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ALEXANDER (ALEX) ALESHKA
Born: Mar 24, 1948
Date of Passing: Feb 16, 2026
Send Flowers to the Family Offer Condolences or MemoryALEXANDER (ALEX) ALESHKA
Alexander (Alex) Aleshka, born March 24, 1948, passed away on February 16, 2026, at the age of 77, after a short battle with prostate cancer.
Alex was born at sea, near Halifax, Nova Scotia. He then moved to Winnipeg as an infant, where he was raised by his parents, Maria and Peter Aleshka.
He will be lovingly remembered by his wife Irene Aleshka, daughter Carmyn Aleshka (Peter Davey), son Adam Aleshka (Rebecca McDermott), grandchildren, Madden, Miller and Adeline and step-grandchildren, Mira, Emily, Noah, Lachlan and Willow.
Alex was unique in every way, even his birth experience at sea exemplifies how he did things in his own, special way. He was the son of immigrants, who in 1948 were fleeing the uncertainty in war torn eastern Europe. Alex grew up feisty and strong willed and with an inherent gift to find a way to make a buck in any way possible. In the beginning this gift was used for survival, but eventually to provide his wife and two kids with a comfortable life funding high level education, world travel adventures, including a safari in Africa, two beautiful homes in Winnipeg and Palm Springs and a modern office in downtown Winnipeg.
Alex got into insurance sales shorty after university and quickly became one of the top producing insurance agents at one of Winnipeg’s largest insurance companies. Alex always liked to do things his own way and he quickly outgrew the limitations of a big company. He decided to establish his own independent firm and continued to sell life insurance until the last day of his life. Alex won countless awards and received many accolades selling insurance. He travelled the world based on his success selling life insurance.
Alex’s clients were like his extended family, and they appreciated him exactly as he was. He would have stacks of paper and client files all around. He would show up to meetings with his baseball cap on backwards and wearing pyjama pants. He never bothered to learn how to turn on a computer or send a text. He mastered the art of a phone call, the art of in person meetings and the art of sales. For five years, the years he claimed were the best in his career, he worked alongside his son and daughter and taught them the ins and the outs of the insurance business. He also worked alongside his wife Irene who operated a very successful mutual fund business for over 20 years while he ran his insurance practice. They were a dynamite team. Irene was truly his rock and confidant, doing it all with incredible patience, kindness and wisdom.
Alex didn’t have many hobbies outside of work and managing his insurance clients, except for sports betting. It was a major hobby of his up until the week before he passed. For Super Bowl LX he had at least 10 bets going to family and friends and was excited to see how his last set of bets turned out - of course he came up the winner as always (even though he had bets on both teams).
Alex spent his last four weeks with the people he loved, making sure the details of his succession plan got done as he desired. May he rest in peace.
A private funeral service will be held by the family and a celebration of Alex’s life will be held at a future date. In lieu of flowers, family asks that a donation can be made in memory of Alex to KIDTHINK Children’s Mental Health Centre, 407 Graham Ave., 2nd Floor, Winnipeg, MB R3C 0L3 www.Kidthink.ca
As published in Winnipeg Free Press on Feb 21, 2026
Condolences & Memories (1 entries)
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Alex and I met in the early 1970s as we had both joined the insurance industry at the same time. He was definitely a unique character and we had many visits together in the early years in the business. He had a tremendous passion for the industry and a lot of families and businesses were looked after because of his desire to sell life insurance. He had a unique style, but a good heart. The industry was very fortunate to have people like him – – !!! 77 is far too young. A good man. - Posted by: George Sigurdson (Business friends) on: Feb 21, 2026
