“And somewhere in the darkness,
“The Gambler” by Kenny Rogers
The gambler he broke even.
But in his final words,
I found an ace that I could keep.”
At the heart of our family history lies another remarkable story of resilience; when it wasn’t just a virtue but a way of life passed down through generations.
My maternal grandparents tied the knot on September 11, 1929, at the ages of 21 and 18, marking a significant date that would resonate 72 years later. However, unbeknownst to them, their union would also coincide with the onset of the Great Depression, triggered by the devastating stock market crash just a month after their wedding.
They had purchased a humble home located just down the street from my childhood home in The Coves, but as the economic turmoil swept through the nation, my grandparents, like countless other Ontarians, found themselves grappling with the weight of widespread hardship. While agriculture remained the cornerstone of Ontario’s economy, my grandparents didn’t farm and struggled to find employment within the city. The urban landscape was fraught with intense competition for scarce job opportunities, making an already difficult situation even more challenging for their family of ten.
Whiskey and whispers.
Raised during the era of prohibition and clandestine indulgence, my grandfather faced the turbulent currents of the Great Depression with the swagger of a seasoned gambler. Despite the repeal of prohibition and his lack of formal education (or as some might argue due to), he cleverly launched a “commercial transport enterprise” specializing in the local pickup, delivery, and distribution of goods—including the illicit sale and distribution of alcohol. An enigmatic figure cloaked in mystery and mischief, he frequently strayed beyond the boundaries of convention—and marriage—dabbling in creative revenue-generating activities that danced on the edge of legality and attracted unwelcome attention.
Although he was known to visit a brothel that later burned down and have inappropriate relations with his sister-in-law *shudder*, it was his role in a 1958 inquest following a tragic accident involving one of his company trucks that truly captured everyone’s attention.
While driving one of his trucks back to the yard in Strathroy after selling a load of horses, he was behind the wheel when the vehicle overturned, fatally crushing the passenger. Allegedly, the passenger, who had been asleep in the cab, abruptly awakened and either grabbed at the steering wheel or inadvertently collided with my grandfather, causing the truck to veer violently, throwing the passenger out the window and overturning. Despite extensive investigation by the police, the exact sequence of events remained elusive, and no charges were ultimately filed against my grandfather, who emerged from the incident unscathed. Nonetheless, the circumstances surrounding the accident sparked widespread speculation.
A legacy of resilience.
Amidst the backdrop of infidelity, scandal, and financial strain, my grandmother adeptly turned their adversities into opportunities. With her home situated on prime land—and eventual site for Elmwood Place Retirement Community, which was repurposed into a supportive housing complex to combat the homelessness crisis in 2024—she housed boarders to supplement her income. Concurrently, she invested in neighbouring real estate, all of which she eventually sold to her children. Furthermore, with pragmatism and perseverance, she established a thriving—and legitimate—dog breeding enterprise. While it’s bonkers to me that she sold her own home to her son James for a mere $5800 in 1974, her foresight paved a prosperous way forward for herself and her family.
Despite their unconventional and sometimes controversial—yet unforgettable—methods, my grandparents were remarkable individuals who epitomized the spirit of survival during an unforgiving time. My grandfather’s rebellious nature, although legendary within the family, was complemented by my grandmother’s unwavering strength, resourcefulness, and courage, which formed the basis for their family’s stability. Her resilience not only contributed to their entrepreneurial drive but also sparked the family legacy.