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Leonard Winters

April 21, 1935 ~ January 5, 2021 (age 85)


April 21, 1935 to January 5, 2021

In his 86th year, tough guy Leonard Everett Winters died in Kingston of several recently discovered cancers, insisting until the end that he didn’t have any pain.  He leaves behind his loving and unbelievably supportive partner of 20-plus years, Karen Gordon, and his children, Kim and Andrew Pearson, and Chris and Karen Winters.  He was a proud Poppa of Joseph and Isaac Winters, and Ethan and Brynn Pearson. He will be missed by Eric and Hollie Gordon, their children Anna and Reed, Emily and Mark Baldwin, and their children Miles and Marley.   Len will be missed too by his brother-in-law and sister-in-law David and Betsy Allin, brother-in-law Ernie Pettigrew, sister-in-law Barb Winters, and many nieces and nephews across Canada.  Waiting for him in heaven are his wife of 32 years Teresa, mother-in-law Jean “Nanny” Duguid, all of his siblings: Red, Verlie, Spud, and Rusty, and his sister-in-law Evelyn.  Len was born in Parrsboro, Guysborough, Advocate Harbour, or Spencers Island, Nova Scotia, depending on when you asked him.  His mother died when he was 2 years old and his sister Verlie took over child-rearing duties.  Fiercely independent, he left elementary school very early in life and at 12 years old he was a fishmonger on the shores of the Bay of Fundy.  In the 1960’s he found work in Toronto.  Legend has it that on Sunday night he could make the drive from Nova Scotia to downtown Toronto in 12 hours to be at work on time Monday morning, and then would commute back home Friday night for whatever party was happening that weekend.  Len ultimately became a professional driver, based first out of Toronto, and then Napanee from 1976 on.  He drove a tractor trailer until his ‘retirement’ at 65, and then worked shuttling new vehicles around Ontario and Quebec until he was in his eighties.  Len had a gift for making a memorable first impression.  Strangers became friends quickly, usually thanks to a loud song (“Mamas, don’t let your babies grow up to be truckers”), a dance (he had more swivel in his hips than Elvis), a yodel, a crushing handshake (“Shake the hand that shook the world!”) or an unexpected wrestling match (one of his Toronto acquaintances was the great Whipper Billy Watson). Regrets?  He never mentioned any – our best guess is that his only regret is never winning the 6/49 jackpot with his best friend Ron.  Ours is that we didn’t get to enjoy him longer than we did.  Due to Covid19, Len’s funeral will be a very small family gathering, completely at odds with the number of people who were fans of his.  For that reason we will also honour him with an appropriate get together later, once it is safe to do so. As expressions of sympathy please be generous to the Lennox and Addington County General Hospital Foundation.  In the care of Hannah Funeral Home, in Napanee (613-354-3341).

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Private Services


L&A County General Hospital Foundation
8 Richmond Park Drive, Napanee ON K7R 2Z4

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