Insurers Judged By The Trucking “Company” They Keep

NTSB Photo From the Triton VA Bus Crash in 2024

Rob Carpenter

Sun, February 22, 2026 at 8:12 PM GMT+9 23 min read

When a truck kills someone on an American highway, we ask the obvious questions. Who was driving? Who was the carrier? Was the driver fatigued, impaired, distracted, or untrained? Was the vehicle maintained? Were the hours-of-service records real?

There’s a question almost nobody asks: Who insured them?

That question tells you more about what went wrong and what will keep going wrong than almost anything else in the crash file. Insurance is supposed to be the gatekeeper. It’s supposed to be the one checkpoint in this entire system that requires someone with actual underwriting authority, risk control expertise, and capital at stake to look at a motor carrier and say: yes, I’m willing to put my company’s money behind this operation.

So let’s ask the question across the crashes that have defined the last year of American trucking.

Indiana: Four Amish Men, February 3, 2026

Henry Eicher, 50. His sons Menno, 25, and Paul, 19. Family friend Simon Girod, 23. Killed on State Road 67 in Jay County when a Freightliner driven by Bekzhan Beishekeev failed to stop for slowed traffic. The carrier was AJ Partners LLC, part of the Sam Express chameleon network, operating roughly 800 trucks across more than 20 interconnected Illinois-based authorities that share equipment, drivers, and officers.

AJ Partners was insured through Ace Property and Casualty Insurance Company.

Tutash Express: 57 crashes, over 1,800 inspections, driver OOS rates exceeding the national average; was insured through State National Specialty.

Sam Express, the mother of the network, carried Artisan and Truckers Casualty Company, and, before that, Accredited Specialty and Texas Insurance.

KG Line Group, 310 trucks claimed from a residential home in Streamwood, Illinois, has had an insurance descent you can watch in real time: Artisan and Truckers Casualty → Sutton National → AmTrust Insurance Company (until January 21, 2026) → Universal Casualty Risk Retention Group (effective January 21, 2026). Universal Casualty is an Oklahoma-chartered RRG that markets itself as an insurer for auto dealers and servicers. Now it’s covering a carrier connected to a chameleon network with nearly 100 crashes.

Texas: Five Killed, June 28, 2025

Five people died on I-20 near Terrell, Texas, when a Hope Trans LLC semi hauling U.S. mail slammed into stopped traffic. The driver, Alexis Osmani Gonzalez-Companioni, admitted he fell asleep at the wheel. He was driving solo on a route that, under USPS policy, required team drivers. The truck’s cab card was falsified. A company official was indicted. Former drivers described a culture of falsified logs, backdated shipping documents, and coded language; “coffee” meant they needed more illegal drive time.

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Hope Trans was insured through State National Specialty Insurance Company, the same insurer that covered Tutash Express in the Indiana chameleon network. After the Terrell crash, public pressure mounted, and the policy was eventually cancelled in October 2025. Hope Trans is itself a documented chameleon operation: investigators traced 45 trucks moving through Kardan Trucking (shut down after two fatal crashes in Iowa) to Bee Zone Logistics to Hope Trans. Hope Trans has reappeared under a different USDOT number in Forney, Texas, currently insured through Benchmark Insurance Company.

Florida: Three Killed, August 12, 2025

Three people were killed on the Florida Turnpike in St. Lucie County when White Hawk Carriers driver Harjinder Singh made an illegal U-turn at an official-use-only median opening. A minivan slammed into the side of his trailer at highway speed in an underride crash. Singh failed an English Language Proficiency assessment after the crash, correctly answering only two of 12 verbal questions and identifying only one of 4 highway signs. He faces three counts of vehicular homicide.

White Hawk was insured through Great West Casualty, one of the most reputable trucking insurers in the industry. But here’s the tell: at the time of the crash, White Hawk’s policy was already pending cancellation. Great West had already trended this risk profile and determined they were not a good fit. The renewal date was August 19, one week after the crash. Great West decided not to renew.

Before Great West, White Hawk was insured through American Transportation Group, a Risk Retention Group. Before that, National Wilshire and other non-standard markets. This is the descent. A carrier comes out of an RRG, somehow gets into a top-tier insurer like Great West, Great West figures it out, and is already on its way to non-renewing it when the crash happens. The insurance history told the story before the crash did.

White Hawk also had documented chameleon connections; its principal was linked to White Star Trucking out of Modesto, which closed in 2013. FMCSA revoked White Hawk’s operating authority after the crash.

Virginia: Ashley Chapman, August 24, 2023

You don’t have to look at a massive chameleon network to see how this plays out. You can see it in a municipal waste hauler right here in Virginia.

Lucky Dog Industries was a waste hauling operation in the Washington metropolitan area. Poorly run. High crash frequency. On August 24, 2023, one of their trucks was traveling southbound on Route 17 in Gloucester County and failed to slow down for stopped traffic. The tractor-trailer slammed into the back of a Chevrolet Beretta. Ashley Chapman, 25 years old, was killed.

Lucky Dog had been switching insurance nearly every year. Each year, when their agent went to market them for renewal, the insurer pool got smaller. Their FMCSA performance history was catching up with them. They burned through the standard markets. They burned through the subprime markets. Eventually, nobody would write them. They were still operating. Still putting 80,000-pound trucks on the highway next to a 25-year-old woman in a Beretta on a Thursday afternoon.

The Pattern

Indiana: Ace, State National Specialty, Artisan and Truckers, an auto-dealer RRG.

Texas: State National Specialty. Then Benchmark.

Florida: An RRG, then Great West, pending cancellation.

Virginia: A carrier cycling through insurers annually until nobody was left.

You can look at each of these crashes in isolation and find the proximate cause: a driver who didn’t stop, a driver who fell asleep, a driver who made an illegal U-turn, a driver who failed to slow down. Behind every one of those drivers is a carrier. Behind every one of those carriers is an insurer who said yes. Or an insurer who was already saying no but hadn’t finished the paperwork yet. Or an insurer that never should have been in the trucking business in the first place.

The insurance history is the tell. It has always been the tell. We just never organized the data in a way that made the pattern visible at scale.

The Flat Line

If you’ve been listening to the political conversation about trucking safety, you’ve heard a specific narrative: that the surge in new-entrant carriers, non-domiciled CDL holders, and barrier-free licensing has made American highways deadlier than ever. I’ve wanted to make that argument myself. For years, I’ve looked for the fatality data to support it.

It doesn’t.

According to IIHS analysis of FARS data, large truck crash fatalities have hovered in roughly the same range for 35 years. In 1990, 5,174 people died in crashes involving large trucks. In 2000, it was 5,173. By 2023, it was 4,354. There was a recession-driven dip to 3,147 in 2009, less freight moving, fewer trucks, fewer deaths, and a post-COVID spike to 4,765 in 2022. The trendline has been essentially flat: 5,000, plus or minus 500, for three and a half decades.

Consider what changed between 1990 and 2023. Truck miles traveled more than doubled, from 146 billion to 330 billion. Active motor carriers exploded from roughly 300,000 to over 2 million. The industry mandated ABS, electronic stability control, and ELDs. Collision mitigation, lane departure warnings, and adaptive cruise control became increasingly standard. On the passenger vehicle side, the improvements were even more dramatic: airbags, side curtain protection, automatic emergency braking, and advanced crumple zones. Seat belt usage climbed from roughly 60% to over 92%. Trauma care improved significantly.

The IIHS data shows exactly what all of that investment accomplished. The passenger vehicle occupant fatality rate per 100 million truck miles traveled dropped from 2.59 in 1990 to 0.86 in 2023. A 67% decline in the rate. If the 1990 rate had held steady with 2023 truck miles, we’d be looking at approximately 8,500 passenger vehicle occupant deaths per year instead of 2,827.

The safety technology worked. It saved roughly 5,700 lives per year in passenger vehicle occupants alone. The absolute number barely moved. Something absorbed all of those gains.

We tripled the number of carriers. We doubled the truck miles. We lowered every barrier to entry: authority, CDL issuance, and insurance. We created an instant-issue insurance market. We allowed RRGs with no guaranty fund backstop to finance risk profiles that the traditional market rejected. We turned the CDL from a professional credential into a consumer product.

Every airbag, every ABS module, every ELD, every lane departure camera, every dollar spent on road design and median barriers and rumble strips,all of it has done nothing more than hold the line. Thirty-five years and hundreds of billions of dollars in safety engineering just to break even at 5,000 dead.

That flat line is not evidence that the system is working. It’s evidence that the system is consuming its own safety gains as fast as it produces them. The political debate wants to make this about demographics. It’s not. It’s about systems. It’s about the structural failure of every checkpoint that was supposed to separate the operators who belong on the highway from the ones who don’t. Of all those checkpoints, authority issuance, CDL testing, FMCSA enforcement, and new-entrant audits, insurance was supposed to be the final one. The one with real money on the line. The one that couldn’t be faked.

Seat at the Table

I might be a writer and a journalist, but I didn’t just pick up a hobby in the industry; I live in the trucking industry every day and have for decades, so here’s some first-person pro data for the masses. I speak at dozens of insurance events, risk control conferences, and board of directors meetings every year. I work for hundreds of insurers and third-party administrators around the country, assessing fleet risk, particularly for captive and group captive insurance programs. These are the organizations at the top of the insurance hierarchy. They have risk control dollars built into the fabric of their policies. They pay professionals like me to walk into a fleet, assess the operation from the ground up, and tell them whether the carrier belongs in their program.

Most consultants in this space focus on compliance. I focus on defensibility. I build programs around the loopholes, the gaps between what’s technically compliant and what will actually survive a plaintiff’s discovery process, a deposition, or a courtroom. I think in terms of reptilian theory, because that’s what the plaintiff’s bar thinks in terms of. If you don’t understand how a trial lawyer will weaponize your compliance failures, you don’t understand your risk profile.

I’ve held a CDL. I’ve dispatched freight. I’ve brokered loads. I’ve owned and operated fleets. I’ve worked in private equity, overseeing transportation companies. I’ve performed crash reconstruction and served as an expert witness in highway accident litigation. Risk in trucking doesn’t live in one department. It lives everywhere: in how a driver is recruited, how a truck is maintained, how a dispatcher manages hours, how an owner responds to a crash, how a broker vets a carrier, how an insurer prices a policy. If you can only see one piece of that chain, you can’t assess the whole risk model.

What we see, from inside the boardrooms of the best-run insurance programs in this country, is an industry increasingly alarmed at what’s happening at the bottom of the market. The bottom doesn’t just affect the carriers and the victims. It drives up reinsurance costs. It fuels the nuclear verdict cycle. It poisons the actuarial data. It makes it harder for well-run carriers to find affordable coverage because the market can’t distinguish between them and the carriers that should never have been insured in the first place.

Why I As a Person, Not a Journalist, Push So Hard

People ask me why I push so hard on this. Why don’t I just consult quietly, collect the fees, and move on? Why do I write these articles? Why I built these tools. Why am I on the phone with reporters and regulators and plaintiffs’ attorneys when I could be doing something easier with my time?

The answer isn’t professional. It’s personal.

I’ve worked on crashes like Ashley Chapman’s. I’ve reviewed the files. I’ve looked at the driver qualification records that should have prevented the crash. I’ve looked at the maintenance records that should have kept the truck off the road. I’ve looked at the insurer that should have non-renewed the carrier two years earlier. Every time I work one of these cases, I think the same thing: what if that were my daughter?

Nothing in this world devastates me. I’ve been through things that would have broken most people. I’d be lost without her. The thought that one of these carriers, a carrier with falsified records, insured by an RRG that has no business writing trucking policies, a carrier that’s already burned through every legitimate insurer in the country, could put a truck next to her on the highway today and kill her? That’s not a click-worthy headline to me. That’s a reason to find a solution.

My brother died at 28. My sister died at 38. My father died in a crash at 43. I’m 44 years old and the oldest and the only remaining member of my immediate family. That’s an insane sentence to write. Every one of those losses involved something that could have been prevented. Not by better luck. By better systems. By someone somewhere in the chain doing their job, raising the flag, and saying no.

That’s what insurance is supposed to do. That’s what underwriting is supposed to do. That’s what a risk control assessment is supposed to do. It’s supposed to be the moment in the process when someone with authority and accountability assesses the risk and decides whether it belongs on the road. When that system works, people go home to their families. When it doesn’t, someone’s daughter, someone’s brother, someone’s father doesn’t come home.

I don’t push hard because it’s good for business. I push hard because I know what it feels like to be the family that gets the call. I refuse to look at these crashes, at Ashley Chapman, at Henry and Menno and Paul and Simon, at the five people in Terrell, at the three people on the Turnpike, and treat them as statistics. They were someone’s people. The system that was supposed to protect them failed.

A Quick Primer: RPGs, RRGs, and Consortiums

A Risk Purchasing Group is a buying consortium. Think of it like a drug testing pool. A handful of three-truck carriers band together through an RPG, and now they’re a book of business worth competing for. The RPG holds zero risk. If it dissolves tomorrow, the members still have their individual policies with the actual licensed insurer.

A Risk Retention Group is the insurer. It’s a member-owned insurance company authorized under the Federal Liability Risk Retention Act of 1986. The members pool their resources and self-insure. The RRG collects premiums, holds reserves, and pays claims. It sits in the same seat as Great West or Progressive. Except it operates under completely different rules.

RRGs are federally prohibited from participating in state insurance guaranty funds. Under 15 U.S.C. § 3902(a)(2), if an RRG goes insolvent, crash victims have no backstop. We saw this with Spirit Commercial Auto RRG: a crash victim named Brian Richardson had a judgment, a settlement, and nothing. We saw it with Global Hawk RRG: collapsed in Vermont, 1,008 trucks effectively uninsured, the president embezzled $19 million.

RRGs are primarily regulated by their domicile state, not by the states where the actual risk operates. Vermont alone houses 85 licensed RRGs that wrote $2.92 billion in gross premiums in 2023. That’s the regulatory arbitrage play.

The RRG structure itself is not the problem. OOIDA’s RRG has served owner-operators for nearly 25 years. ATTIC RRG insures large, safety-minded fleets operating over 7,000 trucks. The problem is when the structure becomes the last refuge for carriers that no traditional insurer will touch.

The Insurance Descent

Insurance in trucking is a hierarchy, and where a carrier lands tells you almost everything about how they run their operation.

A clean carrier starts in a standard or preferred market. Multiple insurers want the business. Then the performance history accumulates. Crashes. Violations. An out-of-service rate that climbs. Each renewal cycle, the insurer pool shrinks. Standard markets disappear. Subprime kicks in: $25,000, $30,000 or more per truck per year. Eventually, even the subprime insurers won’t renew. That’s when a carrier ends up at the very bottom: instant-issue policies, non-standard markets, and certain RRGs willing to finance risk profiles that nobody else in the industry will touch.

Once you’re at the bottom of the insurance barrel, you’re at the bottom of the freight barrel. The best shippers and brokers won’t work with you. The brokers hauling dock-bumper freight, commodities of little value, U.S. mail, and garbage are looking for the cheapest possible carrier. The insurance descent and the freight descent are the same descent. They feed each other.

Why Aren’t You in a Captive?

On the opposite end sits the group captive model. A member-owned program where carriers with exceptional risk profiles pool together. If everyone performs well, low crash frequency, low severity, and strong compliance, everybody gets money back. It doesn’t cost you money to be in a captive. You actually get money back as a member-owner. Nobody wants trash carriers in their group because the more risk a carrier brings, the more risk everyone absorbs.

The underwriting process is rigorous: someone with real risk-control expertise is looking at your operation, driver files, maintenance records, and crash history, and making a decision about whether you belong. That’s what those risk control dollars pay for. That’s why these organizations bring in consultants like me.

So when I walk into a large carrier for the first time, the first question I ask is: why aren’t you in a group captive?

I have a carrier down in Louisiana right now. Five thousand trucks across the country. A legacy operation. They have a million-dollar deductible on their insurance policy for every crash. They’re insured with Travelers. Travelers is a great insurance company; I’m not knocking them. But the only reason a carrier like that isn’t in a group captive is one of three things. Either they’ve been lucky to stay this big with a bad risk profile. Or a captive group has looked at their history and won’t accept them. Or, and this is more common than people think, they just don’t know captives exist.

Many large trucking companies are unaware that group captives are an option. They’ve been paying subprime or standard rates their entire existence because nobody told them there was a market specifically designed for legacy carriers with good risk profiles. If you have 5,000 trucks and you’ve been in business for 70 years, you should be asking: Why do I have a million-dollar deductible? Why am I not in the market designed for people like me?

The insurance placement is the tell. It’s always the tell.

Insurance Was Our Jet

Here’s the way I’ve been explaining this for years:

Insurance was our jet.

You can pay the $300 fee to get your operating authority. You can get a free DOT number. You can rent a Penske truck for $1,000 a month. You can fake your driver qualification files. You can get access to unlimited freight for less than $1,200 in startup costs. You can fake all of that.

Think about it like the influencer economy. Influencers can rent a Bentley from Enterprise Exotics. They can book a $10 million house from Airbnb for a night and take pictures. One thing they can never, ever fake is the jet. You can’t rent a Gulfstream for a photo shoot. The jet is real, or it isn’t.

Insurance used to be our jet. The one thing in the entire new-entrant process that required someone with actual capital at stake to look at your operation and say yes. The gate.

We’ve dismantled that gate. We’ve created instant-issue policies where you get a quote in minutes, a policy in hours, and nothing more than a self-attested application. No inspection. No driver file review. No verification that the three trucks you declared are actually the thirty trucks you’re running. GEICO entered the commercial trucking market in 2025. Progressive has been there for years. They’ve turned commercial motor vehicle insurance into a consumer product.

Below them sits the subprime tier: surplus lines insurers, non-standard markets, companies willing to write policies for operations nobody else will touch. Below that, certain RRGs and marine insurance products that I’m increasingly seeing on FMCSA filings, products that deserve their own investigation, because marine insurance coverage for a trucking operation raises questions about whether the policy structure actually provides the protection a traditional commercial auto liability policy would.

Scoring the Company They Keep

This is exactly why we built the Insurance Intelligence module on theteaintel.com.

For 25 years, traveling around the country assessing fleets for insurance companies, I realized that it wasn’t the fleet I should be looking at. It was the insurance company. The captive programs are serious about who they let in. If an underwriter lets a bad carrier into the captive, every member shares in that risk. Collective accountability. Shared skin in the game. The way the rest of the market works, everyone in society shares the risk of whoever the insurer decides to put on the road.

So we did something nobody had done before. We took every motor carrier in the federal FMCSA census data. We took every insurance company paired with those carriers. We reviewed historical compliance profiles, crashes, violations, out-of-service rates, and revocations for each carrier covered by each insurer. We ranked the insurers based on the company they keep.

We assigned a 0–100 composite risk score to every carrier using five FMCSA-linked indicators: crash history, fatal crash history, out-of-service rates, total violations, and prior revocations. Then we aggregated those scores by insurer.

Jason Miller at the University of Michigan saw the value immediately. His words: “No one has ever written about it.”

Look at Omnia Risk Retention Group. Fourteen carriers are insured under their flag. Average carrier risk score: 47. Those 14 carriers have collectively been involved in over 6,000 crashes, 200 fatalities, and 3,580 injuries. Fourteen carriers. Six thousand crashes. You can see all of this aggregated in the insurance lookup tools on theteaintel.com.

The scoring methodology is something we’ve been sharing openly. If you run a platform, research program, or newsroom and want this data, reach out. This data should be everywhere. The more visibility there is, the harder it becomes for the bottom of this market to operate in the dark.

The $750,000 Question

The federal minimum liability for motor carriers has been $750,000 since 1980. Adjusted for medical cost inflation, that’s roughly $4.9 million in today’s dollars. Purchasing power has eroded by approximately 85% over the past 4 decades. Nuclear verdicts exceeding $10 million have become routine, with median payouts reportedly doubling from $23 million to $44 million in recent years.

Multiple legislative attempts to raise the minimum have failed, largely due to opposition from OOIDA, ATA, and a coalition of more than 60 trucking trade associations. The industry’s counter-argument: approximately 98% of cases settle within current limits.

Minimums aren’t designed for the 98%. They’re designed for the crash that kills four Amish men on a Tuesday afternoon. For the carrier with 91 crashes across a network of shared VINs. For the moment, a poorly capitalized RRG with no guaranty fund backstop is supposed to write a check that covers the true cost of catastrophic harm.

Many RRGs in trucking do not want the minimum raised, not because of highway safety, but because of capitalization. If the minimum goes to $2 million or higher, thinly reserved RRGs face an existential threat. They’d need more capital. More reinsurance, if they can get it. Some couldn’t meet the requirements and would fold. That would force the carriers they insure to find coverage elsewhere. For many of those carriers, there is no elsewhere. They’d have to improve their operations or shut down.

From a highway safety perspective, that’s the feature.

The Gate

Insurance is not supposed to be a formality. It’s supposed to be the moment someone answers three questions: Who are you willing to hire? What equipment are you willing to put on the highway? Are you willing to be accountable when something goes wrong?

The captive model answers those questions every day. The best underwritten programs answer them on every application. The data now shows that large parts of the market have stopped asking them entirely.

In 1990, 5,174 people died in large truck crashes. In 2023, 4,354 people died. In between, we doubled the truck miles, tripled the carrier population, mandated ABS, ESC, and ELDs, reinvented passenger vehicle crashworthiness, and spent hundreds of billions on road engineering. All of it just to hold the line.

The people paying the price aren’t the carriers. They’re not the insurers. They’re not the RRG administrators or the RPG organizers. They’re Ashley Chapman on Route 17. They’re Henry, Menno, Paul, and Simon on State Road 67. They’re the five people on I-20 in Terrell. They’re the three people on the Florida Turnpike. They’re the 82% of fatalities in large truck crashes who are not truck drivers, passengers, pedestrians, cyclists, or people in other vehicles who never consented to share the highway with an operation that couldn’t pass underwriting at a single legitimate insurance company in America.

That’s what we’re scoring. That’s what we’re tracking. That’s what we’re going to keep exposing until the jet means something again.

The post Insurers Judged By The Trucking “Company” They Keep appeared first on FreightWaves.

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