Billy Strings Recalls Losing $1,000 to Willie Nelson in a Poker Game That Ended “Real Quick” ML

Willie Nelson is a card shark, and Billy Strings learned that firsthand.

The one cool thing about the country music genre is that the legends are often more than willing to help out the up-and-comers. Advice is plentiful, guidance is readily available, and card games are ruthless. That’s at least how things played out when Billy Strings sat down to play poker with Willie Nelson.

Strings was a guest on The Howard Stern Show recently and explained that he’s been fortunate enough to share time with the Red-Headed Stranger on numerous occasions. One of those times happened to be a decades-old card game with Willie and some of his closest, oldest friends.

And thought the table was surrounded by friends – and an in-awe Billy Strings – Nelson didn’t take it easy on the young, bluegrass country artist:

“I’ve been really lucky to spend a little bit of time with him. (I haven’t smoked with him). Willie might be taking it easy now. He takes a lot of edibles and stuff. We did play some cards. He took $1,000 bucks from me real quick.”

Notice that he said he took $1,000 from him “real quick.” To me, that leaves the door open for even more losses for Billy (and more winnings for Willie). For Billy’s sake, hopefully there was a $1,000 buy-in and that’s all he could lose.

Strings says that Willie’s wife judged her living legend husband for taking money from the 33-year-old, but that Nelson insisted that Billy brought the financial loss upon himself:

“I don’t really know how to play, but I sat down anyways. That’s the thing too. His wife, Annie, was going, ‘This is disgusting. The boy doesn’t even know how to play.’ And Willie’s like, ‘Well he sat down, didn’t he?’ I’d spend another $1,000 to sit down and bulls*** with those guys.

Willie and his buddy, Steve, I said, ‘Man, how long have you all been sitting here playing cards?’ Steve says, ’50 years.’ Listening to those two bulls** each other and talk s*** and tell jokes, that was the highlight of my life. I was sitting right where Johnny Cash and Kris Kristofferson played cards.”

Glad to hear that Billy Strings basically just viewed the $1,000 as a cover charge to hang out with Willie and friends.

And though Billy Strings might have lost out on some money, he gained something that could be considered priceless. The “Dust in a Baggie” singer also shared that he got to play Willie’s iconic guitar, Trigger, and that there’s even a recording from that very night that’s in his possession:

“Before we got going (playing cards), Trigger was sitting there, and I was sitting there talking to Willie. I asked him, ‘Could I pluck a note on it?’ He said, ‘Yeah, go ahead.’ It was plugged into his old amp and stuff too, and the engineer in the studio hit record, and whatever I was playing on Trigger… I think I played a little Black Mountain Rag. The engineer recorded it, so somewhere I have a recording of me playing ‘Black Mountain Rag’ on Trigger.”

Lost $1,000, but gained a Trigger recording. I’d say Billy Strings would take that deal any day of the week.