Inside Derek Trucks’ Whiskey Distilling Journey

Back in what he calls “the Winnebago days,” when he was touring with his solo band, Derek Trucks had one fan he always loved to see. “There was a guy who used to come out to our shows in Kentucky and just bring incredible stuff that we didn’t know about down here,” says the guitarist, half-namesake of the Jacksonville-based Tedeschi Trucks Band, the Southern rock powerhouse he leads with his wife, guitarist Susan Tedeschi. And by stuff, he means bourbon, which, as he was barely legal drinking age (if that) at the time, Trucks didn’t know too much about other than he liked to drink it.

“It was George T. Stagg, and early Pappies,” Trucks says, referencing the prized and legendary Pappy Van Winkle whiskey, bottles more elusive than he knew. “We were drinking it like idiots.” A year later, back on another tour, Trucks and his bandmates would ask their friend for more of the same. “And he’s like, ‘Yeah, it’s not really that easy to get.’ That was the first time I was tipped off to the really high-end bourbon.”

Thus began a beautiful obsession. As he spent big chunks of time on the road, Trucks had frequent occasion to check out “old, dusty shops” off the beaten track where he could score overlooked rarities at bargain prices. Eventually, he’d join his brother David and their friends on an annual trip to Kentucky, where they would pay a barrel-picking visit to the Buffalo Trace distillery in Franklin County.

“It was that one time of year when we would all get together and get away from the world a little bit,” says the performer, who hopped on a recent Zoom video call from the “record spin and bourbon room” of his Jacksonville home, its shelves lined with bottles of fancy whiskey, vinyl LPs and multiple Grammy Awards. “It became the highlight of the year.”

Now the musician has found a way to share that experience, and his finely tuned taste in bourbon, as the purveyor of Ass Pocket Whiskey. The current release, named “The Search,” is a 10-year-old Kentucky Straight Bourbon from 18 barrels hand-selected by Trucks at their Bluegrass State source. “The undisclosed origin adds to the mystery—a thrilling aspect every bourbon lover appreciates,” noted one reviewer on a Reddit discussion thread. The libation is bottled in a 200ml flask—not quite a half-pint—which easily fits into a back pocket or perhaps more handily an inside jacket pocket. But, somehow, Jacket Pocket Whiskey doesn’t have the same ring.

“It’s been so fun to have this extremely high-quality liquid in a precious industry, in this really unpretentious vessel with this extremely self-aware brand energy, right on its sleeve,” says Casey McGrath, who partnered with Trucks and his brother to co-found and create APW. A man who wears many hats, McGrath also is the co-founder and creator of Four Walls Irish American Whiskey with actors Rob Mac, Charlie Day and Glenn Howerton of the Hulu comedy “It’s Always Sunny in Philadelphia,” and the creative director and manager of Kings of Leon. The Tennessee rock band also has its own brand, Kiamichi Whiskey, a collaboration with the fabled Willet Distillery. But APW has its own distinct vibe. “We have it in this really fun thing to pass around,” McGrath says, “and drink it right out of the bottle.”

The name comes steeped in its own lore: It’s inspired by the 1996 album “A Ass Pocket of Whiskey,” which paired North Mississippi bluesman R.L. Burnside with the scuzzed-out rock trio Jon Spencer Blues Explosion. If you’ve spent a raucous night in a Hill Country juke joint, enjoying a raw, seditious groove that never quits, taking pulls from a shared bottle of moonshine, you’ll recognize a kinship. Crack the seal and take a sip. At 107 proof, the whiskey kicks like a mule but then becomes satisfyingly refined.

The blues allusion makes sense. A guitar prodigy by the age of 13, Trucks was leading his own blues-rock band, and later joined the legendary Allman Brothers Band, playing alongside his uncle, founding member and drummer Butch Trucks. Few contemporary guitarists are as steeped in the tradition, or play a slide with such searing improvisatory passion. Culturally, it’s a sure bet.

“Being from the Deep South, there’s a conflicted history,” Trucks says. “I mean, there’s not a lot of stuff you can just truly be 100% proud of. But this is one of the things: You can be way into the Allman Brothers and bourbon. There’s something about it that just feels good. “

Of course, he’s hardly the first rock’n’roller to have his name attached to a liquor brand. Bob Dylan has Heaven’s Door whiskey and Willie Nelson has Whiskey River—both named after the artists’ classic songs. APW’s partners don’t consider theirs a celebrity brand, however. “It stands very much on its own conceptually,” McGrath says. “You shouldn’t be afraid to open up a bottle of whiskey because what’s inside is too good.”

Or, as Trucks says, “It’s about the juice first.”

He recalls a fateful night, right after he and David had made their first barrel pick, when they had a cookout with Ed James, part of the APW team whose father-in-law happens to be Julian Van Winkle III—the third generation of the fabled family of distillers. “Julian was there,” Trucks says. “He had this beautiful bottle made for me and my brother—it was the Trucks family barrel pick. It was a 10-year-old Pappy. This kind of Holy Grail thing. I was like, ‘Is it rude if I just crack this thing, we drink it here?’ Julian was like, ‘No that’s what you’re supposed to do.’” The realization hit him. “When is going to be a better time than now, with this incredible collection of humans? This is a good night for it.”

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