Eileen Jennings

January 27, 1958 – January 29, 2023

It is with heavy hearts we say goodbye to our wife, mom, granny and friend.  Eileen passed peacefully on January 29, 2023, surrounded by family. 

Left to mourn Eileen is the love of her life Kevin Wilton; her children Sean, Adam, Christopher (Micar); her grandchildren Dakota, McKayla, Keon and Aleaha; Kevin’s children Shelby (Matt) and Brooke (Christine).  She also leaves behind, her siblings, John (Donna), Richard (Sinead), Mary (Allan), Michael (Carol), Kathleen and her brother in law Howie as well as numerous nieces and nephews, cousins, aunts and uncles.

Eileen was predeceased by her parents, John and Mary Shortt and her sister Margaret O’Neill.  

Eileen moved to Winnipeg in 1978, this is where her boys were born and the place she called home.  Her door was always open, her ear was always open and she would dole out her words of wisdom and advice to anyone who needed them.  She made quite a few lasting friendships with people who became like family to her (you know who you are).  

She started her career in the insurance business as an administrative assistant, through hard work and determination to build a better life for her and the boys, she worked her way up the corporate ladder.  She was getting ready to retire from her Regional Vice-President role, when she became ill. 

Eileen loved spending her weekends at her seasonal site at Netley Resorts in Petersfield, the deck was always a welcoming place for anyone walking by, and if you stayed long enough, a dance party might break out.  She will be missed.

Eileen and Kevin loved life, they enjoyed traveling together, especially for winter getaways to Cuba.  Although they didn’t have as many years together as they wanted, they packed a lifetime of memories into those years.    

A Celebration of Life in Eileen’s honor is planned for February 12th @ 2:00 pm at Inn at the Forks Ballroom.  Speeches will begin at 3:00 pm.  Bring your dancing shoes, Eileen wanted a party and that is what she will have.

Eileen has requested in lieu of flowers, donations to Siloam Mission in her memory. 

Family and friends are invited to share memories and condolences on Eileen’s memorial page by using the comment field below.

Please note: there is a delay between when a comment is submitted and when it appears on the memorial page.

36 thoughts on “Eileen Jennings

  1. Stuart and Donna Tulloch

    Our condolences 🙏 are prayers are with you and your family Sorry for your loss

  2. Brian Power

    Rest In Peace Eileen
    You will be missed by so many. It was nice to meet you at the campsite.

  3. Garry Schwartz

    Eileen will truly be missed. Leanne and I enjoyed our time with Kevin and Eileen. Our weekends in Winnipeg, at Petersfield or in Kenora were filled with stories and some beer, always enjoyable.

  4. Charlene Fitch

    We are sending our condolences to Kevin and the family. We are so sorry to hear of the sadness of losing Eileen. We only had a short time of getting to know Eileen. But she made a lasting impression on me. I loved her Sass. My first time meeting her she says to me ” you’ll fit right in here” Of course there was a sassy undertone. Haha. I loved the fact I could walk over and sit on the deck to have conversation. We are going to miss you Eileen. The Netly community won’t be the same without you. 💔
    Charlene Fitch and Bob Barnes

  5. Teri Patey

    I am so very sad for your loss Chris, you and your family are in my thoughts.

  6. James Mc Sherry

    Rest in peace, Eileen. The Mc Sherry family.

  7. Crystal lavigne

    My beautiful friend,

    Our relationship has been the longest one for me. You had a huge part in helping me to become the person I am today. When I’m near you it always feels like I am with my sister. Quiet was not uncomfortable around you.

    Hope the stars are as beautiful where you are as they are from where I stand. Can’t wait to hug you once again.

    Family, my deepest sympathies for the loss of the one you call Hon, Mom, Sister, and granny.

    So Come On Eileen!!! Start leaving those dimes. Love you more than you will ever know. 💙

  8. Tricia

    I’m sorry we never got to visit Winnipeg. But grateful we got to catch up at knoebels. You made your mark on so many. You will be missed more than you could imagine. Love and prayers for our family.

  9. Marlene & Frank Hunter

    Our deepest condolences. RIP Eleen

  10. Wynn Sweatman

    I am saddened to learn of Eileen’s passing. She was fun to work with, knowledgeable and always helpful. She maintained friendships within the insurance industry forever. Her laugh was contagious.

  11. Ken and Donis

    It is often hard to find the right words at a time like this. May you find peace, comfort, and all the love you need in the days to come.

  12. Susan and Wilgus Back

    Rest in peace Eileen. Our thoughts and prayers are with you and the family. Grateful that we were able to get together at the last cousins reunion.

  13. Terri Botosan

    The HUB Family will miss Eileen tremendously. She was an absolute pleasure to work with. A woman with a passion for the industry and such a kind heart and caring nature.

    My thoughts are with Kevin and her entire family at this very difficult time.

  14. Lynda Falloona

    Sending our condolences to the entire family
    May you now be free of pain and joining all your loved ones that went before you
    Rest easy Eileen
    The Falloona Family

  15. Dave Thompson

    I was very saddened to learn of Eileen’s passing. I first met Elieen when we were competitors and had a somewhat prickly relationship. But Eileen’s humor and transparency opened the door for what became an enjoyable and fruitful collaboration over time. Her sense of humor, her wit and her laugh always made me smile. Through the experience of both the work world and “trailer life” she also had a close connection to my spouse Darlene who passed in 2018. Eileen’s connection to my wife made me feel even closer to Elieen and it makes her loss feel even more keen. She was a true gem. Ken and family, my heartfelt condolences to you all in this difficult time.

  16. Brian Kirk

    I am sorry to learn that Eileen has passed away, & I am sorry that she & I lost contact with each other. She worked hard to create a career for herself and a good life for her boys. She & I had many conversations about raising sons, & Eileen was devoted to her 3.
    I will remember her well, & I wish all her family all the strength needed to cope with this loss.
    Brian Kirk

  17. Tannis Leach

    …fun to work with, knowledgeable, definitely of value, AND SASSY! Our paths crossed many times over the years in the insurance industry – including my first day of work in the industry in 1995. I’ll miss you old friend!

  18. Marianne Ferrer

    My life was blessed through Eileen’s support and friendship. I will treasure all she’s done and her memory is a keepsake from which I’ll never part.

    Rest in peace my friend. You will be missed.

    Sending her family my love and prayer for strength in the days ahead.

    -Marianne Ferrer

  19. Mary Feng

    I was very saddened to learn of Eileen’s passing. She was such a big help for me when I started with Hub. I really enjoyed working with Eileen and learned so much from her.
    My heartfelt condolences to her family in this difficult time.

    Eileen, may you rest in peace.

  20. Marien Mortel

    Thank you, Eileen! I feel honoured that I had the opportunity to get to know you. Do know that I’m blessed to have you in my life. You may be gone from my sight but never from my heart. I will for sure miss you. Guide from above.

    Sending healing prayers and comforting hugs to the family.

  21. Bir Inder Behl

    Eileen, you and your knowledgeable thoughts will always be missed. My deepest condolences to the family. May her soul rest in peace !

  22. Ray Mutuc

    Rest in Peace Eileen. Thanks for all the support you have given me throughout my career, it will never be forgotten. My condolences to the Jennings family 🙏.

  23. Emily Cressman

    My condolences to Eileen’s family. She was a beautiful soul who will be missed dearly. I only met her a few years ago at her paradise away from home at camp but all time spent around her was positive and nice! Kevin, she will be with you everyday in your heart and watching over you. You’re a strong person and your friends and family are here to support you, always.

  24. Paul Davis

    I had the pleasure of working for Eileen. She was a caring boss and a friend. She will be missed.

  25. Lorraine Gauthier

    Kevin and Family, I have known Eileen for almost 20 years…. a delightful person who provided support when needed at anytime ! She was kind, smart, caring and always had a smile…She had a contagious laugh that I will always remember…. Eileen treated Associates/Brokers in the Insurance Business with the utmost respect…I will miss her ! Thoughts and prayers go to ALL the Loved Ones she has left behind, Sincerely, Lorraine Gauthier

  26. Prescila Rivero

    Condolonces to the family.
    Eileen is very nice person, very approachable with a kind hearted heart. She is very easy to deal with as a corporate leader & as a friend. We will truly missed her.
    Thank you very much Eileen for all the help you have given to us.

  27. Sun Life

    Sun Life extends its significant thanks to Eileen and sincere condolences to her family.
    Eileen was an advocate for Sun Life, always great to deal with and a source of insight in that part of the country, something very valuable to us.
    Some of us met Eileen’s family, at a Daystar conference and were impressed by such fine people. We will miss you Eileen and thanks for being an advocate for Sun Life for almost two decades.

  28. Norm Delongchamp

    A ray of Sunshine that will be slightly dimmed and sorely missed up at her little piece of Heaven at Netley Creek…Rest In Peace Eileen and keep the patio open Kevin 🧡

  29. Jenny C

    Adam, I’m so sorry for your loss. <3

  30. Lesley

    My condolences to your entire family. Take care of each other ❤️

  31. Maria Desousa

    My dear beautiful friend may you fly with the angels no more pain RIP you will be miss. My deepest condolences to the Family 💔🙏

  32. Michael van Lierop

    From the team at NOW, our sincerest condolences to the family. Eileen was a generous, caring and attentive professional who knew how to make light of things – and laugh, something so often lacking in this all-too-serious financial and insurance industry. She was a breath of fresh air. Eileen will be missed. May she rest in peace.

  33. Marisa Yurkiw

    Eileen was a beautiful person who was kind and hospitable to everyone she met. She had a contagious laugh. I am so glad I got to know her. Netley will never be the same My deepest condolences to her family. My thoughts and prayers are with you all at this very difficult time. R.I.P, Eileen. You will be deeply missed. 💔💔

  34. Dawn & Pat Gilbert

    We are so very sorry to learn of the loss of you sister. Our thoughts and prayers are with your family at this very difficult time.

  35. Wendy Williams

    The best gift I have ever received was the gift of Eileen’s friendship. We met at a time when we each became single parents of very small children.
    Eileen’s friendship was a gift that will last forever. Eileen was the strongest, most giving, loving and wise woman I’ve ever met.
    She guided me when I needed to be guided, she offered wisdom and words of confidence when I needed them most.
    She was an incredible mother to her son’s and other mother to my daughter Jennifer who will forever absolutely adore her.
    There is so much more I could say about the impact this beautiful lady made in our lives. But those who know and love her know what it is to call her “friend”.
    Thank you Eileen, I couldn’t have made it without you.
    I will always love you and your boys.
    I will always cherish your friendship.❤️

  36. David Griffiths

    I am saddened by the loss of Eileen.
    She was a proud individual determined to make a better life for her boys and herself. Eileen earned the respect and admiration of many in the life insurance industry. She became a go-to-person for those who needed product assistance.
    Kevin and family are experiencing the greatest loss.
    I had the opportunity to experience their Netley summer home with them and their friends. What a memorable weekend!
    She will be missed.

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