How a drug bust in Wythe County pushed Charley Crockett into a country music career

Robert Hafley liked to eat lunch in his patrol car.

The other state troopers in Wythe County that August day 10 years ago went to a Subway in Wytheville; Hafley pulled into the median along Interstate 81 near Exit 72 and chowed down on a baloney sandwich.

His eye spotted a car with illegal window tint headed north. Bingo. Hafley pulled out and turned on the flashing blues.

The driver was a 30-year-old man from Texas with a fedora perched on his head and a gold chain around his neck. The man was quite polite, but the car smelled of marijuana. Today, that wouldn’t have made a difference. When Virginia legalized personal possession of small amounts of cannabis in 2021, it removed the smell of pot as a probable cause reason to search a vehicle. But that law was still seven years in the future on this day in 2014. Hafley had sufficient reason to search the vehicle. He called for backup, standard protocol for a vehicle search.

The other troopers in Wythe weren’t happy with him at the time, Hafley recalls. They’d just sat down to lunch. He told them they’d have to pack up their subs and bring them along. The search couldn’t wait.

The troopers popped open the trunk. The first thing they saw was a guitar. The driver — whose home address was in Irving, Texas, just outside Dallas — said he had left Nashville and was on his way to try to score a record deal. The driver asked if he could have it. Hafley saw no harm in that, so he handed over the instrument. The driver sat on the grass bank strumming the six-string and singing a song. Hafley says he remembers this clearly because “it was just funny, I’d never had anybody playing the guitar while searching.” When the troopers pulled out a suitcase, the guitar-playing driver “immediately” switched to Willie Nelson’s “The Party’s Over,” Hafley recalls. That was the first sign that troopers were onto something.

“We unzip the suitcase; it has 6 pounds of marijuana,” Hafley says — actually 6.6 pounds, to be precise. The threshold for a marijuana trafficking charge — a felony — in Virginia is 5 pounds. “Now it makes sense why he changed the song,” Hafley says. This much pot would bring two felony charges, one for distribution, another for transportation.

Hafley took the driver off to the New River Valley Regional Jail. At the magistrate’s office, the driver tried to explain that the suitcase full of marijuana was “medicine” and that he had a medical prescription for the weed. The magistrate was skeptical. “Six pounds?” he asked incredulously.

Hafley remembers the driver’s response: “He just kind of dropped his head at that point.”

Unlike some suspects, the Texas man was unfailingly polite throughout the process. “He was good during the whole stop,” Hafley says. “He was obviously nervous and scared of what would happen, but he was never rude. He was respectful.” Hafley says the man was “a good sport about it,” so much so that “when I pulled away from the jail, I thought ‘I hate that happened to him.’”

With that, one Matthew Charles Crockett entered the Virginia criminal justice system with two felony counts and possible prison time hanging over him. At the time, he was a nobody, just another unlucky pot dealer with a colorful tale. Today, he’s better known as Charley Crockett, a breakout country music star with 15 albums to his credit, and that 2014 bust on the interstate figures in one of his newest songs, “Good At Losing,” an autobiographical account of his life before he became famous.

The key verse for us:

Lawmen they caught me in Virginia
No need to tell you what I done
Make sure you get your act together
Before you roll up 81

Actually, Crockett has talked quite a bit about the case in interviews, although few of those stories (mostly in the music press) have said his famous arrest took place in Virginia, and none say it happened in Wythe County. The court case that followed was pivotal to Crockett’s subsequent music career because, had it gone a different way, that music career may never have happened. The maximum sentence for the sale, manufacture or trafficking of more than 5 pounds of marijuana is 30 years in prison. In theory, Crockett could be sitting in a cell in Red Onion State Prison and not striding stages across the country (including recently at FloydFest).

Crockett’s representatives didn’t respond to Cardinal, but in an interview last year with Texas Monthly , Crockett gave a fairly extensive account of his marijuana-dealing exploits. He’d grown up in Texas and drifted all over the country and around the world, even spending time in France, Spain and Morocco — he has a colorful biography of playing on street corners and riding in boxcars. Eventually, Crockett wound up in California, working on a cannabis farm in Mendocino County and looking for a way to self-fund the album he wanted to record. Farm work wasn’t going to cut it, but selling weed would. He told Texas Monthly he’d only started selling marijuana about a month before his Wythe County arrest and quickly found out how easy it was to make money. He pocketed $1,500 from a simple two-hour drive to San Francisco. “That was a lot of money, and it was thrilling,” he told Texas Monthly. “But there was a lot of fear, driving with all that in your trunk. I didn’t even have a license. I was living so far outside society that I forgot myself. I forgot the risk.”

A state trooper in Virginia who happened to prefer a baloney sandwich in his car to lunch at Subway reminded him of that risk.

Crockett gave a more dramatic account of the Wythe County stop than the one Hafley told:

“ They pulled me out of the car … and I knew I was going to jail,” he said. “They were making fun of me, these cops.” When they asked where he was headed, Charley said he was en route to a gig. The law didn’t buy it. “They were like, ‘Yeah, boy, you’re a country music singer. I’ll bet you are. Why don’t you play something for us right now?’ ” He grabbed his Telecaster — and froze. “I pulled out that guitar, nervous as hell, and I swear to God the only song I could think to play was [Willie’s] ‘The Party’s Over’ ” — he strummed an air guitar and started singing, “Turn out the lights, the party’s over”—“and they were like, ‘That’s a fitting song, boy.’ Then that dude busted the suitcase open and [found] a bunch of medicinal plants.”

In that Texas Monthly interview, Crockett said he had funded the cross-country trip by selling weed — he’d left California with 50 pounds. “That was his plan to fund his first record, running dope to cities where he’d busked,” Texas Monthly reported. That matches what Hafley recalls Crockett telling him: “He actually had more than that when he started. I think that’s how he was paying his way to New York.”

Crockett wound up spending about a month at the New River Valley Jail until he was released on bond. Austin Monthly says he spent that time doing some hard thinking and realized he needed to get more serious about his music career. He walked out of the jail convinced that the only way out of his drug charges was to establish himself in the music industry and hope that would earn him some leniency. He went back to California and recorded his first album — ironically, in a cabin at a cannabis farm . In an interview posted on the Sunset Sound recording studio site, he told an interviewer: “Had I not gotten busted, I’m sure I wouldn’t have made ‘Stolen Jewel.’ I would have probably kept going and gotten in a whole lot more trouble than I did … So getting busted made me take recording more serious.”

It was March 2016 — three months shy of two years since his arrest — that Crockett was finally sentenced. By the time he appeared before Circuit Court Judge Josiah Showalter, he’d been busy. His first album, “A Stolen Jewel,” was something he did on his own, without the benefit of a record label. He paid for 5,000 compact disc copies, which he then set out to sell at as many shows as he could book. He played lots of shows, landing gigs as an opening act for the Samantha Fish, Lucero, the Old 97s, Shinyribs and the Turnpike Troubadours, a who’s who of acts that weave back and forth between the lines of country and the blues, both genres that Crockett makes use of. That record won him some acclaim — the Dallas Observer Music Awards named Crockett the Best Blues Act. He landed a deal with an actual record label, Field Day Records, a small but respected indie label in Dallas. He had a new album, “In the Night,” nearly finished, with more shows lined up. He also had a big-name attorney: Jimmy Turk of Radford, whose reputation stands tall in Southwest Virginia courtrooms. Some of the legal proceedings were handled by one of the other attorneys in Turk’s firm at the time, Naomi Huntington, who later went on to serve on the Radford City Council. (She referred all comments on the case to Turk, who did not respond to multiple inquiries.)

Crockett pleaded guilty to the distribution charge; the transportation charge was “nolle prosqui,” legal language for it simply went away. Crockett was given a 10-year suspended sentence and fined $10,000. Other than having to check in with a probation officer, Crockett was free to go.

Some accounts in the music press say that Crockett sent the judge a copy of “A Stolen Jewel,” and the judge was so impressed he gave Crockett a break to spare him from prison. The Austin Monthly credits Crockett’s “disarming megawatt smile” and the CD with winning the judge over. That may be somewhat embellished. David Saliba, who prosecuted the case and is now in private practice in Harrisonburg, says for one thing it’s well-known in court circles that Judge Showalter doesn’t like country music. For another, Saliba says the eventual sentence is fairly standard for that type of marijuana charge. “It wasn’t meth, it wasn’t Oxycontin,” Saliba says. “I don’t think he had any prior record. It was on the lower end of a lot of those interstate cases. They pull U-Hauls over every now and then that are loaded up.”

Whether Crockett actually sent his record to the judge as some accounts claim i s unclear — the judge did not respond to a Cardinal News inquiry; judges typically don’t comment on the cases they’ve handled. However, Saliba does remember a CD being mentioned or shown in court, along with Crockett’s need to be able to travel to pursue his career, but otherwise, his memory of the case is hazy. It just didn’t make that much of an impression at the time. There are lots of drug cases off the interstate. Neither Saliba the prosecutor nor Hafley the state trooper made the connection between that case a decade ago and Crockett’s current fame until Cardinal contacted them.

Crockett’s own account is fairly straightforward: “I showed him I’d made strides over the two years it took to get to trial,” he told Texas Monthly. He told the Sunset Sound interviewer that the judge “saw I had something else I was doing and not just paying ’em lip service and wasn’t going to be right back into it — relapse.” Whether routine or not, the lack of a prison sentence allowed Crockett to continue his music career. He’s since racked up a bunch of honors — and when his new album, “$10 Cowboy,” came out earlier this year, he was back in the New York that he’d been headed to that day in 2014. Except this time, instead of busking on the street, he was playing on “Jimmy Kimmel Live.” Crockett’s drug arrest in Wythe County may have given him a good verse in “Good at Losing,” but right now, he seems pretty good at winning.

See also: “We need more stories about Interstate 81.”

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