DYLAN RAYMOND OLSON

Dylan Raymond Olson passed away on September 29, 2025 at Health Science Center in Winnipeg at the age of 28 yrs. 

He was predeceased by his brother Shane Davidson and father Dale Olson, along with many other relatives he loved dearly. 

Dylan is lovingly remembered by his mother Cecilia McKay, his brother Eugene McKay, sister Rainbow Chartrand (Curtis Flett husband) and their children Jaida Chartrand and Cobain Flett, Sister Desiree McKay (Trevor Ledoux partner) and their children Jasmine Ledoux, Tristen Ledoux, Sister Summer Leech (Mason Braun partner), and their son Kemsley Braun. 

Dylan was born at St Boniface Hospital in Winnipeg, MB on July 12, 1997. he spent his entire life living in the City of Winnipeg, MB. He was treaty to Minegoziibe First Nations (Pine Creek). He attended Ralph Brown Elementary School and then St.Johns High School. As an adult he worked with his mother Cecilia at the RBC convention Center and he worked with N’Dinawemak and he was also a Sabe peacewalker and in each of these roles Dylan met many friends who became like family to him. He had a positive impact on many lives. 

In addition to these roles Dylan enjoyed helping and participated in traditional ceremonies. He was especially good at being a Shkabe and fire keeper at Sundance. 

Dylan always loved his video games but he liked to especially sit around and spend quality time with friends and family. He was funny, caring, considerate, and had a passion for helping others in need. He would give the shirt off his back to anyone if they needed it. He was also artistic and could do anything he set his mind to. 

The family wants to say Meegwetch (thank you) to N’Dinawemak, Community Helpers United, Kekinan, Bear Clan Patrol, Minegoziibe First Nations, Elders Clayton Antoine and Barbara Campbell, Kristen McKay and the many drummers and singers and community members who came to support the family with prayers, food, firewood, and whatever the family needed. Meegwetch to everyone who sent condolences, made financial contributions, and helped with other resources the family needed during this difficult time. 

A funeral service will be held Saturday October 11, 2025 at 10:00a.m. - 4:00p.m. at Cropo Funeral home, 1442 Main Street in Winnipeg.

Dylan Raymond Olson was born July 12, 1997 at St Boniface hospital in the presence of his sister Rainbow and cousin Sherry, who was always like a big sister to Dylan. He had the most perfectly round head and beautiful dark eyes with his mother’s eye lashes that most girls have to pay to get. Dylan was such a good baby and easy to care for. Rainbow use to put him in his carrier and take him shopping at Polo Park often and he never cried. People use to give her weird looks probably thinking she was a teen mom. Rainbow was so proud of her new baby brother and loved to show him off. Everyone loved Dylan, from the moment he joined the family he stole the show. He was his moms baby boy and we all knew it. No one would mess with him without mama bear showing up ready to defend her cub. 

Dylan had a unique bond with each of his siblings. He was blessed with two big brothers. Eugene was his big brother, his keeper and his protector. All Dylan needed to do was call Eugene and without a thought Eugene was out the door and on his way to find Dylan to take care of business. They spent many years together looking out for each other and taking care of their mother Cecilia, or stressing her out. They were a little wild at times, it’s no secret that out of Cecilia’s children they were the ones who loved to party. But through thick and thin they always had each others back, at times as best friends and also as brothers.

Dylan also had an older brother Shane Davidson who had suddenly passed away in 2020. One of the regrets Dylan talked about was not having more time with Shane and not having as much memories with him. Shane had moved away for most of Dylan’s childhood and they hadn’t gotten to be together as much as they had wanted to. Still the love Dylan had for Shane was the same as his love for the rest of his siblings. He was broken to lose him so young. 

Dylan also has three protective sisters. Summer, Rainbow, and Desiree. All of whom would be like little mothers to Dylan. Trying to guide him to do the right things, correct him when needed, checking in on him, and loving him up, and offering a safe place if he needed it. 

Desiree is the youngest of siblings prior to Dylan and they were the closest in age and grew up together. Some of Desiree’s favourite memories were of them spending time together cooking in the kitchen, sitting around the fire pit with friends and family, or riding around together for hours being silly and cracking jokes. She will always cherish watching Dylan with her children as he was an awesome uncle to them. They had always been there for each other during difficult times. 

Rainbow was like a disciplinarian to her siblings as the oldest sister often is. Rainbow and Dylan being 16yrs apart and since they only lived together during the summer months when Rainbow would come to visit, it was easy to step into the role and help mom straighten up the kids when they got out of hand. I’m sure Dylan would have heard the saying, “I’m going to call Rainbow if you don’t listen” once or twice. Admittedly this phrase was probably used more on Eugene than anyone else but Dylan must have heard it too from time to time. Dylan was always on his best behaviour when big sister was around. either that or both the boys were nowhere to be seen. Rainbow was never a physical threat but she sure is good at long lectures on why their behaviours need to be addressed. Eugene once said, “how long is Rainbow coming to visit?” To which mom replied, “four days” and Eugene says, “that’s a long time to sit in the backyard”. Dylan was a good kid, he was smart and funny and he never really got these big sister lectures until these past couple of years of his life. Rainbow will always cherish her brother Dylan’s support when she would Sundance and he would be the fire keeper. This last Sundance was one of the hardest ones she had experienced and she had done this last one for him specifically. Sitting with her little brother under the stars with nothing but the sounds of nature and a crackling fire and then waking to the eagles chirping in the nearby trees will warm her heart forever. In her mind this is now where Dylan is. Safe among our ancestors in the most beautiful and sacred place there is. 

Dylan was also an awesome uncle to Jaida and Cobain. He was more like a best friend to Jaida since they were only 5yrs apart. They grew up playing together and then talked about partying together when they got older. Not your typical uncle niece relationship but special nonetheless. He was more of your typical uncle to Cobain, Kemsley, Jasmine and Tristen. All of whom loved him dearly. 

Summer remembers when Dylan was born. How happy and proud their grandfather was. A beautiful baby boy that was given the Olson last name.  “I always called him brother bear. He was just a lil cub so imagine our surprise when he grew into the big sabe he did. His heart was genuine and pure.  I’d often thank him for checking in on his uncle Rick, to which he’d let out his contagious laugh and shake off and say it’s no big deal sis. But it was, and it will always be.  He was a leader and an advocate for anyone who needed it.  That spirit will live on in the memories of everyone here who knew him. I will forever carry the honour of being a sister of his.”

Dylan filled out an “all about me” sheet when he was 19 yrs old and in school. It states the following. 

One interesting fact about me is…I drink a slurpee everyday. 

Memes make me happy 

If I could pick my dream job it would be sleeping for cash because I sleep when I’m broke. (Teacher writes, clever perspective)

Something I want to learn this year is something I don’t know yet

I’m afraid of not living a life worth living 

Something I’m really good at is Video Games

My favourite movie is anything Marvels, music group is Tech Nine, and my favourite food is pizza.

I find it funny when people mispronounce words. 

Dylan was someone special to everyone here. His love, kindness, generosity, compassion, and helping nature touched the lives of many and this includes his beloved pets his Cat Baby, cat Thriller and dogs Chloe and Oden. 

Dylan was also a protector to many but mostly he was always there watching over his mother Cecilia. Cecilia loves all of her children and has a special unique bond with each of them. Dylan was mom’s keeper. They took care of each other as best they could. He was the baby of our family and we were proud of him and always wanted the best for him. Creator called Dylan home and we may never understand why he had to go but we trust Creator will keep him safe on his new journey. 

If you wish to honour Dylan check in on his mother often after today, share the good memories of him, adopt a pet (he would have brought them all home if he could), help those in need, and share a smile can brighten someone’s day. Most importantly just be kind to one another. Thank you for your love and support during this time. Thank you for loving Dylan and sharing your pictures and memories with us. We will forever cherish the time we had with him.