If you work anywhere near trucking insurance right now, you’ve heard the name Montgomery more times this year than you probably expected to. The Supreme Court case shook up how liability gets assigned across the transportation supply chain, and the aftershocks are still landing. So what actually changed, what didn’t, and what should insurance professionals be doing about it right now?
MCIEF Education Director Beverly Raiford sat down with J.W. Taylor, Managing Partner at Taylor Nelson Slattery Bernard PL, to dig into exactly that. J.W. is a returning speaker at the 2026 MCIEF Leadership Conference in Scottsdale, where he’ll lead a session called Persistent Trucking Issues. This conversation is a good place to start if you want a preview of what he’ll bring to the stage.
Why a Trucking Attorney Belongs at an Insurance Conference
Beverly asked J.W. directly why insurance professionals should care what someone on the legal side thinks. His answer cuts right to something MCIEF has been saying for years: insurance and transportation aren’t two separate worlds, they’re the same world wearing different hats.
“It’s important to transportation and logistics because it’s important to insurance. They’re one and the same,” J.W. said. “One does not function without the other, and when we separate them out into silos, that’s when we get in trouble.”
That’s the whole premise behind bringing a legal voice into a room full of underwriters, brokers, and claims professionals. The people writing policies and the people arguing cases in court are dealing with the exact same set of problems, just from different angles.
Living in the Post-Montgomery World
The biggest reason J.W.’s session matters this year comes down to timing. The Montgomery decision, and the wave of related cases that followed it, changed how liability gets assigned when something goes wrong on the road. J.W. says the industry is still sorting out the practical fallout.
“We now live in the post-Montgomery world,” J.W. said. “I want to talk about what changed, what didn’t, and especially what now? Because all of the insureds out there are going, ‘What now?’”
That last question, “what now,” is really the heart of his session. Plenty of people have talked about what Montgomery means in theory. J.W.’s value at the Leadership Conference is walking the room through what it means in practice, for underwriting decisions, for claims handling, and for how carriers and brokers manage risk going forward.
He Predicts It’ll Make the Top 10 List
Each year, MCIEF surveys the industry to identify the Top Trucking Insurance Industry Issues, a list that runs alongside ATRI’s own top industry issues report. J.W. made a pretty confident prediction about this year’s list.
“I make a prediction that on our top five or top 10, whatever ends up being critical issues, there’s going to be one added, or some form of one added, about the post-Montgomery industry,” he said. “Here’s the good news. If you’re looking to attend, we’re going to beat it to the punch, because I’m going to be talking about that at this assembly.”
In other words, whatever ends up trending on the survey results, J.W.’s session will likely already be ahead of it.
A Room Full of Young Leadership
J.W. has spoken at MCIEF events for years, and one thing keeps bringing him back: the age of the room. He talked about what it looks like from the stage, looking out at attendees who represent the next generation of trucking insurance leadership, not the last one.
“It really strikes me how young the MCIEF membership is, and that jazzes me,” he said. “The leadership of the future is sitting right there in the room. Don’t you want to be a part of that? I know I do.”
He connected that point to something bigger happening on the legal side of the industry. Plaintiffs’ attorneys, as J.W. put it, are already sharing perspectives, sharing discovery, sharing everything with each other. His argument is simple: the insurance side needs that same kind of collaboration and knowledge-sharing, and events like the Leadership Conference are where that actually happens.
His Advice for Anyone on the Fence
When Beverly asked what he’d say to someone considering the trip to Scottsdale, J.W. didn’t hesitate, he borrowed a line from Yoda: “There’s no think, but do.”
It’s a simple way of saying the same thing plenty of past attendees say after the fact: the conversations, the networking, and the practical takeaways are worth more in person than they ever are secondhand.
What This Means for You
If your work touches trucking risk in any way, underwriting, claims, broker relationships, or carrier advising, the legal ground under that work has shifted, and it’s still shifting. J.W.’s session gives you a chance to hear directly from someone arguing these cases, not just reading about the headlines.
He’ll be leading the Persistent Trucking Issues session at this year’s Leadership Conference, building on the post-Montgomery conversation he previewed with Beverly, and likely previewing where the industry’s next Top 10 list is headed before the survey results are even out.
Join Us in Scottsdale
The 2026 MCIEF Leadership Conference runs October 4 through 7 at the Grand Hyatt Scottsdale Resort. Along with J.W. Taylor’s session, the agenda includes the MCIEF Top Trucking Insurance Industry Issues discussion, the State of the Market Report, and plenty of built-in time for the kind of networking J.W. says matters just as much as anything said from the stage.
If you want to walk into next year already ahead of the post-Montgomery conversation instead of playing catch-up, this is where that happens. Register for the 2026 MCIEF Leadership Conference and reserve your seat in Scottsdale this October.
One more thing: the discounted hotel block at the Grand Hyatt Scottsdale Resort closes September 9, 2026. If Scottsdale is on your calendar this October, don’t wait on the room booking.
Not yet an MCIEF member? Membership gets you access to events like this one, along with the TRS and TCS designation programs and year-round continuing education built specifically for trucking insurance professionals. Visit mcief.org to learn more about membership and how to get involved.