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Massachusetts Insurance Legal News & Analysis

Contractor Indicted For Comp Fraud On Sub Misreps

July 4, 2026 by Owen Gallagher

Construction site with workers on a roof, a clipboard labeled 'Workers’ Compensation Insurance Fraud' stamped FRAUD, a judge's gavel, and a book of Massachusetts General Laws.

A Milford contractor was indicted on workers’ comp. insurance fraud charges on allegations that roofing work was misclassified to reduce insurance premiums.

Massachusetts Bolstering Efforts to Prevent Wrong-Way Crashes

June 19, 2026 by State House News Service

Highway ramp with illuminated wrong way sign and safety technology used to prevent wrong-way driving crashes

Massachusetts expands wrong-way driving detection with sensors, signage, and alerts as fatalities rise and safety efforts intensify statewide.

Appeals Court Redefines “Contractual Relationship” Under Public Bond Statute

June 15, 2026 by Owen Gallagher

Massachusetts Appeals Court decision expanding third party beneficiary rights under Section 29 payment bond law

Mass. Appeals Court rules third-party beneficiary rights create a “contractual relationship,” avoiding Section 29’s 65-day bond notice requirement.

Guilty Plea in $6 Million Payroll Concealment Scheme

June 1, 2026 by Owen Gallagher

Federal prosecutors said a Lowell staffing agency owner concealed payroll and obtained workers' compensation coverage using false records.

The owner of a Lowell temporary staffing agency pleaded guilty in federal court to concealing more than $6 million in payroll and obtaining workers’ compensation coverage using false payroll records.

Court Rules: ‘Regardless of Whether’ In Exclusion Creates Ambiguity

May 4, 2026 by Owen Gallagher

Martha’s Vineyard aircraft propeller strike and CGL coverage dispute under Massachusetts law

A Massachusetts Federal court finds insurer must defend Vineyard hangar operator after $1.45M propeller damage claim.

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Career News

Gavin McPhail, Vice President and Chief Data Officer at Plymouth Rock Assurance.

Plymouth Rock Assurance Strengthens Leadership Team with Three Strategic Appointments 

G. Quinn Landers appointed Senior Vice President and Chief Claims Officer at The Andover Companies

The Andover Companies Appoints G. Quinn Landers Senior Vice President and Chief Claims Officer

Nick Fyntrilakis, President and CEO of the Massachusetts Association of Insurance Agents

Governor Healey Appoints Nick Fyntrilakis to Massachusetts Convention Center Authority Board

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MA Division of Insurance Advertisements

Official notice on Commonwealth of Massachusetts Division of Insurance letterhead dated July 1, 2026, regarding license amendment for OBI America Insurance Company at Plymouth, MN address for Accident and Health insurance in the Commonwealth.
Official notice from the Commonwealth of Massachusetts Division of Insurance about OBI National Insurance Company’s license amendment, dated July 1, 2026, with address block and filing instructions.
Official Massachusetts Division of Insurance notice to General Security National Insurance Company about amending its foreign license to transact property and casualty insurance, dated July 1, 2026.

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Interviews

From Nuptials, Tickets, and Taxes to Trusted Advisor: One Agency’s Unique Path to P&C Success

A Conversation with Evan Silverio, President & CEO of Silverio Insurance Group

Deland, Gibson Celebrates 125 Years: A Conversation with CEO Chip Gibson

The Fourth-Generation Family-Owned Agency is Based in Wellesley

Talking with Richard Welch: Growth and Innovation at Hospitality Mutual | Agency Checklists

Talking with Richard Welch: Growth and Innovation at Hospitality Mutual

Mr. Welch is CEO of Massachusetts-based Hospitality Insurance Group

Born and Bred in the Bay State: The Special Agent Story

Our Latest Agency Interview is with the Founder & President of Special Agent

A Conversation with Daniel C. Bridge – The 2023 Insurance Professional of the Year

Daniel Bridge is Board Chair, President, and CEO of Vermont Mutual Insurance Group

Making The Leap From Corporate to Entrepreneur: Nadeen Vella On Building NaVella Insurance From Scratch

Making The Leap From Corporate to Entrepreneur: Nadeen Vella On Building NaVella Insurance From Scratch

Our latest Agency Interview is with Nadeen Vella, the founder and owner of a virtual scratch independent agency.

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InsurOp-Eds

Business Interruption Insurance Massachusetts

InsurOp-Ed: Triple-I Thoughts on Business Interruption Litigation Filings

By Agency Checklists

Agency Checklists oped on atten

InsurOp-Ed: Observations And Insights For Insurance Agency Owners About IAOA’s INNOVAT19N

By David Siekman

InSurOp-Ed: When Policy Forms Don’t Do What You Think They Do

By Bill Wilson

Agency Checklists, MA Insurance News, Mass. Insurance News, Insurop-ed, Bill Wilson, Insurance Commentary from Bill Wilson

InsurOp-Ed: One Word

By Bill Wilson

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In Memoriam

Gordon Elliott Taylor, longtime owner of the Blackmer Insurance Agency in Shelburne, Massachusetts, who served the local insurance community for decades.

In Memoriam: Gordon Elliott Taylor

William R Berkley founder of W R Berkley Corporation and leader in commercial insurance industry

W. R. Berkley Corporation Announces the Passing of Its Founder and Executive Chairman, William R. Berkley

Michael R Quinn longtime leader of Allan M Walker Insurance Agency in Taunton Massachusetts

Taunton Insurance Leader Michael R. Quinn Dies at 70

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