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Unlicensed roofing ‘contractor’ in Hamilton, ON sentenced to ten days in jail

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Jason Dennis is "the worst case I've seen of an unlicensed contractor," said the head of building inspections for the city

Press Release from the City of Hamilton

HAMILTON, ON – October 26, 2017 – The City of Hamilton today announced the sentencing of Mr. Jason Dennis, an individual with a lengthy history of operating as an unlicenced roofing contractor in Hamilton.

At a sentence hearing on August 15, 2017, Mr. Dennis was given two years’ probation and ten days in jail for Breach of Probation – Building Repair Contractor without a licence as required by the City of Hamilton’s Business Licensing By-Law 07-170.

The probation order states that Mr. Dennis shall not to engage in any way, shape or form of employment in the roofing industry for two years. This was the eighth occasion that Mr. Dennis breached a previous probation order, committing the same violation.


The conviction stems from an incident with a Hamilton homeowner who hired Mr. Dennis in 2013. The roof was replaced; however, there were significant deficiencies and the homeowner was required to re-do the roof with a licenced contractor, effectively paying twice. In addition, Mr. Dennis failed to complete other work agreed to in the contract.

The homeowner filed a complaint with the City of Hamilton and a charge against Mr. Dennis was registered for failing to comply with a probation order of the Ontario Court of Justice. After nearly four years of investigative work by City staff, which included gathering statements and evidence from victims and associates, Mr. Dennis was convicted at a hearing in 2016.

Due to Mr. Dennis’ lengthy history of licensing offences with the City of Hamilton, City prosecutors requested 30 days in jail at the sentence hearing – the maximum that would have been permitted under the legislation.

Mr. Dennis operated under several different business names, including Top Quality Roofing & Renos; Grandview Roofing; Hamilton Regional Roofing; and Roofs R’ Us. Mr. Dennis himself has also used several aliases, including Jay Dawson, Jay Masters, Jay Gagnon and Jay Chambers.

Mr. Dennis also has a Provincial Offenses record dating back to 1993 and previous fraud charges with the Hamilton Police.


“The City’s dealings with Mr. Jason Dennis span almost ten years and point to the worst case I’ve seen of an unlicenced contractor. Mr. Dennis has defrauded at least 50 local homeowners out of thousands of dollars for work that was never performed. He capitalized through the home renovation business utilizing the mass market in Hamilton, which includes a large population of senior citizens.” – John Lane, Manager of Building Inspections, City of Hamilton

“I want to thank the victims who came forward in providing evidence to assist the City in its investigation of Mr. Dennis. I also want to extend my sincere thanks to the Ontario Ministry of Consumer Affairs and the Hamilton Police Service for also assisting City staff in their pursuit of Mr. Dennis to answer to very serious charges.” – Ed VanderWindt, Chief Building Official, City of Hamilton


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6 Comments » for Unlicensed roofing ‘contractor’ in Hamilton, ON sentenced to ten days in jail
  1. Robert says:

    Don’t you think he should have a longer period of lodging at the tax payers expense. Classic too little too late punishment. Based on his behaviour the state should seize all his assets, liquidate and disperse the funds to his victims.
    See how he would like it.

  2. Noel Murphy says:

    I am glad to see those pirates and charlatans brought to account. It is difficult enough for us legitimate professionals to operate our businesses and make an honest living without being smeared by the those rotten eggs.

  3. Roberta says:

    Ridiculous. Obviously he should have had to pay back to clients restitution, in the least.
    As a roofing contractor this is my clients worst nightmares. The cost of taking care of their homes is already high, without having to get it done twice.
    My question is why not hold him financially responsible also? Taking into consideration all the alias’s.

  4. Chris Langman says:

    As much as this is appalling behaviour to any decent professional, it should be understood that this person needs to make a living the same as anyone else. While his skill and ethical approach are not acceptable, it’s not as if he can resort to factory work any longer as we are outsourcing or automating these jobs more and more every day.
    The people Mr. Dennis has harmed in doing bad work are likely the same people who have chosen cheaply made foreign goods and hire the cheapest bid for any work they are unable or unwilling to do themselves.
    Mr. Dennis is likely a man with few options and until Canadians realize that a domestic economy is a fully integrated system, the Mr.Dennis’s of this country will continue burning people out of necessity.
    As much as I disagree with the approach, I must admire the persistence of the Mr. Dennis’s, who seem to be deterred by nothing.

  5. Joe says:

    Maybe this year 2018 if the Liberals get re elected, then they may will ask everyone in the Province of Ontario to be license, to eat, drink, breath, move around, to have sex, etc, wtf?

    Does a license teach anyone to do any work?

    Its a piece of paper which say in assumption one can do this or that work. Licenses are a system of control of a social services, called techno slavery, a fail system of trust, and irresponsible imposing treat, SSS self servitude slave. Worse than the Nazis on the thirties. The Liberal party in Ontario and maybe in the fed too, may come as treat to our way of life, if isn’t already here, under their masks.

    Hands on is what teach anyone to learn, to explore, the more experience the better one can perform. Just having a piece of paper on the wallet which says I am this or that and never had done it, is just pure bullshit. The reason the government wants people licensed its because its another form of taxing people for what they want to do as their careers.

  6. Shane Cooper says:

    Great story lol ten days is not enough!

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