Florida Roofing Contractor Under Insurance Fraud Investigation Amid Nearly $1 Million in Claims

A Jacksonville roofing contractor known for community roof giveaway promotions is now the subject of a Florida Bureau of Insurance Fraud investigation following complaints from customers, employees, subcontractors, and suppliers who collectively allege they are owed nearly $1 million. Massey Contracting is facing multiple lawsuits over unpaid wages, unpaid material invoices, and roofing projects that were never completed after customers paid deposits.

According to court filings, former employees have obtained judgments for unpaid wages, while roofing supplier SRS Distribution alleges the company failed to pay approximately $927,000 for roofing materials purchased on credit. Customers also report paying deposits months ago for roof replacements that never began despite signed contracts and permits. The company’s owner attributes the financial collapse to a slower-than-expected 2025 hurricane season, saying anticipated storm-related roofing work never materialized and the company retained staffing levels it could no longer support.

For insurance claims professionals, the case highlights the financial risks associated with contractors that rapidly expand after catastrophe events. Adjusters frequently encounter roofing contractors working on insurance-funded repairs, making contractor financial stability an important consideration when projects remain unfinished or contractors become insolvent during repairs. Delays can leave policyholders with unrepaired property, create additional damage exposure, and complicate claim resolution…

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