Eldon Maurice Montgomery

Born ~ September 27, 1943

Date of Passing ~ September 24, 2026

With sadness and relief, we announce the peaceful passing of Eldon Montgomery on September 24, 2026, at the age of 82.

Eldon Maurice Montgomery was born on September 27, 1943, in Maryfield, Saskatchewan, to Maurice and Rachel Montgomery. He grew up on the family farm with his older brother, Irvin, where he learned the value of hard work, helping friends and neighbours, and making fun out of not very much. He carried those lessons throughout his life, along with his love of sports, family, and community.

From a young age, Eldon worked hard at home on the family farm, enjoyed school and recess with his friends, looked forward to Saturday nights in town, and playing hockey. He was never the biggest guy on the field or ice, and this meant he had to be quick, both in speed and wit. Eldon graduated from Maryfield School and started work at the bank in Virden, Manitoba. His favourite part of this first job was that he got to carry a gun when they went to pick up the money from the train each week.

After a year at the bank, Eldon decided to enroll at Brandon College and complete his teacher training. Upon completion, at just 19 years of age, Eldon moved to Russell, Manitoba, where he began his career teaching a Grade 6 class at Major Pratt School. In 1966, he left Russell and returned to Brandon College, where he would earn his Bachelor of Education and meet the love of his life, Joan Gilmour, beginning a partnership that would span 59 years and be filled with family, friendship, laughter, and shared memories. Following their marriage, Eldon taught for one year in Shilo, Manitoba, before they returned to Russell, where they built their life together and raised their children, Jodi, Jill, and Jon.

During the early years of raising their family, Eldon (aka Sugar Bear) played for the Russell Rams hockey team, helping capture an Intermediate B Championship. Long road trips, evenings at the rink, and celebrations with teammates and friends became cherished memories and an important part of small-town life.

Eldon was a great dad. He supported his children in everything we did, always there to listen, offer advice, and cheer us on. He brought us along to whatever team he was coaching when we were little and spent countless hours coaching all of us in the sports we played. Family time was filled with camping, ski holidays and road trips, made possible in part by the many “extra” jobs dad took on, from painting houses to refereeing hockey. He was our biggest supporter, our trusted listener, and the best dad we could have asked for.

Eldon was a lifelong educator. Over the next 35 years, he served as a teacher, coach, mentor, counsellor, vice-principal, principal, and superintendent. He was highly respected by his students and colleagues and made a lifelong, positive difference in the lives of many.

Eldon believed strongly that sports were as important to a young person’s education as academics. He spearheaded many sports programs and teams at Major Pratt School and dedicated countless hours to coaching and refereeing football, hockey, volleyball, track and field, and supporting young athletes. Among his proudest accomplishments were coaching provincial championship football and hockey teams. For Eldon, sports were about much more than winning—they were about teamwork, friendship, commitment, and learning how to be part of something bigger than yourself.

Together with the 1969-70 Major Pratt School nine-man Football Team, Eldon was inducted into the Manitoba Football Hall of Fame. Many members of this team came back to school at Eldon’s coaxing to play football and left with a bonus high school diploma.

Eldon’s pride in and dedication to the betterment of his community of Russell inspired him to lead and support numerous local initiatives throughout his life. He served as a town councillor, a devoted member of the Lions Club, and coordinator of Communities in Bloom, where he spent hours weeding flower beds around town and chatting with whoever passed by. He also held the role of President of the Russell Golf Course and was a tireless fundraiser for the Russell Community Centre, Russell Swimming Pool, and Russell Arena. Known for his enthusiasm, generosity, and gift for bringing people together, Eldon was also a master of ceremonies extraordinaire, lending his voice, spirit, wit, and charm to many community events and celebrations. Golfing, curling, hiking and biking at Clear Lake were favourite “free time” activities.

After moving to Winnipeg in 2011, Eldon brought the same spirit of service and community involvement to their new home. He proudly served on his condominium board and took great care in ensuring the flowers and grounds were always beautifully maintained. Family remained at the center of his life, and he could almost always be found cheering from the sidelines at his grandchildren’s sporting events around the province or on the Island. Whether at a ball diamond, gym, or hockey arena, Grandpa/Little Bubba was their biggest supporter and rarely missed a game or event. His unwavering encouragement, pride, and presence meant the world to his grandchildren, who knew they could always count on seeing their grandparents in the crowd and receiving a much-anticipated phone call from Grandpa after each game.

Eldon is survived by his wife, Joan; his children, Jodi (Ward), Jill (Todd), and Jon (Darla); his grandchildren, Kate, Hugh, Leif, Riley, Jaxon, and Lennon; his brother, Irvin (Marilyn); sisters-in-law Carol Anne Trowell (George) and Lynne Bailey (Doug); and many nieces and nephews.

He was predeceased by his parents, Maurice and Rachel Montgomery, and his infant son, Mark James Paul.

Eldon will be deeply missed by his family and friends and all those whose lives he impacted. His family takes comfort in knowing that he is now at peace.

“Always Hoe to the End of the Row”

A Celebration of Life will be held on Wednesday, October 7, 2026 at 1:00 p.m.

at St. Boniface Golf Club, 100 Rue Youville, Winnipeg.

In lieu of flowers, donations can be made to The Alzheimer’s Society of Manitoba,

CancerCare Manitoba Foundation or Dying with Dignity Canada.