We're down to the wire on the new year -- due time to celebrate what's been a 2025 full of inspiring stories of triumph over adversity for so many of our Trucker of the Year contenders. With 10 Truckers of the Month named through October and all bringing unique approaches to their owner-operator trucking businesses to the table, the last couple months of the year have been especially difficult for those we call on to be judges for the competition.
"All of these owner-operators are successful," wrote one of those judges, noting difficulty truly separating the 10 from each other, particularly when you start to think about a top three or even a winner.
Overdrive's 2025 Trucker of the Year competition featured "perhaps the strongest field of candidates we’ve ever seen," said another, "which made judging that much more difficult."
All brought unique qualities to the table distinguishing them for the top honor, whether fuel efficiency far and away above the crowd, a keen focus on cost containment elsewhere or winning ways with customer service toward building business to sustain. For those at the very top of the list here, it's real performance in some ways that drove judges' ratings, inching them higher and higher up the rankings.
[Related: Compete for Overdrive's 2026 Trucker of the Year honor]
Results follow evaluation of each individual owner's history, testimony from references like customers and vendors, and financials submitted, most often for the prior year. If you missed our recent catch-up with eight of the final 10 semi-finalists, you can hear late-year updates and glean plenty in the way of advice from the two-part series of "exit interviews," roundtable talks broadcast via the Overdrive Radio podcast.
Now, without further ado, three finalists advance into the final round toward the Trucker of the Year honor:
Ron Kelsey, Arizona
One of Overdrive's Trucker of the Year judges positively gushed over the holy grail the Kelsey's Trucking flatbedder's achieved: "He's crushing it. I want to be Ron Kelsey when I grow up." That is, an independent owner-operator with direct customer relationships that date back more than three decades and a pristine 1981 Peterbilt 359 with millions of miles behind it but looking better and running as well or better than it did when Ronald Reagan was president. That's when Kelsey bought the unit, repowered with an electronically-controlled engine in the 1990s. The rig's served him well these many years, and Kelsey's slowed down in recent times, now in his fifth decade trucking. Importantly, he can afford to take as much time off as he likes, having banked profits through the years that set him up to enjoy life to the fullest. Read all about the 359 and the superlatives Kelsey's customers threw the owner-operator's way via this link to the July Trucker of the Month feature about the business. As the judge quoted above said about his 10 out of 10 rating for Kelsey's biz, "I know 'SuperTrucker' is generally seen as derogatory, but Kelsey should put on a cape and teach owner-operator clinics."
John Penn, Indiana
Joining Ron Kelsey as finalist for the 2025 Trucker of the Year award is owner-operator John Penn, whose J.P. Transport independent business loads steady outbound from Indiana at a furniture manufacturer for LTL multi-stop runs, mostly west and south. Established more than a decade ago, Penn's business follows early-century experience as a company driver of hazmat tankers and a move to step deck freight with his first truck, a 1990s fully mechanical International. He's upgraded several times since in pursuit of reduction in the biggest operating expense for any owner. With Penn's current 2019 Freightliner Cascadia, purchased used, and plenty aero modifications to his van trailers, he wrings out 11-plus miles per gallon, outperforming much of his competition in that department. As did some of his business partners and peers in our October Trucker of the Month feature about his business, one judge recognized in Penn a "true student of the trucking business with a desire to improve and learn." Penn's clearly got the "personal drive to not only work at being profitable now, but for years to come. The numbers don’t lie. John has learned what I think might be one of the hardest lessons of all -- how to work smarter, not harder." More about J.P. Transport.
Jason Shelly, Pennsylvania
Owner-operator Jason Shelly's refrigerated loads, like Penn's LTL furniture runs, originate at a single pickup point but are multi-stop on the delivery, in Shelly's case fresh meat headed to Amish markets along the East Coast. It's a trucking niche he built over many years as an independent -- his was the first large-truck business to serve the meat producer hauling out to metro areas from his Pennsylvania home base in Lancaster County. Judges recognized a savvy business owner, not only for long service to a "niche he practically invented," in the words of one, but also efforts to cement "strong relationships in his community, and treating customers to the superior kind of service so crucially needed in the food service supply chain." Shelly knows his way around a truck, too, as is evidenced in the images above of units he's worked on and/or hauled with throughout the years. His current '07 Western Star started its life as car hauler that he turned into the beauty you see above, "the coolest truck" in the field, according to another among Trucker of the Year judges. Following in the footsteps of an owner-operator father who's involved in the son's business today with bookkeeping and other assists, Shelly's taken the father's example with an S Corp structure, accounting for his and dad's compensation on the cost side of the ledger, yielding tax savings he's investing in the future of his business and, most importantly, his family. More about Jason Shelly at this link.
Keep tuned in January for announcement of the winner, and meantime take opportunity over the holidays to dig into the stories of all of the competitors honored throughout the year. Find podcasts featuring all 10 in the Overdrive Radio playlist below, followed by more about each exemplary owner-operator.
Entries are open: Enter your owner-operator business in the 2026 Trucker of the Year competition.
The rest of the Trucker of the Year semi-finalist field follows. Congrats to all for the well-deserved honor:
Ken Brodeur, California
Owner-operator Brodeur takes pride in not only his ability to maintain profitability as one man, one truck, one trailer, but also to make it in the regulatory hotbed that has been the state of California over his time at the wheel of the business. Trucker of the Year judges noted his example as an inspiring second-career tale "proving age isn't a hindrance to start-up and long-term success trucking as an owner-operator." Brodeur, 55 years old when he bought his first truck, has followed his own advice for anyone who asks about taking up trucking as an owner-operator: "Learn to be smart," he said. "To operate a small business in this country, I don’t care what you do, you have to be pretty savvy, which means you’ve got to think, you’ve got to learn.” More about Brodeur at this link.
Hunter Hubbard, Virginia
The before-and-after shots across the top of the image above of Hunter Hubbard's 2005 Kenworth W900B dump truck tell the tale of the woman behind the now-three-truck Dice Mayhem's Trucking and Dice Logistics side OTR business for seasonal dump downtime. She does it all, from the paving and construction site work on the dump side to wrangling customers with her husband, Tim Hubbard, and keeping the equipment in tip-top shape -- her W900B dump, "Smurfette" she calls it, is also a finalist this year in Overdrive's Pride & Polish virtual truck show. Among Trucker of the Year judges, one noted Hunter Hubbard's "keep digging on it" mantra for persistence, noting the Hubbards are "knocking it out of the park with what they're doing, stacking 100s, and that’s the name of the game. Grind on, Hunter!" Read more about Hubbard at this link.
George Kincaid, West Virginia
Truckin's not easy. Those few words might well sum up the single acknowledgment of business difficulty independent owner-operator George Kincaid is willing to muster in delivering advice to younger sorts coming up behind him in business with one truck and a dream of success. In our April Trucker of the Month feature about the West Virginia flatbedder, he followed that up with "don’t give up. You've got to be persistent. There will be rejections and rough patches, but keep an eye on the big picture and where you want to be. Keep your eye on your goal, and don’t let the little stuff" derail you. "You’ll look back on it and laugh, ultimately." Kincaid trucks in this 2001 4900EX Millennial Edition Western Star hauling for regular customers/brokers, and competition judges in particular lauded his mechanical aptitude, enabling him to effectively contain costs by doing the lion's share of the work himself. Truckin' might be hard, indeed, yet Kincaid's clearly doing it right. More about his operation at this link.
Rufus Morris, North Carolina
Owner-operator Morris (pictured with his wife and business partner, Patricia) launched Midnight Rider Transport with his own authority, building a strong relationship with the company for whom he now hauls often-oversize flatbed freight in a leased arrangement, Material Logistics Management. As with George Kincaid, Morris has made strides with a do-it-yourself maintenance approach. It's delivered him from numerous roadside situations, though in 2025 a slightly earlier-than-expected engine rebuild for his 2004 379's Caterpillar power plant set him back a bit from his income goal for the year. He's taken it in stride, though, with consistency in freight and a knack for a tight ship for his pre-planned loads, on-time every time, no matter the roadblocks in the way. One judge extolled Morris's "example of quiet confidence and positivity" as a "breath of fresh air. Some people just go out there and get it done, despite what the politicians are doing." His example is "yet another study in the importance of doing such a good job that someone will pick up the phone and ask how they can work with you more." More about the Morrises and Midnight Rider via this link.
Scott Smith, Arkansas
Sapphire Cartage owner-operator Smith values his downtime for family -- rather than let his power unit take over his home life, in 2023 he purchased two near-identical 2017 Peterbilt 579s powered by Paccar MX13 motors, using one as a spare when his go-to mechanic has the other. And his hopper work hauling rice, various grains, meals, dried peas and all manner of ag freight through years has kept him in the black. This year, though, as we told in this June Trucker of the Month feature, he's switched to flatbed work after seeing the decline in income with the hopper. It's gone well over 2025, by and large, and Smith well knows it. He religiously uses a custom spreadsheet to track profits load-by-load, week by week. He and his wife, Stephanie, built the tool for analysis, impressing judges with its specificity, particuarly for analysis of per-ton rates that come with hopper work and meeting home needs with a weekly owner's draw on the cost side of the profit calculation. His attention to numbers led to a decision to give back toward the end of 2025, when he brought on a driver for the second Pete to dip his toes into small fleet management, and deliver gains back to a friend and longtime mentor nearing OTR retirement. More about Sapphire Cartage.
John Treadway, Indiana
Dreams inspired by owner-operators as a kid in his native Indiana propelled Treadway on the path to independence with Tway Rose Transport, serving a flowers distributor in his area with a spectacularly memorable rig -- the 1998 "Teal Appeal" 379 and matching reefer you see in the images here. 2025 saw the unit voted in as a finalist in Overdrive's Pride & Polish in addition to Treadway's business' Trucker of the Month honor in September. The year wasn't without setbacks, though, as a late-year engine failure for Teal Appeal sidelined the unit. Like Scott Smith, though, Treadway was prepped for that with spare power as he worked to swap the Caterpillar with a reman, with further plans to rebuild the original engine down the line. One among the judges gave kudos to Treadway for following his own advice for the next generation in line behind him. Namely, prep for the future when the hard times will surely come. More about Tway Rose Transport and Treadway.
Kenny Wingate, Florida
Finally, last but far from least is the Southpoint Exchange two-truck reefer business of Kenny Wingate, serving longtime trusted brokers on lanes between his state and the Midwest. It's one of those brokers, in fact, that nominated Wingate for the Trucker of the Year honor to kick off 2025, in fact. One among judges found old-school approaches yielding big dividends for the owner as he put in motion plans for a third truck in the operation. Wingate's "brand of courtesy, competence and professionalism would have easily landed him as a finalist" in other years for the Trucker of the Year competition, the judge noted, with Wingate cementing his LTL delivery as a real "throwback to a time when the brokers loaded the man based on reputation and real performance, as opposed to just some digital profile on a screen." Wingate clearly inspires confidence in his and brokers' customers, and he's made fuel-mileage strides in recent years, too, in efforts to contain costs in LTL, "the special forces of trucking," the judge noted. Wingate's in it for the long haul. As he put it early in the year: "There’s no feeling like being an owner-operator," he said. More about Wingate and Southpoint Exchange.
Enter your owner-operator business in the 2026 Trucker of the Year competition.
