JACKSONVILLE, Fla. – A Jacksonville roofing company once known for giving away free roofs is now under investigation by the State Bureau of Insurance Fraud, as customers, employees and subcontractors say they are owed a combined total of nearly $1 million.
Massey Contracting, a full-service roofing company that built its brand on community outreach and high-profile giveaway promotions, is now facing multiple lawsuits and a state fraud investigation.
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The company’s owner, Chase Massey, spoke with the News4JAX I-TEAM about the allegations and blamed a quiet season in the tropics last year for some of the issues.
Massey told the I-TEAM that his business model collapsed after no hurricanes struck Florida in 2025, leaving the company without the surge of storm-related roofing work it had counted on.
“Work slows down, you know, you try to keep everyone employed so they don’t go look for a new job, and everyone’s making really good money,” Massey said. “It comes to a halt quick, and I’d say I probably put myself in this position more than I’d like to think by not letting people go when I should have.”
Employees say they weren’t paid
Massey says the company employed more than 100 people at its peak. At least one of those employees has taken legal action over unpaid wages.
In a lawsuit filed by former sales manager Dean Richardson, a judge ruled in Richardson’s favor, ordering Massey to pay approximately $40,000 in unpaid wages. A subsequent attempt to garnish Massey’s wages was unsuccessful.
Court documents also reveal a zero balance in two of Massey’s savings accounts and just $1,409 in a third account.
Nearly $1M lawsuit from supplier
Court records show one of the nation’s largest roofing supply companies, SRS Distribution, is also suing Massey Contracting, alleging the company failed to pay nearly $927,000 for roofing materials purchased on credit.
The lawsuit also names Chase Massey personally, citing a personal guarantee he signed promising to repay the debt if the company could not.
Customers still waiting
Steve Otwell, a St. Augustine resident, says he is one of several Massey Contracting customers who paid a deposit for a new roof that was never completed. In his case, he paid $8,500 out of pocket and says he was never given a clear reason why the work was not done.
“The excuses range from parts to weather: ‘The cost of parts are going up; we’re going to work you out; some of my workers left,’” Otwell said. “It was just one excuse after another.”
Otwell says he signed his initial contract with Massey in September, anticipating the work would be completed before Christmas.
Free roofs, then fallout
Massey Contracting made headlines across Jacksonville in 2024 with a sweepstakes promotion featuring the company’s owners in a widely shared video.
“I’m Chase, and I’m Zach, and we’re with Massey Contractors, and we are giving away another free roof,” the promotional video states.
The roof giveaways themselves are not under scrutiny. However, the allegations of incomplete work, unpaid wages and supply costs are now the focus of a state investigation.
Owner promises resolution
Massey told the I-TEAM that he is aware of all the allegations and lawsuits and is hoping to rebuild both his business and the community’s trust.
He told News4JAX that his lawyers and attorneys for SRS Distribution have been in communication since the case was filed and that he expects all pending cases to be resolved within 30 to 45 days.
“Everyone should hear in the next 30 to 45 days — get the refunds if there’s work that’s not completed that we have contracts with,” Massey said. “Everything’s got permits on it, so it’s not like we just took people’s money and ran and didn’t do it the right way. I mean, everything’s permitted, and everyone has contracts and stuff like that. So if they do want a refund, they’re more than welcome. And we will refund them, that’s not an issue.”
For now, those are promises customers say they are still waiting to see fulfilled.