A Norfolk County Grand Jury has indicted Quincy-based roofing company The Roof Kings, LLC, and its owner on charges stemming from an alleged multi-year scheme to evade workers’ compensation insurance premiums.
The June 25, 2026, indictments charge Craig Galligan and his company with four counts of workers’ compensation insurance fraud and one count each of larceny over $1,200. The Massachusetts Attorney General’s Office (AGO) alleges the scheme cost A.I.M. Mutual Insurance Companies, a Burlington-based insurer, approximately $584,962 in unpaid premiums.
The Alleged Premium Evasion Scheme
Workers’ compensation premiums turn largely on two inputs: total payroll and the classification of the work performed. Employers are obligated by statute to report both accurately, along with any uninsured subcontractors, so insurers can price the risk they’re actually taking on. Any uninsured subcontractor identified has their job classification and remuneration included in computing the workers’ compensation premium for the company that contracted with the subcontractor.
According to the AGO, Galligan told a different story during audits of policies issued between 2021 and 2024, representing that The Roof Kings carried little or no payroll and used only minimal uninsured labor. A joint investigation by the AGO and the Insurance Fraud Bureau of Massachusetts (IFB) later traced more than $1.5 million in payroll payments — run through the company’s bank accounts between 2018 and 2024 — that had never been disclosed to the insurer.
Why This Matters for Underwriters and Agents
This is one exposure that premium audits exist to catch. An uninsured subcontractor working on a roof is still a claim waiting to happen — the carrier is on the hook for the injury regardless of whether the premium reflected that risk. When a contractor misstates payroll or buries subcontractor labor, the insurer ends up carrying statutory exposure it was never paid to assume.
The AGO’s allegations here are essentially a case study in that gap: years of underreporting on exactly the exposures — undisclosed payroll, unreported subs — that the audit is designed to surface.
A Documented History of Safety Violations
The criminal indictments follow years of federal scrutiny of the company’s safety record. OSHA has cited The Roof Kings LLC repeatedly enough that its regional office has publicly labeled it a “serial violator,” including willful citations for exposing workers to fall hazards.
The company also has a history of noncompliance with its own settlement obligations: after The Roof Kings failed to honor a 2017 settlement agreement with OSHA, the U.S. Department of Labor sought — and in May 2021 obtained — a contempt finding from the U.S. Court of Appeals for the First Circuit, which appointed a special master to recommend corrective measures.
Statutory Penalties and Arraignment
Galligan and The Roof Kings are scheduled to be arraigned in Norfolk Superior Court on Friday, July 17, 2026.
Larceny over $1,200 under G.L. c. 266, § 30(1) carries a sentence of up to five years in state prison, or a fine of up to $25,000 combined with up to two years in jail. Workers’ compensation fraud under G.L. c. 152, § 14(3) carries up to five years in state prison, or six months to two-and-one-half years in jail, or a fine of $1,000 to $10,000 — with imprisonment and a fine also available in combination. As a corporate defendant, The Roof Kings, LLC faces the applicable fines; Galligan, as an individual, faces both fines and incarceration.
Section 14(3) also requires that, upon conviction, the court hold an evidentiary hearing to determine the insurer’s actual financial loss and order full restitution, reduced by any amount already recovered in a related administrative proceeding under subsection (2).
Prosecution and Investigation Team
The matter is being handled by Assistant Attorney General Kaelyn Hilliard and Criminal Investigator Dennis O’Connor of the AGO’s Insurance and Unemployment Fraud Division, with Victim Witness Advocate Lia Panetta of the AGO’s Victim Service Division, and assistance from investigators at the Insurance Fraud Bureau of Massachusetts.
