Playbook: Risk & Insurance

Rob Carpenter Tuesday, February 24, 2026

A handful of parent companies control America’s trucking insurance market

The seventh installment in FreightWaves’ investigation into America’s trucking insurance crisis reveals that the apparent diversity of the commercial truck insurance market is an illusion. Behind dozens of subsidiary names filing BMC-91s with FMCSA sit a small number of Fortune 500 holding companies. The concentration of risk is worse than anyone in the industry realizes.

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Rob Carpenter Friday, February 13, 2026

Trucking Risk Control Could Become the New Entrant Gate

For decades, insurance was the one thing you couldn’t fake your way past to start a trucking company. That’s no longer true. As instant-issue coverage and $300 authority fees make it easier than ever to place 80,000 pounds on public highways without verification, a scalable, pre-authority risk-control model could restore the gate the industry lost without adding a single federal employee to the payroll.

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Rob Carpenter Thursday, February 12, 2026

Inside the Shadow Market: 200,000+ Trucking Crashes Without Guaranty Fund Protection

My investigation found 76 Risk Retention Groups insure nearly 30,000 motor carriers linked to more than 6,300 fatal crashes, all without state guaranty fund protection for crash victims. The findings come as reports indicate that major insurers, including Chubb and AmTrust, are exiting the Chicago trucking market, funneling high-risk carriers into RRGs that have already incurred $199 million in unpaid losses and multiple insolvencies.

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Rob Carpenter Thursday, January 29, 2026

The $75,000 Bond and Truckers Left Holding The Bag

Nearly 88,000 trucking companies closed in 2023. Fraud losses topped $455 million in 2024. Carriers filing claims against $75,000 surety bonds are discovering that the pot’s already been split 50 ways. As the Supreme Court prepares to rule on whether brokers can be held liable for hiring bad carriers, it’s time to ask: who really bears the risk in freight, and is the system rigged against the people actually moving the loads?

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