How The Pollstar Live! Conference Helped Walla Walla (Pop. 33,714) Land A Jelly Roll Show

No matter how you remember it, Scott Daggatt did not ask Jelly Roll to tour Walla Walla, Washington, a town of fewer than 35,000 people in the heart of Washington’s wine country, 210 miles southeast of Seattle.

It was April 17, 2025, at Pollstar Live! where Jelly was wrapping up a free-wheeling conversation with Live Nation CEO Michael Rapino in one of the best attended panels of the annual conference. Near the end, Daggatt stuck up his finger to ask a question.

“I wanted to make a comment, and it really had to do with his connection with his fans. But before I said anything, I said, my name is Scott Daggatt. I’m from Walla Walla, Washington and I have Wine Country Amphitheater, which is too small capacity for where you’re on your career right now. But I want to to make a comment about your connection with your fans and ticket brokers and scalpers,” Daggatt tells Pollstar.

And from there, there was a colloquy about how bots and scalpers drive up ticket prices and what that means to Jelly Roll specifically, because much of his rise was fueled by a core group of fans called the “Bad Apples,” who often faced the struggles Jelly did — financial strain, incarceration, instability — and are frequently not in major coastal cities and for whom secondary-market-inflated prices are not a reasonable expense. It was a thoughtful discussion, with blame laid on bots and scalpers.

“Then at the end, he’s kind of done, but then he looks at me and he goes, ‘Don’t leave Walla Walla out. I promise you, I will play Walla Walla in the next 36 months,” Daggatt recalls. “I can see Michael Rapino’s eyes kind of go up.”

Jelly was directing his instruction — “Don’t leave Walla Walla out” — to his agent, CAA’s Hunter Williams, and manager John Meneilly, who were sitting a few rows behind Daggatt.

So Daggatt turns around and hands Williams his card, explaining how to route a tour to his little amphitheater — really just a rented stage in front of a picturesque field of waving wheat at the bottom of a slight slope.

“Forget about Jelly, it’s hard to get shows here at all,” Daggatt says. “I’m not trying to pick on Live Nation, but Live Nation is in Spokane and Boise and we’re the new kids of the block.”

Which isn’t to say Daggatt hasn’t had success, with shows from Jackson Browne, Norah Jones, Bonnie Raitt and Alison Krauss & Union Station in recent years, which reads as the kind of acts a venue surrounded by 125 wineries might book. Jelly Roll is…different.

But obviously the prospect lodged in his mind, unlikely as though it may seem. Daggatt’s no naive newcomer — he earned his bones at Management III and Concerts West with Jerry Weintraub, the godfather of modern touring — but he’s a determined businessman too. So seven months later — a few months after Jelly wrapped the “Big Ass Stadium Tour” with Post Malone, which finished at No. 10 on Pollstar‘s year-end touring chart — Daggatt emailed Williams.

“I got an email a little bit later that just said, ‘You never know, the stars may align,'” Daggatt says. “And so I thought, OK, that’s positive. That’s not a no. After all, Jelly did say within three years.”

More time passes, another month, and Daggatt follows up with a phone call. Williams says he was routing tours for Jelly and others but it was still too early to talk about Walla Walla, and Daggatt took it in stride. This is, after all, a major artist who just came off a huge stadium tour and Williams thought enough of the idea to get on the phone with him.

The holidays come and go, the year turns over. Suddenly, it’s early February. Jelly and Post Malone have announced a second run of the tour and Daggatt figures he might as well call Williams, just to stay on his radar, just to say no hard feelings if it couldn’t get done this time. So Daggatt rings the CAA Nashville office again, Williams’ assistant says his boss isn’t there, but he takes down Daggatt’s number.

“So at 6 o’clock that night, I’m eating my dinner here in Walla Walla, watching a K-drama or something, who knows, and Hunter calls and says ‘Why don’t you call me, we might able to work something out.’ He says ‘Call me as soon as you wake up tomorrow,'” Daggatt says. So naturally, of course, Daggatt did. At 6 a.m. Pacific (8 for Williams in Music City).

And the conversation is about a lot of specifics: security, catering, operating expenses. All the kinds of details an agent and promoter hammer out when a deal is final, or close to it.

And there was the matter of the guarantee.

“He says, ‘I’ll make this real simple. We’ll take 100% of the ticket sales. You take the bar,'” Daggatt says. “And I said ‘God, thank you.'”

There’s back and forth about the stage — for most shows, Wine Country Amphitheater rents a $12,000 stage; Jelly has a 13-member band and, no offense to the guy who wrote “Running On Empty,” but quite a bit more of an elaborate production than Jackson Browne. Williams said they’d need a stage that’s closer to $85,000.

But all this discussion…suddenly Daggatt can’t help but think this is real. They hang up, Williams understandably has to run this by Live Nation, but finally he tells Daggatt, “Relax, have a good weekend and call me Tuesday.”

The tour — eventually it’s branded as the “Little Ass Shed Tour” and has stops at various east coast and southern amps, and, surely by now you know, one in the Pacific Northwest — will be announced Feb. 23, a week after President’s Day, but over the long weekend, if only just briefly, a mention of the July 22 stop is made on Jelly’s Instagram. It’s only up for a half hour, but long enough for someone in Walla Walla to screenshot it and post it to various local Facebook groups. Word gets around fast in a town of less than 35,000.

“And everyone’s saying ,’Oh, that’s fake news,'” Daggatt said. “The only one who believes it is me.”

Of course, Williams confirms the date with Daggatt the day after President’s Day and now the small town promoter has to keep his mouth shut about what he told Williams was “the worst-kept secret in Walla Walla.”

It was front-page news. At the on-sale, 5,600 tickets were gone in less than two minutes (Daggatt did hold back some tickets to ensure locals would have a chance, plus Jelly Roll likes to have freebies available for people transitioning out of incarceration or rehab; total attendance will be 6,000).

“The town is upside down on this whole thing. They’re calling it the best thing that’s ever happened in Walla Walla. I have people coming up to me that I don’t even know. I work out the YMCA, I do my workouts. I spend a lot of time here at my home office but now, all of a sudden, everybody seems to know who I am. This is like, this is my 15 minutes of fame, you know? So that’s been fun,” he says.

In the meantime, he’s learned that, common with many artists, a big part of being on Jelly Roll’s team is managing his ideas, discussing with him what is or is not a doable venture. But for whatever reason, Jelly was insistent on playing Walla Walla.

Maybe he believes in keeping his promises — a very public one at that. Maybe he likes the name “Walla Walla” (it is fun to say). Or maybe he knows that the Washington State Penitentiary is there.

In a business that’s increasingly corporate with routing based on a deep analytics, it’s good to remember that there’s still a place for hard work, dogged determination and good old fashioned luck.