For Chad Roberson, owner-operator of Chad Roberson Trucking in Fairfield, Illinois, trucking isn’t just a career — it’s a family tradition spanning three generations. At the heart of that tradition lies a 2000 Kenworth W900L, a truck that embodies perseverance, family pride, and countless miles of memories.
“My grandpa drove until he was 82, and my dad until he was 67,” Chad said. “I’m the third generation in this line of truckers, and the W900L is part of that legacy. It’s not just a truck — it represents everything my family has built, our struggles, and our successes.”
Chad’s passion for trucking began in childhood, inspired by his father, Everett, a full-time owner-operator, and his grandfather, Leo, who balanced life as a preacher with occasional trucking work. By the time Chad was 10, he was already learning the ropes, riding along with his dad on I-10 in Texas during summer breaks, imagining himself as the driver. “Those are memories that stick with you forever,” he said.
Though Chad initially pursued a different path, earning a basketball scholarship to Cincinnati Bible College with dreams of becoming a teacher and coach, the call of the road proved too strong. “Every time I heard a truck horn, I’d think of my dad and the road. I just couldn’t get trucking out of my head,” he said. Despite a few well-intentioned objections from his father, Chad established Chad Roberson Trucking in 1994 and began building his own career in the industry.
The W900L became a key part of the Roberson family’s story in 2000 when Everett custom-ordered it. Designed for both performance and style, the truck featured Kenworth’s 86-inch Studio Sleeper, a Signature 600 Cummins engine, 18-speed transmission, and a 285-inch wheelbase. Its standout feature was its bright yellow paint – a personal touch chosen by Everett’s wife, Marsha, who loved yellow roses.
“Dad let her choose it because she was traveling with him a lot more by then,” Chad said. “That truck wasn’t just his—it was theirs.”
For Chad, the W900L represented far more than its specs. “This truck is my family’s story on wheels,” he said. “When I sit in that seat, I feel them with me. It’s where my dad taught me about life, hard work, and pride in what you do. It’s where my mom showed me that trucking wasn’t just a man’s world. That Kenworth represents every lesson they taught me.”
Tragedy struck in 2004 when Marsha passed away suddenly from a heart attack. Grieving her loss, Everett considered retiring from trucking. To keep the W900L in the family, Chad purchased it from his father. However, Everett couldn’t stay off the road and reclaimed the truck. Just two months later, he passed away from colon cancer.
Devastated, Chad let the truck go. “I wasn’t in the right headspace,” he said. “When the bank asked if I wanted to buy it, I just couldn’t. I told them to sell it, and that’s how it ended up on a lot in Mount Vernon, Illinois.”
For nearly 15 years, the W900L was lost. “I regretted letting it go,” Chad admitted. “Dad had even put the truck and trailer on their tombstone — it was that meaningful to him. Letting it slip away felt like losing a piece of them.”
In 2022, fate intervened. While browsing an online marketplace, Chad came across a listing that stopped him in his tracks. “There it was — Dad’s truck!” he said. “The specs matched, and I recognized the pinstriping immediately. It had purple fenders now, but deep down, I knew it was his.”
Chad reached out to the sellers, a young couple, and shared the truck’s history. They explained that their neighbor had purchased it from the bank years ago before moving back to South America, leaving the truck in their care. After hearing Chad’s story, the couple insisted the W900L return to him. Two weeks later, Chad flew to Medford, Oregon, to reclaim the Kenworth.
“Driving it home, over 2,000 miles, was surreal,” he said. “I could feel Mom and Dad with me the whole way.”
Chad believes finding the truck was no coincidence. “I wasn’t even looking for it, but there it was, posted just 30 minutes before I saw it. My wife and I had just been talking about the truck the day before,” he said. “It’s like everything fell into place at the perfect moment. Whether it was Dad, Mom, or someone else, I’m grateful for whoever made it happen.”
Since bringing the truck home, Chad has begun restoring it. He’s replaced the stacks, added new fuel tanks, smoothed out a few dents, and is redoing the paint to bring it back to its original glory. “I’ll incorporate a little bit of myself, but it’ll always be Dad’s truck. His CB handle, ‘Rockin’ Robin,’ is going back on it, along with Mom’s, ‘Green Eyes.’ This truck was theirs, and I’ll honor that,” said Chad.
Though Chad currently drives a 2019 Kenworth T680, primarily hauling produce to Walmart distribution centers across the Midwest, the W900L holds a special place in his heart.
“This truck has stood the test of time. It’s more than a truck — it’s my family’s legacy. It’s every mile my dad drove to provide for us, every moment my mom spent riding along, and every lesson they taught me about life,” said Chad. “When I’m behind the wheel of that Kenworth, I’m keeping their memory alive.”
Rolling On: Behind the Wheel with Chad Roberson, Alabama, and Kenworth
When truckers talk about the music of the road, one band always comes to mind: Alabama. Their songs have echoed through countless cabs, fueling long hauls and late nights. For Chad, their music wasn’t just background noise — it marked the miles he lived.
“I wore out Alabama tapes in Dad’s truck,” Chad said with a laugh. “Their music just fit — it kept us going.”
One of Chad’s fondest memories of the band was seeing them perform at the Mid-America Trucking Show with his parents. “It felt like they belonged to us truckers — their songs just resonated with life on the road.”
Decades later, that connection came full circle in a way Chad never imagined. Through a friendship with Josh Gentry — the son of Alabama’s bass player, Teddy Gentry — Chad found himself with the opportunity of a lifetime: driving for the band. “Josh and I met at a truck wash in Mount Vernon, Illinois,” Chad recalled. “We stayed in touch, and one day, he called me and said they needed an extra driver for one of Alabama’s tours. I couldn’t say yes fast enough.”
Chad’s first run with Alabama was as a team driver with Josh, hauling the band’s gear in a 2021 Kenworth T680. Their travels took them across the U.S. and into Canada, delivering everything needed to keep the show going.
“Alabama and Kenworth just go together,” Chad said. “For as long as I can remember, their gear has been hauled by Kenworths. It says a lot about the reliability and quality of the brand that they’ve stuck with it for so long.”
One particular tour stood out to Chad: the Kenworth-sponsored “Roll On II Tour,” named after Alabama’s 1984 hit, “Roll On (Eighteen Wheeler).” The song, already an anthem for truckers, made the tour feel especially meaningful.
“Hearing them play that live while helping make it all happen was something I’ll never forget,” Chad said. “It was like everything in my life had come full circle.”
One of the highlights of Chad’s time with Alabama came when he had the chance to visit Kenworth’s Renton manufacturing plant this past September. “That was like a dream on top of a dream,” he said.
Looking back, Chad reflects on how much Alabama’s music has shaped his life – and how everything seems to have aligned perfectly. “They’re more than a band to me — they’re part of my story.”
