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Massachusetts Insurance Legal News & Analysis

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.

Texas Agency Agrees To Pay $5 Million In Restitution and Costs

May 4, 2026 by Owen Gallagher

Adroit Health Group Barred in MA — $5M Settlement

A Texas-based health agency barred from Massachusetts and will pay $5M over three years for misleading consumers on health insurance coverage .

When Limited Market Access Meets Surplus Lines: An E&O Problem

April 27, 2026 by Owen Gallagher

Massachusetts surplus lines placement and E&O risk documentation

Massachusetts producers face E&O risk when surplus lines placements lack documented diligent effort. A breakdown of BR-7, §168, and defensible file practices.

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MA Division of Insurance Advertisements

Massachusetts Division of Insurance notice about Oakwood Insurance Company's license to transact life, accident, and health insurance.
Massachusetts Division of Insurance notice to Samsung Fire and Marine Insurance about license amendment for property and casualty insurance in the Commonwealth, dated July 31, 2026.
Formal regulatory notice dated July 31, 2026 from Massachusetts Division of Insurance to R.V.I. America Insurance Company about amending its foreign license to transact property and casualty insurance in the Commonwealth of Massachusetts.

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Career News

Quincy Mutual appointed Gerald F. Cox as president and chief executive officer following his tenure as CFO of Hiscox USA.

Quincy Mutual Announces New CEO

Salem Five Insurance Services appointed Gregory Grintchenko as senior vice president of insurance sales to support the agency's continued growth strategy.

Salem Five Insurance Services Expands Leadership Team with Addition of Gregory Grintchenko

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

Plymouth Rock Assurance Strengthens Leadership Team with Three Strategic Appointments 

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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

InSurOp-Ed: On This Day 30 Years Ago: What I've Learned

InSurOp-Ed: On This Day 30 Years Ago: What I’ve Learned

By Matt Masiello

Agency Checklists, MA Insurance News, Mass. Insurance, Lemonade, Lemonade Insurance Policy

InsurOp-Ed: Reverse Engineering – Making Lemons from Lemonade?

By Bill Wilson

InsurOp-Ed: InsurTech Conferences – Hear No Evil, Speak No Evil, See No Evil

By Bill Wilson

InsurOp-Ed: Transitioning to The Gallagher Way

By Tim Lodge

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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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