Ever since he was a kid, Gregg says he has been enamored with trucks, truck drivers and the industry. At the age of 6, he visited the Vince Lombardi Memorial truck stop in New Jersey and asked truck drivers for their autographs.

But that dream took a backseat to his career as a U.S. Army officer after he attended and graduated from the U.S. Military Academy at West Point. For 28 years, Gregg served in the U.S. Army, became an Airborne Ranger and was deployed six times for overseas missions in Iraq and Kuwait, Haiti, Kosovo, Afghanistan and Libya. During his nearly three decades of service, he earned three bronze stars, a Legion of Merit, Defense Meritorious service medal, and a number of other service and combat badges, decorations and medals.

As he approached retirement age, Softy considered some post-military second career options, but always came back to his lifelong dream of becoming a truck driver. After discussing it with his wife, Gregg chose to take advantage of Stevens Transport’s Operation Patriot apprenticeship program, which is approved by IMCOM (the U.S. Army’s Installation Management Command).

The program allowed Gregg to complete his driver training in Ranger, Texas, and obtain his CDL, while still serving in the military. Available to active duty soldiers on several military installations, Stevens Transport covers the cost of training. Then, when the soldiers retire or complete their tour of duty, they can go to work for Stevens, which pays them up to $50,000 in the first year. A soldier-turned-driver can also earn an additional apprenticeship bonus of a little over $20,000. Here are links to some additional information about Stevens Transport’s program for veterans – visit http://www.becomeadriver.com/veterans/ or http://info.stevenstransport.com/stevens-military-vet-hiring-ub/

Last year after he started driving for Stevens Transport, Gregg first learned at the Great American Trucking Show in Dallas that he was chosen as one of three finalists out of a field of more than 10,000 nominations for the 2017 Transition Trucking: Driving for Excellence Award. The award is sponsored by the U.S. Chamber of Commerce Foundation’s Hiring Our Heroes Program, FASTPORT and Kenworth.

Then in December, a little over a week before Christmas, Gregg learned he had been chosen for thetop military veteran rookie driver honor during a special ceremony at the U.S. Chamber of Commerce in Washington, D.C.

It’s just after 10:30 on Friday evening and truck driver Rick Keiner waits patiently outside the sold out Keller Auditorium in Portland, OR.

As a cool breeze blows through his long beard, Keiner notices me peeking around his 2016 Kenworth T680.

“Can I help you?” he asks.

One moment earlier, I was one of 3,000 people enjoying an evening of soulful blues music with the Tedeschi Trucks Band, featuring the husband-wife guitar team of Derek Trucks and Susan Tedeschi.

Now I’m face-to-face with one of the most important pieces of band: the driver with Janco LTD responsible for transporting the gear for the 12-piece ensemble.

The rock 'n' roll trucker has long been of interest to me. I’ve had mixed success engaging them in conversation over the years. I often think they expect me to ask for a backstage pass.

July, 2017  Believe it or not, once upon a time I had a job driving trucks.

This was back in the early 1990s, right after I got out of college. I went to work for a brand-new marketing firm that targeted trade shows nationally. The entry-level job was an “Operations Manager.” It was a fancy title. But basically you did everything around the place except for janitorial work – including driving trucks to trade shows all over the country.

I didn’t have a CDL then – mainly because the company was too cheap to pay for it – and it didn’t really need Class 8 hauling capacity, either. Instead, it rented Class 7 straight trucks from the local Ryder dealer, and we took those out on the open highway to wherever we needed to go: Vegas, Orlando, Miami, Chicago, Anaheim… And a funky little truck show in Louisville, Kentucky, that we bitched about incessantly. At the time, I had no idea what a fixture that truck show would become in my life a few years down the road.

Looking back on it, it was a pretty miserable experience. I lasted a bit more than a year-and-a-half – and it surprises me today that I made it that long. But I’m stubborn like that.

The company told us all the time that because we were a startup, we needed to operate smart and cheap. But the reality was we were running just a shade inside of the law. Looking back on it, we were lucky no one got hurt. Or worse.

To be fair to Ryder, the cabover trucks we were in weren’t even remotely spec’d for long-haul driving. No cruise control. Bench seats (the passenger seat could not be adjusted). AM radios. And manual transmissions – although they were automotive-grade, so at least we didn’t have to deal with double-clutching and high/low ranges. And the trucks were governed to about 65 mph. 

All that said, driving was my favorite part of the job. I didn’t mind being alone. And I definitely liked being way beyond the reach of any bosses dreaming up stuff for me to do. Plus, it was a pretty cool way to see the country first-hand. Much different than looking down at it from an airplane seat the way I do today. I never really considered truck driving as a career. But I don’t think I would’ve minded it a lot if that’s what I’d wound up doing. It wasn’t the worst job I ever had. It could’ve easily been made a lot better if I’d been given better equipment. And I can think of way worse ways to make a living.

At the time, I never would have thought I’d one day wind up being a journalist covering the North American trucking industry. And it’s funny how often I think back on that brief time behind the wheel when I’m talking to drivers, or fleet and OEM executives today.

For example, you don’t have to sell me too hard on the value of ergonomics, driver comfort features or safety systems. I understand the strain drivers feel being away from loved ones for long periods and missing important holidays and events. I have some real-world insight into the prejudices the driving public holds against trucks and truck drivers. And I totally understand when drivers say they’d like fewer rules and regulations dictating how they do their jobs. And I really get it when they say they don’t like Big Brother sitting in the cab with them looking over their shoulder.

A lot has changed since my brief stint on the nation’s highways. But a lot of the core issues and pain points drivers face today have not.

But there’s no doubt the equipment today has gotten light-years better – and safer – than it was 20 years ago. I can’t match their miles or their experience, but I can’t help but smile when I hear old school drivers today tell newbies they don’t know how good they have it. Because they don’t.