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Jayson Tyrel Leary Obituary check_circle

With heavy hearts and profound sorrow, we share the news of the unexpected and untimely passing of Jayson Tyrel Leary. A pillar of strength, love, and laughter in the lives of those who knew him, Jayson’s legacy is one of warmth, generosity, and an indomitable spirit.

Jayson will be greatly missed by his wife Sherry, his son Brandon (Kaylee), his inseparable twin daughters Sadie and Alexis, and his loyal sidekick Sage. The depth of his loss is keenly felt by his parents Trudy and Jay, cherished sister Brenna (Deena), and caring sister Jodie (Randy). His nieces and nephews Ethan, Quinn, and Bode will miss having someone to whip them into shape at family gatherings.

Jayson knew everyone and if he didn’t, he quickly introduced himself. This skill, coupled with his unwavering partnership with his best friend and business associate Rick (Laura), saw them transform their brainchild, Oakpark Powerline, into an awe-inspiring enterprise in record time. He often expressed how proud he was to be able to provide his employees an opportunity to support their families.

Jayson cared deeply about others. It was not uncommon to come home and find out he had given away sports equipment to a friend’s child just getting started or lent out one of his many big boy toys. While he loved his toys (and grew a pretty impressive collection), he always said they were just things and could never replace his family or friends.

He was also a self-proclaimed “jack of all trades, master of them all”! Although most of us know he did more breaking than fixing, he somehow always made it work. He taught more lessons than most teachers and had a positive impact on nearly everyone around him—except for those few who might recall the mischief of southern Manitoba socials in the ’90s.

Full of life, laughter, charm, and a lot of BS (which was part of the charm)! His energy, ability to entertain, and use of the f-bomb more in one sentence than most people used in an entire day was epic! Jay had an immeasurable love for life, fun, family, and anything with a powerful motor! He always had our back whether we were right or wrong and was always there when we needed him.

Reflecting upon Jayson’s 44 impactful years on this planet, it’s as if we could compile the world’s longest book of memories, stories, and laughter—a testament to a life well-lived.

Jayson will continue his mischief with his deeply loved niece Addison, who he missed so much.

As we raise one last Grey Goose to Jay, let us remember him not with tears of parting, but with the smiles he brought to our lives, the love he showered upon us, and his unforgettable laugh that will forever echo in our hearts.

A Celebration of Life will be held on Thursday, August 31, 2023 at 2:00 p.m. at the Assiniboia Downs, 3975 Portage Ave, Winnipeg.

Rest in peace, dear Jayson.

Simply the best!

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