Walter Jackson, an independent Landstar owner-operator, has been recognized by the Truckload Carriers Association (TCA) as one of their five Professional Drivers of the Year for 2025. His inspiring journey began over four decades ago and showcases dedication, resilience, and a passion for trucking.
Jackson shared his story recently through a Landstar blog post, giving insight into the roots of his trucking career.
A Childhood Marked by Grease and a Wooden Spoon
Jackson traces his trucking journey back 46 years to when he was just five years old. He recalls, “It all started 46 years ago, when I was just 5 years old … with a smear of grease and a wooden spoon.”
As a child, he helped his father and grandfather while they worked on their trucks, fetching water and coffee for them. “In return, they would put a little smear of grease on my arm to signify I was their helper,” he explained. “I wore that grease stain with pride.”
Over time, he progressed from helper to “wrench grabber,” earning short rides in his father’s truck to nearby terminals to pick up loads. “Before leaving, I would sneak a wooden cooking spoon from the kitchen, sit in the sleeper and simulate my father shifting gears,” Jackson remembered.
The moment he got to practice shifting “for real” beside his father was pivotal. Standing near the driver’s seat, moving the gear stick up and down, he was hooked. “That was it! I was sold on becoming a truck driver,” he said.
Building a Career Through Trials and Triumphs
Jackson began driving professionally at 23, and in 1998, with family support, he purchased his first truck.
However, in 2005, Hurricane Katrina brought immense challenges. Forced to evacuate New Orleans, Jackson was hauling blue tarps for a Landstar agent contracted by the U.S. Department of Transportation. Reflecting on that time, he said, “I wasn’t prepared for what I saw once I was able to work my way into the city with relief supplies. We lost everything!”
In response, Landstar offered financial support through their BCO Benevolence Fund, established in 2005 to aid owner-operators in times of crisis. Jackson expressed gratitude, stating, “That (assistance) spoke volumes about the company I had just leased to. I knew I was going to be here until I retire.”
Now in his 21st year with Landstar, Jackson plans to donate a portion of his $20,000 prize from the TCA Professional Driver of the Year award back to the Benevolence Fund.
Giving Back Through Service and Mentorship
Jackson’s commitment to the trucking community extends beyond his own success. After Hurricane Harvey struck Texas in 2017, he actively hauled disaster relief loads. Later, he spent 16 months in Puerto Rico helping coordinate fuel truck dispatch and deliveries following Hurricane Irma. “I thought I’d spend a month or two, but ended up staying for 16 months,” he said.
Back stateside in 2019, Jackson expanded his business by leasing additional trucks to provide opportunities for other drivers to build experience and income.
During the COVID-19 pandemic, despite supply shortages and many trucks being sidelined, Jackson increased his fleet size to keep others on the road. “I chose to stay on the road among other ‘essential workers,’” he noted.
Now a small-fleet owner, Jackson focuses on mentoring new operators. He helps them with credit, setting up business accounts, and selecting the right truck. “I strive to prepare newer operators for success in their own truck someday,” he said.
Safety as a Cornerstone of Professionalism
For Jackson, safety is paramount. “You’re not just driving for you, but also for everyone around you,” he emphasized. “As a professional driver, it’s my duty to make sure everyone around me remains safe. A professional maintains a clear vision of their surroundings, obstacles, potential hazards, and has an emergency plan of action at any given moment.”
He also enjoys the simple moments of the road, saying, “I like to ride in the right lane in a clean, shiny truck, especially when I see a kid in a car rolling up, pumping an arm up and down as a signal for me to toot the air horn.”
Owning 12 trucks today, Jackson’s passion still connects him to his roots — the grease on his arm and shifting a spoon in his mother’s kitchen.
Image Source: Landstar Systems Inc.
Source: Ginger Jewell, Landstar Corporate Communications, Truckload Authority Staff, The Trucker
