Black Sheep Express owner-operator Sam Kelly is headquartered in Brandon, Mississippi, with three trucks and two employed drivers in addition to himself. The fleet's been leased for almost two years to CST Lines out of Green Bay, Wisconsin, hauling dedicated cheese for a CST customer West to California, with brokered loads on the often-triangulated return.
Depending on the season, Kelly and Black Sheep operators Bubba Rushing and Rodriguez Byrd might bounce California to Washington, then back across the country. Speaking in April, though, he noted, his multiple-pick reefer load of meat would take him and his 2023 Kenworth W9 out of the Golden State across to South Carolina for delivery.
He's not much into the short-haul work, that's sure.
"It’s risky, it’s a roll of the dice," he said. "I’ve learned my lessons about rolling the dice."
In more ways than one.
"The broker tells you your appointment’s at 9 but it’s really at 7," he offered as an example. "You get held up at a receiver and now you’ve lost a day."
Loads might pay better per-mile, but tight delivery windows mean extra opportunity for things to go wrong.
Lose time and "now how much was that short run worth?" Kelly said. "It can come back and backfire on you."
Sam Kelly
Adding to the difficulty: "The bottom fell out" of freight volumes and rates, he added, and he struggled through eight-nine months of payments on $180K brand-new trucks. He'll never forget "just saying, 'Hey, this is not working because you're paying for a truck one month out of your own money. I know there's going to be hard times, but you shouldn't have hard times every, single, month.'"
He got out from under the leases, and re-evaluated. And what's happened since is the story of a remarkable comeback, of a man committed to fulfilling promises made, to learning, and setting a team up for long-term success.
"We're not going to stay at three trucks forever," Kelly said. "I'm a man of big appetite, if that makes sense. So hopefully, you know, maybe I can fulfill it one day."
Sam Kelly, with his three-truck Black Sheep Express, gets the nod as Overdrive's Trucker of the Month for April, and this is his story.
Owner-operator Kelly joins fellow Truckers of the Month in competition for Overdrive's 2026 Trucker of the Year award. Nominations are open for exceptional owners, whether leased or independent (up to three trucks). Enter your own or another owner-operator business you admire via this link.
'Black Sheep' of the family makes good
Sam Kelly comes from a family of "doctors, lawyers," he said. "My granddaddy was a mayor. Not truck drivers." Hence the name of his company, in business upward of six years now.
He didn't set out as a young man to own trucks. He spent upward of a decade from age 18 working at a repair shop -- diesel pickups, one-ton duallies, autos -- first as a "go-grab-the-parts guy," he said, then service shop manager.
When a downturn came for that business and Kelly couldn't find work that paid up to par, he got to a place where money was so tight he couldn't afford the rent on his home. He found truck driving, starting with CRST, getting trained through the company's school and in a truck OTR after getting licensed. He was in that truck for "longer than I should have been" by the company's usual standards.
The money was decent, nonetheless, but when he finally got into a team-OTR operation with the potential to be more permanent, everything changed.
"Some weeks were OK," he noted, "some not."
[Related: Trucking self-dispatch: How to get comfortable and master the process]
Months into his work there he canvassed carriers around his home in Mississippi and found Amistad Freight in Union, where he would work for roughly seven-eight months, all the while socking money away with a singular goal in mind.
Between 2019 and all the way up to late 2021, Kelly effectively "lived in the truck, and saved up enough money to buy my first," he said.
Right in the middle of 2020 and the burgeoning freight market that would really take off the following year, Kelly's driver pay at the fleet was just "42 cents per mile," he said, yet he was able to keep saving, always with an eye out for better opportunities.
He took one early the next year with U.S. Freight Lines, headquartered in the Chicago area in Arlington Heights, Illinois.
"They're one of the good Chicago companies," Kelly said, invoking the stain left on the region's trucking community by outfits known for fleecing drivers and would-be owner-operators with terrible deals.
[Related: Super Ego accused of ELD cheating, stealing driver pay in '60 Minutes']
U.S. Freight Lines owner Victor Turcan started with one truck nearly 20 years ago, and since has grown the company to more than 100 wth a singular focus on service. When it comes to the many truck operators he's employed over those years, a very, very few fit that focus as well as Sam Kelly, he said.
"A true hustler, a guy that never, ever disappointed," Turcan said of the owner-operator. "Always on-time, and he did absolutely everything that he could to deliver the load."
Turcan truly means that absolutely everything, recalling a load across Wyoming headed West when Kelly was a company driver early on in his time with the fleet. He thinks it was a Sunday, Kelly in an effectively "brand-new Volvo," Turcan said, that had major engine problems inexplicably on I-80 around Cheyenne.
"What this guy [Kelly] does, he calls us and only says one thing: 'Get me a truck ready in Chicago,'" as Turcan told the story. Company personnel protested a bit, assuring him that he wasn't responsible for any re-power on his own, but Kelly was persistent. "'Get me a truck ready,' and that's it. 'I'll take care of the load,' he said."
As Turcan recalls, Sam Kelly took a bus to Denver, then a flight to Chicago Sunday evening, all on his own dime, and was back to the freight in time to deliver on schedule later in the week.
"He wasn’t responsible for all this, but that’s just the type of a guy he is," Turcan said. "When he said, 'I’ll be there,' he’ll be there, whatever it takes."
The hustle, the personal responsibility, keeping promises, all served him so well he eventually afforded a cash payment for a 2018 International ProStar in late 2021, even in the inflated used-truck market of that time.
[Related: Used-truck purchasing heating up: Pricing offers mixed signals in latest data]
A business trial-by-fire of sorts began, as Kelly leased the ProStar to U.S. Freight and almost immediately had copious mechanical difficulties.
"That truck was a nightmare," Kelly said, over his almost two years of ownership, despite just 300,000 miles on it at purchase. Emissions failures were "never-ending. I had a warranty on it," but the downtime was killing him.
"Insurance and other payments don't stop," he said.
He nonetheless made do, getting all he could out of the unit and making that initial move to a multi-truck fleet detailed up top. He would go on to trade the ProStar in for an ultimately more reliable 2022 International LT that would also serve as his vehicle toward a business reboot now taking him and the team forward to further growth potential.
Problem-solver solves the problem -- Black Sheep's big comeback
Sam Kelly utilizes Victor Turcan and company's truck-and-reefer-trailer-focused Xpress Shop in East Dundee, Illinois, for maintenance to this day.
"I run my trucks through their shop about once a month, if not once every six weeks," reefer trailers too, he said. Major breakdowns are handled at a dealer shop, as all trucks remain under warranty.
Yet his three-truck fleet is no longer leased to U.S. Freight. He came to Green Bay, Wisconsin-headquartered CST Lines in June of 2024 after seeing its self-dispatch program advertised on social networks with "no cargo, no liability insurance" deductions and still a high 87% of the linehaul rate with your own trailer, he said.
CST Logistics Manager Karla Linssen handles the company's direct-customer freight, and since early in 2025, Sam Kelly and Black Sheep's drivers have been on outbound cheese runs from Wisconsin across the country regularly.
"I'm impressed with Sam," Linssen said. Working with owner-operators and drivers over her 22 years with CST, "you get different capabilities. He's got great communication. Some drivers are late and they don’t tell you. Not with Sam. If there is a problem, it’s communicated."
Kelly's surrounded himself with similarly capable operators in Rushing and Byrd, too, who work directly with Linssen on those outbound-to-Cali loads, too.
Bubba Rushing is pictured with the '22 Western Star Kelly bought early this year.
He purchased his first reefer -- from Pedigree Truck Sales in Springfield, Missouri, with a very-new refrigeration unit on an older chassis/van -- to get the extra 10% CST offers contractors who own their trailers (he's since bought two more). By April of last year he could see the potential if he ran it team, ensuring more dedicated outbound freight and easing regulatory time pressure on the return, otherwise always necessitating a solo restart built in somewhere on the journey.
Kelly's longtime Mississippi-local friend, Rodriguez Byrd, joined him in the International, where the pair set about cementing the return of Kelly's Black Sheep Express, the relationship with Linssen and CST on that dedicated freight, profits in an otherwise tough year .... and, perhaps most importantly, a "friendship of a lifetime," Kelly said. "We didn't do anything fancy. We didn't slow down. We stayed consistent and kept pushing," with brokered freight on the return.
Rodriguez Byrd pilots this 2023 International LoneStar.
"You have to give that broker every reason why you are the better option" than the fly-by-night competition out there, he said.
It's working. Revenues, profits building, by the end of 2025 he'd parked the 2022 International LT as a backup and taken advantage of deals in the used market for two lower-miles tractors, then a third this year.
Picture are (right) the 2023 Kenworth W900 owner-operator Sam Kelly drives today, the 2023 International Lonestar piloted by Byrd, and Rushing's 2022 Western Star. Both company drivers are paid 65 cents/mile.
As noted up top, Kelly and team are following the freight and adjusting legs for brokered triangles on the turn back from California to be in Wisconsin. Now with three units and operators running, ensuring a truck's back for the dedicated freight feels logistically simpler for him.
Owner-operator Sam Kelly's well-prepped for what looks like a general freight market turn ongoing. And the problem-solver in Kelly is always at work, crucial for any business owner and a standout quality in his outlook, according to CST's Linssen.
"He keeps good relationships," she said, describing a load he was under headed West for CST. "Something happened and he couldn’t pick it up" at the scheduled time the next morning. As Linssen tells the story, "He said, 'My former operations manager -- they run West. I'll give him your name and number.'"
Linssen ended up outsourcing that particular run through CST's brokerage to the carrier. Sam Kelly "gave me a lead, and since then, this carrier has handled many loads for us," Linssen said. "They’re a solid backup for us."
Echoing Victor Turcan of U.S. Freight, Linssen notes that sense of obligation to help remedy the situation by a leased owner-operator leaves a huge impression. "That has never happened before in all my years" in trucking, since she was first out of college decades gone by, she said.
[Related: Minding the Ps and Qs of costs, rates: Trucker of the Month Greg Labosky]
