Give a round of applause for Overdrive’s 2025 Trucker of the Year, selected from a field of 10 semi-finalist Trucker of the Month honorees, then three finalists.
Off the top of the Overdrive Radio podcast here, the winning independent's freight partners laud Penn for core strengths in his day-to-day work for a dedicated customer of the brokerage and small fleet Rankin & Sons.
"I can't think of anyone who deserves it as much as he does," said Jeanna Bean of 2025 Trucker of the Year John Penn.
We also spoke with a close associate of Penn, Schneider-leased owner-operator Kevin O’Sullivan of Arizona, who recognized the real strength of the competitive field of all of our 2025 Truckers of the Month, especially the two fellow finalists.
"There was a lot of good competition," said O'Sullivan, yet Penn "came out on top, and I'm glad he did. That man is a wealth of knowledge and everything he's learned, the good and bad, he's definitely not afraid to put it out there and help other people."
If you followed the 2025 competition, you'll remember owner-operator John Penn's story. Trucker of the Year judges in the final round praised Penn for qualities shared by his fellow finalists -- drive, clear focus on and execution of long-term business stability, mechanical aptitude, and so much more.
What may well set him apart, though, is what he’s done to take advantage of benefits late-model engines and drivetrains spec'd just right for maximum fuel economy. Penn hovers near and occasionally above 11 miles per gallon routinely in his 2019 Freightliner Cascadia, bought used some time back now.
Penn’s worked hard to understand contemporary emissions controls and other maintenance peculiarities. Profits improved with the best mpg, he avoids undue maintenance by eliminating idling at any cost, among other things.
All of it shows in his one-truck business’s very-low operating ratio.
Penn hauls LTL furniture with own authority as JP Transport, those outbound dedicated runs for Rankin & Sons' customer, whom he treats like his own. He's hard at work taking advantage of return-load opportunities for possibly dedicated freight coming back toward home in Orleans, which you'll hear more about in a follow-up Overdrive Radio edition with the owner.
In this episode, John Penn gives credit where credit's due, telling the stories of some of the men who mentored him early in trucking, and who inspire him today -- including competitors Ron Kelsey and Jason Shelly.
"I was shocked, first of all. Honored," Penn said of learning of the win, particularly alongside Kelsey and Shelly, both of whom he felt were, simply put, "the top of the heap."
As prize for the win, John Penn will be the proud owner of a Bostrom Seat from the Trucker of the Year program sponsor as well as a scale-model version of his aerodynamic 2019 Freightliner Cascadia by Eston Hoffman of Hoffman Mechanical Design. Plenty bragging rights, too, for the time to come.
As O’Sullivan puts it, referencing Penn’s fuel-mileage excellence in particular, "he's certainly set the bar high for the rest of us." O'Sullivan offered three words to describe his friend, mentor and potential future business partner: Informative, genuine, down-to-earth, qualities that underpin John Penn’s two-decade odyssey toward stability and profit with authority.
In the podcast, Penn tells his story, by way of an appreciation for the people in his life who’ve been there setting him straight on the course to success, giving credit where credit's due:
Penn with his wife, Pamela -- in the podcast, the Trucker of the Year also shares the pair's origin story dating back two decades; they share more than just a personal bond. Pamela spent years a small-biz owner herself, as you'll hear.
Keep tuned for more from Penn in the coming weeks, likewise ways you might meet him at the Mid-America Trucking Show in March. Enter your own or another owner-operator business you admire to compete in 2026 via this link.
As mentioned in the episode, find Penn's JP Transport Youtube channel via this link. Hear more in this November episode of Overdrive Radio attendant to Penn's October Trucker of the Month nod:
[Related: John Penn reaps 10-mpg-plus rewards of two decades learning, growing]
