Jen Barrie (Student) on: Feb 02, 2025
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Sending condolences to all of Janie’s family and friends. I worked with Janie in the RETSD. She was an incredible support to so many at risk youth going above and beyond to help them in any way she could. I enjoyed my time collaborating with her to help students and loved her kindness and non-judgmental empathy. - Posted by: Nikki Humenchuk (Former co-worker) on: Feb 02, 2025
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I started at River East Collegiate from 2012-2015! My junior high guidance councillor introduced me to Ms.Kupskay before I started high school! When I met her she was amazing! I struggled with my mental health all through out high school, and she was always there for me! Being in and out of hospitals she was always at my meetings! Trying her best to figure out ways to help me! I remember she would take be out for when it was my birthday too! I remember she was such a loud person too! She did everything loud! She would laugh loud, sneeze loud, and especially when you could hear her coming down the hallway with those keys jiggling! She has made a huge difference in my life! May you rest in peace! I love you Ms.Kupskay! Thank you for everything! - Posted by: Bianca Pasaluko (Former Student (Class Of 2015)) on: Feb 01, 2025
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Our deepest condolences. - Posted by: Chris Light and Family (Friend) on: Feb 01, 2025
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Janie was such a compassionate person. Very loving Grandmee. My deepest condolences go out to you all. Big hugs to you all. 💝. Marlene - Posted by: Marlene Dunn (Friend) on: Feb 01, 2025
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It is with great sadness I read of Janie’s passing. My heart goes out to her daughters, family and friends. Janie was such an amazing person. She could light up a room in seconds. Janie’s dedication to students was like no other. She advocated for her students and her sincere compassion was like no other. Both of my children benefited from knowing her. Together Janie we had many wonderful times. Whether it was over coffee or a glass of wine, the laughs were plentiful. There is no doubt Janie you are in heaven looking after many dogs. Love you my sweet friend. Rest in peace. ❤️ - Posted by: Debra De Graeve (Friend) on: Feb 01, 2025
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Rip Mrs Kupskay, 43 years ago she was my typing teacher at MMCI. She was my favorite class, next to Art and I can still type 70 words a minute because of her teaching. I am very sorry for your loss, condolences to her daughters, she was much to young. - Posted by: Roxanne Hudson (former student) on: Feb 01, 2025
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Many years ago, I so appreciated Ms. Kupskay’s help when my son was having trouble at school. The students respected her and the parents were lucky to have her support. Peace to her family. - Posted by: Andrea (Parent of student) on: Feb 01, 2025
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My sincere heartfelt Condolences to Janie’s family and dear friends. I had the pleasure of working with her at RETSD and she was a force. Staff and students were fortunate to know her and to be supported by her. I am deeply saddened by her loss but remember so very warmly all the great conversations we had about students and life. Rest easy Janie. Eugene Hayduk. - Posted by: Eugene Hayduk (Colleague) on: Feb 01, 2025

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