As he approached his 23rd birthday some 35 years ago, Gary Williams was seeking a path for his future that would make a college education a reality. At that time, the United States Army’s recruiting pitch highlighted money for college.
That sounded good to Williams. So, he walked through a door of opportunity that, over the next 31 years, offered much more than funding for books and tuition.
Looking back over a military service career in which he rose to become a Command Sergeant Major while being called to some of the world’s hotspots — including Iraq as a Chief Medical NCO — Williams knows his three-plus decades in the Army provided him with a doctorate level in field experience on how to be a leader and problem solver.
Following his retirement from the Army, Williams kept his eyes open for a role that could possibly be a new “field command.”
He discovered trucking as the ideal next chapter and, despite knowing that he would hold the rank of rookie as a freshly minted professional driver in his first job, the opportunity he was offered by Stevens Transport perfectly spoke to the retired Sergeant Major’s desire to use his experience and be in charge of his destiny.
Nominated by Stevens Transport for Transition Trucking’s 2026 Driving For Excellence Award and selected as one of the Elite 11 semifinalists for the honor, Williams is quick to credit his years in the Army.
He says the whole experience started with seeing a TV ad for the Army. That was the key that opened the door to understanding the kind of service and leadership that is truly life-changing.
US Army TV ad inspires a calling for a born leader
“It was the middle of Desert Storm. A commercial came on TV and said, ‘Join the Army, get the Army college fund and go back to school.’ So, I called the recruiter and that was kind of the beginning of it,” recalled Williams. “It’s kind of embarrassing to say that I joined to get the college money. But, after you do 31 years in the military, I learned what it meant to serve.”
Gary William’s interview video appears below. Readers may also click here to view the video on YouTube or click here to hear an audio-only version.
As he shares with PodWheels in his Elite 11 Spotlight Interview, Williams would be called to put all his skills, talents and experience to the ultimate test as a medic when he deployed with his field unit to Iraq.
Williams was stationed as the first unit after the immediate care at the front. Unfortunately, the wounded personnel that Williams’ team first encountered were casualties who couldn’t benefit from their help. His care team became frustrated. They wanted to apply their life-saving field skills to get the wounded to the next stage of care.
“They were asking me, ‘What are we doing?’ I had to lead them through that process of just reassuring them that there are going to be people that we can help,” Williams said of the Iraq field deployment.
“I had them go back to their training, reemphasizing during their training: ‘We will get casualties that we can help. And when we do, we will help them,’ he said. “So, it came to fruition that eventually things kind of normalized and we started getting soldiers in that we could help and we got them where they needed to be.
“It’s just kind of lessons in life. Just always be persistent, always go with your training,” he continued. “You need to understand that, if you keep on that standard, you’re going to be successful regardless of how things go at first. You just have to keep plugging away.”
A new calling and family support
This past January, Williams took the leap to restart his career path, shifting from being an experienced trainer stationed in the world’s hot spots to a trainee ready to learn what it takes to become a professional driver.
It was during his time at Southern Careers Institute that Williams met a representative from Stevens Transport and a connection was made.
“While I was at the school, I was able to meet Charles Wages (a recruiting manager and field recruiter for Stevens Transport) and talk with him to learn a little bit more about Stevens,” recalled Williams. “They were obviously on my radar as soon as I started looking at trucking. I found Stevens to be just the right fit for the kind of work that I wanted to do. Even though I’m working for Stevens, I’m still kind of my own boss every day.
“They tell me where I’ve got to be and when I’ve got to be there. It’s up to me to get there,” he continued. “After being in the military for such a long time and being at a high rank, I was looking for something where I’m just in charge of myself. I have the autonomy to make decisions and run my day-to-day operations.”
In addition to the Stevens team, Williams has the support of his family as he captains his rig across the nation’s highways.
He is quick to credit wife, Sherry — who kept their home running with military precision for their family while he was in the Army — for her vital role in his transition to trucking.
“I had her support all the way through the Army. Our four kids have grown up to become such phenomenal people. I could not have had the career in the Army without her,” Williams said.
“When it came to considering trucking, Sherry said, ‘If that’s what you want to do, then I’ll support it,’” he continued. “She just asked me to not stay out on the road too long, and Stevens has been very supportive in getting me home about every three weeks.”
A special salute made with small hands
During his conversation with PodWheels, Williams explained that one of the joys of his transition into trucking has been the opportunity to share his experiences with his grandchildren.
His oldest grandchild, Allison, was so inspired upon seeing Grandpa Gary behind the wheel of his big rig that she drew a picture that now occupies a special spot inside the cab of his Stevens truck.
For Williams, Allison’s drawing serves as a salute to his transition to trucking that always brings a smile to his face.
“One of my most prized possessions is something she stuck in my suitcase before I left last time,” said Williams of Allison’s artwork. “It’s a drawing of me and her in front of the truck. It’s in the truck, and I look at it every day.”
Williams will no doubt carry the keepsake his granddaughter created as he travels to Columbus, Ohio, on Sept. 22, when Transition Trucking’s 2026 Elite 11 will gather at the National Veterans Memorial and Museum.
Since first getting behind the wheel for Stevens in February to becoming a member of the Elite 11 in August, Williams has enjoyed quite the rookie year in trucking.
“My transition to trucking has gone pretty smoothly — a lot smoother than I had dreamed. But I still have some work to do,” said Williams. “It’s great being a part of the Stevens team, and it’s great to be a part of the Elite 11. All of them are well-deserving people, and it’s great to be mentioned in the same breath as them. All of this has been a real blessing.”
TheTrucker.com, in collaboration with PodWheels, is launching a series of feature stories highlighting the Elite 11, the semifinalists in the running for the Transition Trucking: Driving For Excellence Award. Our series will spotlight each member of the Elite 11 ahead of Transition Trucking’s Special event on Sept. 22 at the National Veterans Memorial and Museum in Columbus, Ohio. Follow The Trucker and PodWheels for more coverage of the 2026 Transition Trucking event.
Greg Thompson is an award-winning writer and producer who has worked in the trucking industry in a variety of roles since 1998. With more than a decade’s worth of experience as a journalist prior entering trucking, Greg is the founder and executive producer of PodWheels.com, a podcast network dedicated to spotlighting the trucking industry.
Since 2019, PodWheels has provided specialized coverage of the National Truck Driving and National Step Van Driving Championships.
In 2025, PodWheels’ NTDC Series earned the honor of being named the official podcast of the National Championships by the American Trucking Associations, which hosts the annual nationwide competition.
During 2025 alone, PodWheels produced some 100 episodes and provided over 50 hours of podcast content highlighting the competitors, organizers and volunteers involved with the Truck Driving Championships at both the state and national levels. PodWheels’ coverage of the NTDC, including state competitions and other features, is available through RoadToNTDC.com.
