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JAMES (JIM) ALEXANDER SHEPHERD
Date of Passing: May 26, 2025
Send Flowers to the Family Offer Condolences or MemoryJAMES (JIM) ALEXANDER SHEPHERD
It is with love and gratitude that we announce the sudden but peaceful passing of James (Jim) Shepherd on May 26, 2025, at the age of 92. Jim leaves behind a legacy of kindness, curiosity, and quiet strength that shaped the lives of those around him.
He was predeceased by his parents, Harry and Barbara; sisters, Isabella (Stan) and Eileen (Bob); brother-in-law Paul Campbell; son-in-law Johnny; and many lifelong friends and extended family.
Jim will be lovingly remembered by his children: Craig (Jennifer) and grandchildren, Morgan and Ryan (their mother Joanne); Mark (Dawn) and grandchildren, Chloe, Lena (Ryan), and Jayne (Kyle) (their mother Carla); Daphne (Dennis); Cynthia (Chris) and grandchildren, Robbie and Hunter; and Susanne and grandchildren, Charmaine (Elvis), Lauren, Hope, and Cheyanne. He also leaves behind their mother and his former wife Ruth Campbell who with Jim maintained a respectful and caring relationship that prioritised family.
Jim is also mourned by his closest friend Mina who, with Mina’s family, held a special place in his heart, as well as many relatives and other dear friends.
As a father Jim was positive, supportive and engaged. His children fondly remember summers spent at Sandy Hook and West Hawk Lake with boat rides and campfires. The family’s pop-up trailer road trips in search of KOA campgrounds and swimming pools across Canada and the US, helped spark a lifelong love of travel and adventure in his children.
Jim’s 11 grandchildren will remember their grandpa as always willing to join in on whatever was up. A favourite activity of the grandchildren was baking with grandpa - particularly at Christmas. He always showed an interest in how they were doing as they moved through their various stages of life.
Jim was also a proud great-grandfather who cherished time with the little ones and always made sure to capture those moments in photographs.
Jim’s passion for travel continued throughout his life. There were countless special trips over the years which included family members and Mina in various configurations to enjoy concerts, spa weekends, and touring from Europe to Palm Springs and Las Vegas. He was always eager for the next outing and happy to share stories from his travels.
Jim’s working life began in the family business, Chalmers Auto Truck and Body Works Limited, where he worked alongside his grandfather (James Chalmers) and parents for over 25 years. After the sale of the business in 1979, he fulfilled a lifelong goal of attending university, earning a Bachelor of Social Work degree. He went on to have a 20-year career working in a number of Winnipeg personal care homes where it was clear he had found his calling, to the benefit of the residents. His work often included performances involving lively piano playing and singing.
Music was a lifelong passion. Jim played the piano and had a rich, resonant singing voice that he shared through church and community choirs, including the Winnipeg Philharmonic Choir. At nine years old, he joined the Winnipeg Boys’ Choir - an experience that remained meaningful throughout his life. At age 91, he returned to perform as an alumni in the choir’s 100th anniversary celebration, a moment he treasured. He also had the chance to sing with choirs in Europe and specifically in Belgium with an international choir commemorating the liberation of Northern Europe.
Jim’s energy was extraordinary. He remained physically active to the end, swimming laps at the YMCA several mornings a week. He enjoyed tending his yard and garden with great pride and care.
Jim made friends wherever he went, he had a gift for conversation and genuine curiosity about others. He valued neighbourly connections, including regular lunches with “the guys from the block,” friendships that spanned over six decades.
He also contributed to his community in meaningful ways - volunteering at local shelters and, more recently, was Vice-President of the North East Winnipeg Historical Society Inc., where he shared and celebrated the stories of East Kildonan and Elmwood.
Jim had a deep appreciation for life. He often expressed how grateful he was for the love and closeness of his large family, he gave great hugs so you knew it. He looked forward to birthdays, holidays, and everyday visits - especially if dessert was involved!
As he said at his 90th birthday celebration in 2023:
“Life so far has been a full and interesting journey.”
On his final day he raked the lawn and did some gardening. He went in for a rest where he slipped away while sitting in his chair - hat and gardening gloves on. A beautiful end to a wonderful life.
In lieu of flowers, please donate to either the Winnipeg Boys’ Choir https://winnipegboyschoir.ca/donate/ or to the Siloam Mission https://www.siloam.ca/ in honour of our father as these organizations were very important to him.
A private family service for interment will take place in the summer.

As published in Winnipeg Free Press on Jun 07, 2025
Condolences & Memories (10 entries)
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Craig, Mark, Daphne, Cynthia, Suzanne and families. A note from the Chrustie family from Green avenue and long time friend of the family since the 60’s. Wanted to pass my family Condolences from our family to yours. Many fond memories back in the 60’s and 70’s hanging at your house with Mark and our other friends. Your family and father was remembered for kind hearted and respectful - and obviously cascaded into his children. Mark - big hug to you bro - talk soon and keep in touch. Calvin Chrustie - the Chrustie family / past and present with hugs. - Posted by: Calvin Chrustie (Friend of Family) on: Jul 31, 2025
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I only got to know Jim these past few years at the early morning swims at the Y. I always enjoyed our conversations and looked forward to hear how he was making out gardening. He was an inspiration and I will miss seeing him. - Posted by: Sean Moran (Friend from the YMCA) on: Jul 29, 2025
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Jim was a force to be reckoned with at Siloam Mission. Jim spent just under 1000 hours in the kitchen prepping and serving meals to community. Jim would walk in for his shift - always on time -don an apron, check the daily task list and immediately ask how other volunteers and kitchen staff were doing before he got to work. Jim shared that the Siloam kitchen was one of his happy places and it felt good to give back. Jim's compassion, his sense of humour and commitment to helping others experiencing homelessness spilled over to other kitchen helpers. Jim made friends easily and always offered a kind ear. Jim made a huge difference in making Winnipeg a better place. Thank you, Jim! Siloam Mission will not forget you. - Posted by: Margot Ross (Senior Manager, Siloam Mission) on: Jun 16, 2025
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I had the privilege of getting to know Jim over the last several years through our connection with the Winnipeg Boys' Choir (WBC). Jim took his role of being a member of the WBC Alumni Chorus seriously, always a pencil in hand at rehearsals and checking in with the conductors after each rehearsal to ensure he knew exactly what was being asked for musically. A highlight was meeting Jim early in the morning of May 1, 2024, for our live radio interview on Classic 107.1FM. Jim arrived to the interview with prepared notes, and spoke fondly and proudly of his time with the WBC. Quotes from that interview were included in this May's anniversary concert program, along with a photo of the choir from the 1940s (supplied by Jim) that featured him as a young boy. We at the WBC are all richer for having known this gentleman. My sincere condolences to Jim's family. - Posted by: Carolyn Boyes (friend) on: Jun 12, 2025
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I met Jim a decade ago when he signed up to sing with the alumni chorus for the Winnipeg Boys’ Choir’s 90th season. His tales of taking the streetcar to rehearsal downtown on his own or with a friend when he was a very young child added so much to our story, and it was a joy to chat with him. I was delighted when he came back to sing with an alumni chorus for the past couple of Christmases, including our 100th this past season. He fully intended to sing with us again this coming Christmas. He was a lovely man, and we will miss him. - Posted by: Nicola Spasoff (friend) on: Jun 09, 2025
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What a beautiful tribute! Your family was such a big part of my teenage years. I feel blessed to have known all of you, including your dad who was probably annoyed by Sue and my antics! My condolences to your entire family. Thank you for letting me be part of your lives! - Posted by: Robyn Henke (Starr) (Friend) on: Jun 08, 2025
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To Craig, Mark, Daphne, Cynthia, Suzanne, and family. My family, Bill, and I are so sorry to know of your dear Dad's passing. All that was described of his character and his life in this obit, was written with certain truth and love. You have all shared in a large part of his 92 years and added joy and fully enriched his life and surely made him proud, and he to you, and to your lives. Know that you all didn't fall far from the tree. We wish you good thoughts and strength each day forward. Friends, Jill and Bill Palmer and the McWhinney family. - Posted by: Jill Palmer (Friends) on: Jun 08, 2025
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A beautifully written tribute to a beautiful man. Jim and I shared a special and meaningful friendship, when we were both older students in the Social Work program at the University of Manitoba. We spent many hours discussing program expectations, the courses we taking, upcoming tests or exams, and our plans for what kind of work we hoped we do after graduation. Jim was always kind, considerate and supportive during our time there. After graduation we remained friends for a while, but life got in the way and after a couple of years we lost touch. Jim was truly a special man. - Posted by: April (Friend) on: Jun 08, 2025
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In my childhood, "Uncle Jim" was a gentle presence with a ready smile, and, whenever I crossed paths with him as an adult (usually at various arts events), he was always smiling and a delight to talk with. My late parents' lives were enriched greatly by through their lifelong and precious friendship with Jim. It makes my heart glad to know that he lived a vital life doing what he loved to the last. Craig, Mark, Cynthia, Daphne and Suzanne, you and your families have my sincerest sympathies. I am thinking of you at this difficult time and hoping you will find comfort from family and close friends. - Posted by: Janice Finlay (Family Friend) on: Jun 07, 2025
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Mr. Shepherd was a family friend of my mum's and I spend many a New Year's Eve celebrating with him at our home and that of the Derraugh's home across the street. He was a most gentle, kind, and caring person - alway curious about what one was doing. He was truly a fine gentleman. He will be dearly missed by many in the Elmwood/EK community. My deepest condolences to the Shepherd clan. Rest in Peace Mr. Shepherd. - Posted by: Grant Clark (family friend) on: Jun 07, 2025