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Massachusetts Barred His Phony Insurance In 2006. Now Kevin Kolenda Has Pleaded Guilty To Wire Fraud

September 21, 2026 by Owen Gallagher

Kevin Kolenda prize insurance wire fraud case and Massachusetts insurance ban

Nearly 20 years after Massachusetts barred Kevin Kolenda from selling prize insurance without a license, the longtime operator of Hole-in-Won has pleaded guilty to federal wire fraud related to his prize insurance business.

The IFB: 106,707 Referrals Resulting in 4,823 Criminal Prosecutions

August 31, 2026 by Owen Gallagher

The Massachusetts IFB’s latest report reviews fraud trends, enforcement statistics, the Maxwell decision and key compliance lessons for insurers and agencies.

Grand Jury Indicts In $585K Workers’ Comp Fraud Scheme

July 13, 2026 by Owen Gallagher

Massachusetts prosecutors allege Roof Kings underreported payroll and uninsured subcontractor exposure to avoid workers' compensation insurance premiums.

Roof Kings owner Craig Galligan and his company were indicted on workers’ compensation fraud charges alleging nearly $585,000 in unpaid insurance premiums

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.

Physician Sentenced to Nearly Five Years Following Insurance Fraud Conviction

June 20, 2026 by Owen Gallagher

A Brookline physician receives 58 months in prison and $1.85M restitution after conviction for healthcare fraud, money laundering, and tax evasion.

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Career News

Chris Taylor, President and CEO of Plymouth Rock’s Independent Agency Group

Plymouth Rock Assurance Corporation names Chris Taylor President and Chief Executive Officer 

Ellen Mann, Vice President of Human Resources at Arbella Insurance Group

Arbella Insurance Group Promotes Ellen Mann to Vice President of Human Resources

After Sixty-Plus Years in “the Best Job in the World”, Warren Buffet Becomes Chairman Emeritus

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MA Division of Insurance Announcements

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

Agency Checklists, MA Insurance News, Mass. Insurance News

InsurOp-Ed: How to Explain Coinsurance to Clients

By Bill Wilson

The $1 Billion Blunder: How CrowdStrike’s Update Exposed Insurance Gaps

By Owen Gallagher

Agency Checklists, MA Insurance News, Mass. Insurance News, Safeco, Victor Pepin, how to become a Safeco agent in Massachusetts?

InsurOp-Ed – How to Guarantee a Bright Future for Your Independent Agency

By AC Editor

InsurOp-Ed: Horrible Policy Forms and Endorsements To Avoid or Be Wary Of

By Bill Wilson

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In Memoriam

In Memoriam: Stephen Joel Paris, 1938-2026

Jean E. Petersen worked more than 30 years at Kirby Insurance Agency in Whitman, Massachusetts.

In Memoriam: Jean E. Petersen, 1939-2026

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

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