Leonard James Gosling

Peacefully, at home, surrounded by family, Leonard James Gosling, (better known as Len “Boots” Gosling by his band mates and friends), found ‘Higher Ground’ on the morning of October 20th 2025 at 89 years young.

Len is survived and forever loved by his lifetime #1 fans, his wife of 60 years, Joanne Gosling, his Daughter Julie, who was there for him in his final moments, making sure he was comfortable and knowing that he is so loved, son, Ron (Amy) and his three granddaughters, Jennifer (late Tyler Mork), Stephanie and Joanne, as well as all of his great (and great-great) Grandchildren, Peyton, Paige, Max, Isabella, Emma, Katie, Allie, Benjamin and Ellie.

He was born in London Islington at Highgate Hill, the son of Kathleen and Richard Gosling. He also leaves behind his loving sister Josie in England, and his fun-loving nieces and nephews, Penny, Claire, Louise, Peter, and Paul, and his late sister Pat.

He and Joanne loved their annual trips to London to visit family and friends.

After doing his National Service in the RAF, Len went to Cordwainers school in Hackney, one of the major shoe-trade schools in the world. He then was working as a shoe designer with a London shoe manufacturer. He began playing guitar and was in a skiffle group. He then took up trombone and eventually joined a few jazz bands, he was playing with Ken Barton's Oriole Jazz Band when he was asked by a Montreal shoe firm to join them. That's when he emigrated to Canada in 1964.

He came to Montreal, Canada in 1964 and met his wife, Joanne four months later. Missing his music so much, an English fellow at Joanne’s work knew of a place with a Traditional Jazz Band. He and Joanne went to listen. He had his trombone with him and convinced them to let him sit in. Their trombone player was getting married and they asked him to play a gig up north the following month. He said he couldn’t as he was also getting married that day. Joanne said "sure you can!" They spent their wedding night in St-Sauveur at a jazz club. That led to him joining the Mountain City Jazz Band. Later on he joined the Al Peters Jazz Band, where they regularly played at the Cock N’ Bull Pub on St. Catherine Street.

Fourteen years later, when Greb offered him a job in Kitchener, Ontario, they decided to move. He loved trad jazz so much, he found a home for the genre at the infamous “Lancaster Hotel” on Lancaster Street, where he spearheaded a movement with the Sensation Jazz Band in the Waterloo Region, where jazz musicians from across Canada and the USA still migrate to, weekly to play.

He joined the Climax Jazz Band in 1981, and played Trombone alongside ‘Captain’ Chris Daniel’s, ‘Tricky’ Mick Lewis, ‘Happy’ Jack Vincken, ‘Bouncing’ Bob Erwig, Max Littlejohns, and ‘Awesome’ Jamie Aug, headlining jazz festivals with some of the most talented musicians across the world.

Len later founded the ‘Freeway’ Jazz Band packing the house and taking up residency at the Rex Hotel in Toronto for many years where his family often sat front row cheering him on, while he played the music he loved (and some he didn’t, like ‘Michigan Water Blues’ that he only played for his Granddaughter, Jen because it was her favourite).

When he finally decided the Toronto traffic became too much, he formed the “Boots Gosling Jazz Band” and played to a lively crowd at the KW Jazz Club in Kitchener with musicians who would sit in from all over, where he would eventually hang up his Trombone and Cornet to enjoy his life with his favourite K9 daughter, the late Cherry, who is now likely making him throw balls and give her treats, and his dog, Daisy and cat, Ozzy who will miss him very much.

Len’s sense of humour is unmatched and will carry on forever in the myriad of inside jokes he and his family have shared over the years.

He’ll be warm up where the sun continues to ‘Shine’ in his Quasi-coat.

It’s not goodbye, it’s until we see each other again. There’s a rainbow ‘round our shoulder, and it’s the love and joy that Len has given all of us.

Cremation has taken place. A Celebration of Life in Music for Len ‘Boots’ Gosling will be held at Smokeshow BBQ & Brew, 744 Mt. Pleasant Rd., Toronto, on Saturday, November 22, 2025 from 12 - 3 p.m. Musician friends are encouraged to bring their instruments as we open the stage to pay tribute to the late “Boots” Gosling in an afternoon of jazz. In lieu of flowers, memorial donations would be appreciated to the Kitchener Waterloo Humane Society.