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James St. James

Image by Nick Andréka


August 30, 1956 – May 22, 2024

It is with heavy hearts that we announce the passing of James Berry St. James on May 22, 2024 in Winnipeg, Manitoba at the age of 67. 

James is survived by his brother John (Sandra), daughter Sydney (Blaine), son Ryan, and grandson Jude.

James was born August 30th,1956 in Toronto, Ontario to John and Margaret (Berry) St. James. James grew up in Toronto alongside his older brother John who he always looked up to. Some of James’ fondest memories growing up were those he made at the all-boys Catholic high school Neil McNeil in East York and he remained close with other “Neilers” throughout his life. 

James loved sports and his knowledge of sports facts was encyclopedic! His favourite teams included the Winnipeg Jets, the Winnipeg Blue Bombers and above all else the Boston Red Sox. 

James was a born salesman. Starting back in the 70s when as a young man he worked at Florsheim Shoes in Toronto where he once privately served singer/actor Harry Belafonte, a story he loved to tell. He then went on to work in optical sales for many years followed by selling 50/50 tickets for the Toronto Maple Leafs/Blue Jays and then the Winnipeg Jets/Blue Bombers where he unsurprisingly loved being a part of the sporting events that brought him so much joy while making friends with everyone he met. He was proud to be the one to sell the winning 50/50 ticket to a young couple who used the money towards IVF treatments and welcomed a baby the following year. 

James loved to read and always enjoyed learning about a variety of different topics including history, sports, aviation, astronomy and world events. He loved to collect National Geographic magazines, sports memorabilia and antiques, and was often seen wearing his favourite sports team hats, jerseys and jackets (primarily the Red Sox!). He dreamt about travelling the world someday and was fascinated by planes and aviation, a passion that is shared by his 2.5 year old grandson Jude. If you gave James your flight number he would tell you all about the plane you would be on and track the flight from start to finish! 

James’ charismatic personality made him an easy person to become friends with and he is remembered by a huge number of friends and family across Canada who’s lives he has touched in many ways. James would have been the first to admit that he was most proud of his children Sydney and Ryan and his greatest joy was becoming “Pops” to his grandson Jude. 

James’ warmth towards others was instilled in his children so it is no surprise that both Sydney and Ryan went on to work in health care and the family asks that in lieu of flowers, contributions be sent to a local children's hospital or mental health organization.

The family encourages the sharing of stories, memories, and condolences by using the comment section on this tribute page.


Cremation & Life Celebrations

530 St. Mary Avenue - Winnipeg

204-421-5501 -

Memories, Stories and Condolences


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Joanne Benerowski

June 18, 2024 at 6:29 PM

James will be sorely missed by the CNE Foundation 50/50 team. We were looking forward to seeing him again this summer and were heartbroken to hear this sad news.


James was an absolute delight to work with. He made friends wherever he went and was easily our top seller. James was also willing to help new staff by passing along tips and suggestions.


We extend our most sincere condolences to James’ family and friends for your loss.


Rest in peace, James. You will be fondly remembered.

Colleen Okrainec

June 16, 2024 at 9:28 PM

With heavy heart 💔 tried to get a hold of my good friend last night as he did not show for his shift last night at the Goldeye’s. I received a call to say James St James passed away at his

apartment. I am mess last night and leaving work. James did sell the last 50/50 winner we had our last high five, our last hug, our last cheer and hug. Our chats went on long and me bugging him did you take your meds or where is your inhaler. We laugh. He was like a brother to me and I was annoying little short sister. I miss you until we meet again. ♥️♥️


I remember went he first joined the 50/50 crew who the heck was this tall guy with a huge heart and a voice that could be heard across the entire arena. To be a very kind warm and best friend you could ever come across.


You have touch so many people James & all the 50/50 crew will miss your smiling cheer at all the games. Blue Jays too


Look what I just found 🪙 thanks James miss you bud



Judy Lutz

June 16, 2024 at 4:45 PM

Rest in Peace James! John, Sydney, Ryan and Jude, I'm very sorry for the huge loss of James. James was such a nice man and I really enjoyed chatting with him. James was very modest, I told him several times that he was the best seller and he would make light of it. I'm going to miss his presence at the Arena.

Anita Spremo

June 15, 2024 at 1:36 PM

I first met James 5 years ago at MLSE. Every time he walked into the office, I would ask myself "who is this guy always chatting to everyone, always laughing and who could forget that big infectious smile!!

I said to myself "I want to get to know him better"!......and I did!

James was always so funny, kind, bighearted and just so nice to everyone 🤗

We drove up north together last summer in my car (just the two of us) and during that 2 -1/2 hour drive, I really got to know James on a more personal note and I will always be grateful for that car ride together.

May you rest in peace my friend and I will always remember how you made everyone feel. ❤️❤️❤️


Hava & David Salita

June 14, 2024 at 2:32 AM

My husband and I loved getting our 50/50s from him at the Jets games the last two years! Hugs and condolences to the family! May his memory be for a blessing.


June 12, 2024 at 7:32 AM

I had the pleasure of knowing and working with James for 5 years. With the Toronto Blue Jays and the Toronto Maple leafs. James was truly A treat to everyone who knew him. I will miss your endless stories, our battles at gate 5 for the most sales, but mostly your gentle smile, and big heart 💕

An Mai

June 9, 2024 at 10:26 PM

I had the pleasure of hiring James and introducing him to 50/50 back in 2018 at the Toronto Blue Jays. It was a privilege and honour to be able to work with James for three seasons. His energy and charisma for baseball and life was unmatched. I will never forget he sold his winning ticket to a young couple going through IVF treatment (Game 2 of the 2018 season), and the relationship he kept with that family many years later. This legacy will remain for many years to come, that I'm sure of.


I'll never forget him coming in early every shift with a coffee to discuss everything under the sun for hours just because he loved being in the stadium. To know him is to love him, and he won't ever be forgotten in our 50/50 family. I'm so glad I got the opportunity to know James. I know he's watching over the Ballpark every chance he gets now, even from above 🕊️


Rest in Peace James

Darrell Flett

June 9, 2024 at 2:46 PM

James lived in my basement suite when 1st moving back to Winnipeg. His laff could be herd through out the house. Always quick to lend a hand, a shoulder, a great listener. Always positive and always kind words. Rip 🙏 brother.

Larry Baillie

June 9, 2024 at 1:55 AM

I met James in February this year and in that short time he left a mark on me. Unfortunately I did not know we had so many similarities. I was a CAF member of the airforce, I grew up in Scarborough. Went to the first Blue Jays game in 1977.


i truly wished we were able to talk about so many similaritie. although I am grateful of that beautiful smile of James that would warm anyone's heart. You will be greatly missed by your 50/50 family. Also the smile you shared with many Winnipeg sport's fans.

Melanie R

June 9, 2024 at 1:40 AM

My deepest condolences go out to the family. In the short time I knew James he was a very special person to me and I enjoyed working with him selling 50/50 at Jets and Moose games. This coming hockey season and those to follow will not be the same without him saying to me "Go kill it kiddo" before we headed to our booths. You will always be remembered Rest In Peace my friend


June 8, 2024 at 10:17 PM

I didn't know you for very long, but we became fast friends. Rest in peace brother


Debbie Facey

June 8, 2024 at 11:37 AM

Words cannot express the sadness and sense of loss over James' sudden passing. I'm truly grateful that Jimmy was part of my story and the love never dies. May he sing with the angels and rest in eternal joy and peace. Until we meet again my friend! You will be missed ❤️

cousin Peggy J Vincent BC

June 8, 2024 at 2:27 AM

Well done Sydney, this is a good rep of JAMES,

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