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Born: Mar 24, 1948

Date of Passing: Jan 01, 2023

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March 24, 1948 - January 1, 2023

Passed on January 1, 2023, Gerald Winberg (Diamond or Berg), husband of Shirley; dad of Jesse and Lisa; papa of Ashton and Brendon (twins Aria and Amaya); brother of Joan and Peggy. He will be missed by Shirley's children, Sean and family and Kristin and by his large extended family.
Gerald was raised on Alexander Avenue in Weston, but lived most of his life in St. Vital. He worked over 38 years at Bishop Printing with his sister Nancy who passed in 2014.
With his outgoing personality Gerald made friends wherever he went. He had a great sense of humour, quick wit and could tell a good story. He enjoyed breakfast with his cousins and friends, family gatherings on Worthington and fishing in Bissett on the May long.
He was a big sports and music fan. He loved his Jets, the Stones and Willie. When younger he always rode a motorcycle. His favourite was his 68 Triumph he called his Sparkle Machine.
Gerald and Shirley travelled all across Canada, to the States, Mexico and Cuba. He loved their getaways to the Shooting Star and outings to South Beach.
Gerald was a good man. He loved his family. He loved his friends. He will be missed everyday. He will be remembered for his kindness, compassion and honesty and of course his beautiful blue eyes. About his life he said I met a lot of great people and I had a lot of good times. I wouldn't change a thing.
Respecting Gerald's wishes there will be no funeral. Please consider a donation to your favourite charity in his memory. A celebration of his life is planned for the summer.

Simple Cremation & Life Celebrations
204-421-5501 –

As published in Winnipeg Free Press on Jan 07, 2023

Condolences & Memories (15 entries)

  • Gerry and I were cousins, me about 10 years younger. Whenever we visited from Toronto, we would always walk to 1442 Alexander on Sunday to visit Aunt Peggy, Uncle George, Joan, Gerry, Peggy and Nancy. It was a small house but full of life. Gerry was COOL. He gave me rides on his motorcycle, painted his room dark-purple and was happy to amuse his younger cousins. As an 8-year old boy in the late sixties, I had heard of “hippies” and it seemed to me Gerry was one – long hair, jeans and called his father “the Old Man”. In the mid-1970’s he took me to a WHA Winnipeg Jets game to see Hull, Nilsson and Hedberg. He had season tickets and could walk to the old Winnipeg Arena from his home just off Ness (I always wondered if that was the reason he chose that location). I remember there were more fights in the stands than on the ice! Gerry had some ups and downs in life (Shirley was his best “up”), but he always persevered. It seemed to me that he never changed – he was caring, modest, loyal, relaxed about life, enjoyed a beer, loved his friends and, especially, loved his family. The evenings around the fire in Larry’s backyard will always be missing one person. - Posted by: Bruce Gardner (Cousin) on: Feb 12, 2023

  • My Dear uncle Jerry you will be missed immensely. But I have many fond memories spent with you and grandfather Bill Mason who passed many years ago I will take with me those memories of you and him together and the time I got to spend with you. Rest easy Uncle Jerry you will always be in my thoughts say hi to Ryan and grandpa I'm sure they were there to greet you ❤ - Posted by: Bobbi jo cady (Uncle) on: Jan 10, 2023

  • My sincere condolences to Shirley and family for your loss. I knew Gerry since elementary school. Upon meeting him, his genial personality and jovial sense of humour made Gerry instantly likeable; he was definetly a notable individual in the lives of those who were lucky enough to know him. Gerry will be sorely missed and warmly remembered. Rest easy, my friend. - Posted by: Jim Clemis (friend) on: Jan 10, 2023

  • I work for a physician who attended to Gerald. I have known him for many years and it was always a pleasure dealing with him and seeing his smiling face. He never complained and was such a gentle soul. My condolences to his family and friends, also to his lovely wife Shirley who I came to know as well. I will indeed miss him around the office. - Posted by: Lisa (Receptionist at doctor's office) on: Jan 10, 2023

  • Shirley, our Heartfelt condolences to you and you family. Yes, Jerry was a good man as well as a joyful one. These qualities always shone through. We always enjoyed bumping into you guys at South Beach and Shooting Star. We will raise a glass to him at the Golf Tournament. Godspeed Jerry. Ron & Barb. - Posted by: Ron and Barbara Coles (Friend) on: Jan 09, 2023

  • We’ve known Gerry for 30+ years and have so many fond memories of great times attending the Jets games. For all that knew this wonderful man it’s easy to say he was the most selfless, caring person that would give you the shirt off his back. Deeply missed. 💕 - Posted by: Michelle & Joe Cardwell (Friend ) on: Jan 08, 2023

  • My sincere condolences to Shirley and the family. I know Gerry will be missed by many. However I know he has reunited with his good friend Jim Murray in Heaven. They are probably reminiscing about the great lives they lived with no regrets. I can almost hear them laughing still. Take care Shirley. - Posted by: Karen murray (Friend) on: Jan 08, 2023

  • Dammit Gerry you left too soon!! All of Weston misses you. Like Chester said you were always there for pics at the WESTON BOYZ GOLF and to spread your humor at the Legion after. RIP buddy. I'm so sorry Shirley...your old neighbor-Dave - Posted by: Dave Gaeta (Friend) on: Jan 08, 2023

  • What a guy, Gerry was Weston's own Sports Illustrated Photographer. Always a happy guy, he will be missed. RIP Bud. - Posted by: Tom Hamilton (Friend) on: Jan 07, 2023

  • What can you say about Gerry except that he was a humble, friendly, hardworking father/grandfather/great-grandfather and genuine nice guy. I met Gerry on our first day at Weston school where we began our friendship. We spent countless hours playing various sports and activities, Gerry even joined the Boy Scouts much to the liking of his parents George and Peggy. Judy and I both loved Gerry and have many great memories of him. We especially enjoyed our trip with Gerry and Shirley to the Maritimes. Just like a Diamond, Gerry was one of a kind. R.I.P MY FRIEND - YOU ARE MISSED - Ralph & Judy Bell - Posted by: Gerald Thomas Winberg (Good Friend) on: Jan 07, 2023

  • I meet this wonderful man when I was just a youngster of 17 and he was 29. He would always say "What's your Mom's name Son" hahahaha. We were great friends then and 5 years later Charlie and I started our lives together and Gerry became my Brother in law. Never could I have thought to have a Best friend/Brother, to have so many laughs, so many crazy great times, so many beer with. One of the best was on one of our fishing trips, I was around 50 and he 62. We were both well intoxicated and I started tickling him for about 15 minutes until he almost pissed his pants. We had many a chuckle about that one. Anyway, everyone was so happy that Shirley and Gerry hooked up, which happen to be at my 40th birthday party. You will always be the love of his life Shirley. My Deepest Condolences. Love, Larry - Posted by: Larry Desjarlais (Friend, Brother in law) on: Jan 07, 2023

  • I’m so sorry for your loss of a beautiful man. Jerry was always a kind friend. RIP Jerry. You made everyone that knew you feel blessed. - Posted by: Meliny McClintock (Friend ) on: Jan 07, 2023

  • I have known Berg since grade school. He was a kind and warm hearted friend when we met and he stayed like that through out our friendship. He had a great sense of humor and a great laugh. We will miss him terribly. He and Shirley had many great times together and Gerry was so happy that they found each other. He was a great dad and cared about all his family and friends. I will miss our chats and coffee and stories. The Jets just lost one of their best fans..He is going to be missed by so many but never forgotten..He was a wonderful man. - Posted by: Grant Irvine and Maria Prymak-Irvine (friend) on: Jan 07, 2023

  • Gerry was one of the Weston Boyz golf gang … he, along with Tim Wright, was an official photographer, ie, picture taking guy at our annual golf tournament held at Players … growing up in Weston, we all hung out at the community centre where we played a variety of sports which for the most part kept us out of trouble … Gerry was one of the boys … will miss seeing him and having a chat with him at the golf gathering … sincere condolences to the family … RIP Gerry - Posted by: Jim Chester (Weston friend ) on: Jan 07, 2023


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