About Us

We’re proud to say that we’ve been a family tradition since 1959, but it’s not only because so few roofing companies can make that claim. From the start, the company has been built upon a foundation of quality work and customer service and, despite the challenges that have come our way, the strength of that foundation has stood the test of time. It’s proof that what we do works.

The Early Years

In 1941, at the age of nine, Oscar helped his father build a roof on a three-story barn. It was his first roof … and his first fall. Afterward, his father often told the story of how Oscar got right back up on that roof to get the job done — not only was he a natural climber, he also never gave up.

Born with an entrepreneurial spirit, Oscar explored a few business opportunities in his early twenties but when he tried contracting, following in his older brother’s footsteps, he knew he’d found his calling and started Oscar’s Roofing in 1959.

Oscar’s expanded quickly in the first eight years and grew to include a crew of 72 men. The business was diversified into many lines of business (siding, insulation, soffits, facia, etc…) and covered a vast geographic area throughout Halton and Hamilton. It meant rapid growth, but it also became increasingly difficult to manage. The business was spreading too thin.

In the days before cell phones and answering machines, Oscar made himself available 24/7, with a business phone beside his bed. When a call came in at 2:00am, Oscar was there to answer it. He was rarely on a roof anymore; he had his hands full with managing staff and ensuring that the work flowed as efficiently as possible throughout the various lines.

With an urgent need to hire more help, Oscar took in three new men from Montreal. They set fire to his warehouse, stocked two stories high with materials for the year to come, and everything was destroyed. It was 1969 and time for Oscar to reflect and rebuild.

After the Fire: A New Name and a Fresh Focus

All that was left after the fire was an office on Queensway Drive. So, after taking some time to reflect, Oscar regrouped and got back on the roof with a fresh focus and a new name.

Before the fire, Oscar had sold the siding line of his business to his nephew Desi, who then started Desi’s Aluminum. In 1971, Oscar decided to take on the Desi’s name as well and Oscar’s Roofing became Desi’s Roofing. Both businesses would benefit when it came to cross-promotion, reputation and word of mouth.

The fire was destructive, but it also paved the way to reestablish focus. The business renewed its efforts in roofing and Oscar, together with his wife Jacquie, would do the work that he had first discovered at the age of nine.

By the end of the 70’s, the company had been renamed, refocused and relocated. Oscar and Jacquie moved their 466 Nelson Ave. location in 1977 and the company made its last move in early 2021 to 1-4391 Harvester Rd. 

A New Generation

The areas of Halton and Hamilton continued to experience exponential growth through the 1980’s and 90’s, presenting both a challenge and an opportunity for Desi’s to reposition itself to best serve its expanding customer base.

And so, in 2005, Oscar’s son Richard started Desi’s Roofing West to service customers in Hamilton and Stoney Creek.

As Oscar and Jacquie wind down and set their sights on retirement, Oscar’s son Ray, with his wife Tina, are taking over the reins at Desi’s Roofing.

And so the story continues. Over 50 years later, the family tradition is stronger than ever and with that, the highest level of quality work and customer service that people have learned to expect from the earliest days of our business.