“For in that sleep of death, what dreams may come”
Shakespeare (Hamlet)

It is with great sadness that we announce the passing of Desmond Anthony Gilling on August 29, 2024 at the age of 74. He was surrounded by the love of his wife and best friend, Linda Gilling (née Belanger), and his three children whom he cherished, Randall Gilling, Kara Weatherall, and Lauren Facchini. He will be deeply missed by his family, including his sister Angela Gibson and his seven grandchildren, and his many dear friends. He joins his mother, Mary Gilling and sister, June Miles.

Desmond was born in Cricklewood, England on January 27, 1950 to Anthony Gilling and Mary O’Brien and had two older sisters, June and Angela. Desmond’s mother was born in Tralee, Ireland to Mamie and Patrick O’Brien. Patrick, known as “Granddad” to Desmond, was a multi-decorated WWI veteran and an excellent role model. He was impeccably dressed with a marvelous sense of humour. Desmond described him as, “wonderful, funny, charming, and gracious.” All traits that Desmond would go on to inherit himself.

Desmond’s mother moved to London in 1939. She worked in a munitions factory and later as a waitress. She met Anthony Gilling of Durham, England and married him in 1941. In 1956, when Desmond was six years old, they emigrated as a family from England to Canada by boat. The family settled in the East York area where Desmond attended St. Brigid’s Catholic Elementary School. Desmond became a bit of a novelty with the teachers there when they first heard his thick Cockney accent and saw his wide-eyed enthusiasm for his new life in Canada. When Desmond was nine, his father left on a trip back to England and never returned, leaving his mother to raise all three children on her own. They moved apartments often and lived modestly during these years. For Desmond, school was a reliable and safe place where he turned to books and friendships. He spoke fondly of the joys of bike riding around the neighbourhood, swimming at Monarch, playing sports in the school yard or make believe in the ravine, and exploring Toronto by streetcar on weekends. Desmond loved music and would often reminisce about dancing to Motown with his big sisters in the kitchen; one sister would have Desmond as their partner and the other would have the fridge door.

Desmond had a passion for academia and excelled in his studies from an early age. He was offered full scholarships to a variety of high schools and ultimately chose De La Salle private school where he was also a star basketball player. In 1965, Desmond transferred to Neil McNeil for his final two years of high school. During school breaks and on weekends, Desmond was a pool shark at The Alpine and the host of many house parties. Desmond’s skill of connecting and bringing people together began as a teen, long before the age of the internet and cell phones. If you ever wondered where everyone was going to be hanging out or what the plan was, you could just ask Desmond. It was also during these years that his love of cars took off, the first he ever owned being a Chrysler with the big fins. This would be one of the many cool cars Desmond would have in his lifetime.

Following graduation, Desmond “Des” attended Toronto Teacher’s College and became an elementary school teacher at Blessed Sacrament and then Our Lady of Fatima. While teaching, he attended night classes and summer school, gaining his Honours in English from the University of Toronto. Des was a great mentor to his students and a respected coach, taking his teams to provincial-level championships in volleyball and basketball.

In 1975, during his early years of teaching at Our Lady of Fatima, Des met the love of his life, “Miss Belanger”, a fellow teacher, whom he would write love letters and poems to, delivered by his students. After 5 years of dating, and many nights tearing up the dance floor, Des and Linda were engaged in 1980 in a log cabin on the French River on their way to PEI. They purchased their first home on Fraserton Cres later that year and then married on July 10th, 1981. This past summer they celebrated their 43rd wedding anniversary.

After dedicating 11 years to Our Lady of Fatima, Des moved on to high school where he taught English at Neil McNeil and later Pope John Paul II. While teaching high school English, he strived to make lessons engaging and interesting, sharing his love of poetry and literature with his students. Des was a social organizer and encouraged colleagues to join in on staff volleyball or take part in the Corporate Cup relay races. His enthusiasm was infectious. Des continued his passion for coaching, and was loved by both students and staff during his 17 years at Pope until his retirement.

In September of 1982, while teaching at Neil, Des became a father for the first time to his son, Randall. Des and Linda moved to their next home on Sloley Road where they would welcome daughters Kara and Lauren “Little Lo”. His role as a dad was his most precious responsibility and one that he thrived at despite little presence from his own. When asked recently what his favourite time in his life was, he replied, “When the kids were little”. Des was a hands-on dad, playing sports in the driveway or nearby school yard, building sandcastles at the beach and making snowmen in the backyard. Teaching them to dance on his feet in the living room and making up enchanting stories before tucking them into their bed at night were some of the ways he showed his love. Des was truly a natural.

Summers and weekends were spent enjoying “the farm”, their Victorian home north of Cobourg. In the city, Des and Linda would take the kids on bike rides around the Bluffs, across to Toronto Island, and through the Beach where, in 1991, they decided to move. At their new house on Silverbirch Ave, Des and Linda continued their love of hosting, gathering friends and neighbours for porch parties and barbecues. They also enjoyed rollerblading with friends along the boardwalk or venturing to Quigley’s (now Outrigger) to hear live music. Quigley’s and Busters were both sponsors of Des’s baseball teams. His years playing baseball and traveling with the team were full of fun, and many lasting friendships were made. Life for the “Gilling Gang” was never dull. Des and Linda loved adventures with the family to Sandbanks and PEI, and in particular, they looked forward to the annual Myrtle Beach road trip with friends over March Break. The twenty hour car ride was just as fondly reminisced about as the beach time. Life really is about the journey more than the destination.

Des enjoyed coaching all three of his own children in basketball and was a loyal fan to their many other sports competitions including cross-country and track and field races, or volleyball games. When they looked out into the crowd, they could always count on seeing their dad there, cheering them on. Editing school essays and giving casual history lessons at the dinner table were common practice at the Gilling household. As a dad, he was a balance of firm but fair, while being incredibly supportive of both school and social endeavors. He was also very loving and gentle, there to console, make you laugh, or to give wisdom when needed. Des held each of his children to high standards and instilled the importance of education, leading them to gain success in their own careers.

In 2001, Des retired from the TCDSB and was hired by Centennial College and Seneca to teach English and various writing courses. As an instructor, Des took on a double course load while embarking on entrepreneurial ventures such as his Golf, English Smart, and Theatre books to help finance his children’s studies at Queen’s University. His passion for grammar and writing took the form of a book he wrote and published called, “The Essential Handbook For Business Writing”. This book was used as a suggested resource for business students at Queen’s University and was used by Des for his many seminars and business writing workshops. This was something he enjoyed immensely and was very proud of.

Des was a man of many interests including art and literature, football and college basketball, history and film. He enjoyed going to movies with Linda and making bets with the family on which nominees would win the Oscar. His passion for culture and history made him a traveller with a special fondness for France, Spain, Italy, and Portugal. Des loved his Kingston Road community and he was a loyal patron at local establishments like The Lighthouse, Outrigger, and The Feathers Pub where he enjoyed having happy hour beers with his many neighbourhood friends.

Des was the life of the party and someone who brought people together. He was a lover of 50s and 60s music, a talented dancer, jokester, and gifted storyteller. His quick wit kept crowds entertained at countless weddings, retirements, birthdays, and memorials where he played the role of MC and organizer. His clever speeches and gentle roasting would have the whole room in stitches. To his close friends, he was someone who made you feel important. He always made an effort to make interesting conversation and dress nicely, regardless of how big or small the occasion. He was reliable, loyal, generous, and supportive. He was someone who would drop everything if you needed him.

Des was a treasured “Granddad” to his grandchildren: Miles, Blakely, Adelaide, Avery, Nathan, Charlotte, and Sloane. He loved to hold and “shhh” them to sleep, read them stories, and watch them adoringly as they played. Des was very proud watching his children, Randall, Kara and Lauren, become parents and they always hoped to be the kind of parent to their own that he was for them.

Over the past three years, Des endured a difficult health journey with much grace and resilience, with his wife Linda by his side through it all. After nearly two years of investigations and consults, Des was diagnosed with Interstitial Lung Disease, specifically Idiopathic Pulmonary Fibrosis. He kept this diagnosis private until a more clear treatment plan and outlook, and in January of 2024, he was diagnosed with Lung Cancer. This was a shocking turn of events for a long distance runner for over 30 years and someone who prided himself on his lung power. Des underwent chemotherapy treatments and with gratitude for the outpour of love and support he received, he began to compile his favourite poems and published a poetry book entitled, “A Collection of English Verse” to give in thanks to everyone who had been there for him. During the pandemic, Des carefully selected a poem a day for 365 days to send to Linda, and many of these poems were featured in his collection. He dedicated this book to his wife, children, friends and health care team.

On August 25, 2024, Des was admitted to Toronto General Hospital due to a fibrosis ‘flare up’ and CT scans confirmed that his cancer had spread - there was nothing they could do to treat him. He remained hopeful, brave, and witty until his final days. The day before he passed, Des expressed to his children that he felt lucky. He passed swiftly and peacefully, feeling the love of his family by his bedside. Des touched the lives of many and will be sorely missed. His sense of humour, dapper style, brilliant mind and kind soul will be forever etched in our memory.


Visitations will be on September 10th at 2-4pm and 6-8pm and on September 11th 10-11am followed by a funeral mass at 11-12pm all at Pine Hills Cemetery and Funeral Centre on Birchmount Road. There will be a reception after the mass and later a toast to Des at the Green Dragon on Kingston Road from 3-5pm.