When veteran concert promoter Louis Messina weighs adding an act to Messina Touring Group’s impressive stable of superstar artists, his eyes aren’t focused on the stage. Instead, he’s intently surveying the concert audience. “I watch eyes and lips: eyes, if they’re really focusing on the artists, and lips, if they’re singing along and if they’re smiling,” he says. “When I see that happening, that’s when I know I need to be involved. It’s rare that you see artists that can do that and [aren’t] just going through the motions. You know they bring this unique connection.”

Messina knows that feeling well; he remembers first experiencing it at just 7 years old, when his father took him to see Elvis Presley in his hometown of New Orleans. “I’ve never forgotten that energy in that room,” Messina says. “It was a feeling that I’ve never had before, and I’ve carried it until today. When artists and an audience connect with each other, it’s magical.”

Seventy years later, Messina and his enviable roster have created plenty of magic together, too. The Messina Touring Group origin story began in 2001 with acts including his longtime client George Strait — and since then, each of the artists Messina exclusively promotes has been within one or two degrees of separation from the country legend (with the sole exception of The Lumineers). Taylor Swift, Kenny Chesney, Blake Shelton, Eric Church and Old Dominion all once opened for Strait; then Ed Sheeran and Shawn Mendes both opened for Swift.

Simply put, Messina says, without Strait “there wouldn’t be a Messina Touring Group.” But Messina’s own story started way earlier. His promoting career got off to a dubious start in New Orleans in 1972 when he sold out a Curtis Mayfield/B.B. King show — only to have the artists get stuck in Atlanta, unable to get to the gig. “I had 8,000 people trying to break the doors down to get their money back. The New Orleans riot squad had to come out,” he recalls. He learned a valuable lesson: “After I got over my depression, I had to go back into the ring. I got knocked down, but I didn’t get knocked out.”

After a tumultuous run in New Orleans, in 1975, Messina and his mentor and fellow promoter, Allen Becker, formed PACE Concerts in Houston. They introduced several new concepts into the live-event business, including touring multi-artist festivals such as the George Strait Country Festival and OzzFest, and were the first promoters to own outdoor sheds, starting with Nashville’s Starwood Amphitheater. Messina and Becker quickly realized they could reap the rewards of, as the late Becker used to say, the revenue from “popcorn, peanuts and parking” — and, in turn, greatly mitigate the financial risk of promoting concerts.

In 1997, Robert F.X. Sillerman bought PACE for $130 million as his SFX Entertainment consolidated the promotion business. In 2001, Messina launched Messina Touring Group, and in 2003, he partnered with AEG. His noncompete clause allowed him only to promote country acts, and he started with a passel that included Strait and Chesney, both of whom he still promotes. “Nobody else was paying attention to country acts back then,” Messina says. “What I did was take a little rock’n’roll mentality and brought it to Nashville; meaning I’m not going to do the same old same old.” He also gave each act its own dedicated team that they consistently work with from tour to tour.

On the fall day that Billboard speaks with the voluble Messina, now 77 and a father of six, he is at his desk in Austin. (Messina Touring Group’s 35 employees — 70% of whom are women — are spread between its Austin and Nashville offices.) “This is the time of the year where I’m busiest because I’m prepping for next year and the year after,” he says.

Still, he’s able to take a moment to look back. Last year was his company’s most successful yet, he says, with 2024 coming in second. Swift doesn’t report her concert totals to Billboard, but Billboard estimates her 2023 shows for The Eras Tour grossed $906.1 million (the tour will end Dec. 8). In 2024, Chesney completed his highest-grossing outing yet, according to Billboard Boxscore, with $159.5 million for the Sun Goes Down Tour, which ended in August. And Strait remains big business: His June 15 concert at Texas A&M’s Kyle Field set the all-time attendance record for a ticketed concert in the United States with 110,905 ticket-buying fans. “Everything’s clicking and so, you know, we’re happy,” Messina says.

But for Billboard’s 2024 Touring Executive of the Year, an artist’s potential career arc can’t be reduced to the success of any one tour.

“Louie isn’t a tour promoter. He’s an artist promoter… He’s a champion of not just the current tour he’s involved in with you, but your whole career,” says Church, who has worked with Messina for 12 years. “Louie always said to me, ‘You think your dreams are big, but you’ll never out-dream me.’ ”

Your father was a boxing promoter. Though you’ve said he didn’t influence you because your passion was music, what did you learn from him about taking risks?

I hate to say this because my dad’s passed away. He was a good man, but what I learned from him was what not to do. He was not a good businessperson. He did take me to see Elvis and exposed me to the excitement of what live music does. That’s what I’ve learned from my dad.

PACE pioneered the concept of touring artist festivals — multi-act events that would travel the country — but such stadium festivals are virtually gone now. Did local and regional festivals kill the touring artist festival?

I just ran out of talent. And the whole ego about “I’m not going to play in front of this guy… I need 110% billing… I need this. I need that” — it just wasn’t worth it. Then we started building amphitheaters and we made more money doing an amphitheater show than we did [promoting] stadium shows.

Two years into starting Messina Touring Group, you partnered with AEG. How does that relationship work?

I operate totally independent of AEG. Hell, a lot of times I’m competing with AEG over tours. They have their model, Live Nation has their model, and I have my model. My model is about careers, not tours. I always say I’m not in the rent-a-band business. I want to know what that artist’s vision is five and 10 years from now.

Legendary booking agent Wayne Forte unintentionally provided you with a light-bulb moment that changed your approach when you started Messina Touring Group. What did he say?

I was booking amphitheaters, and I referred to artists as inventory, and Wayne goes, “I’m sorry, Louis, did you just call artists inventory?” Literally, it stopped me in my tracks. I went, “I sure did.” At that moment, it totally reset my mind and where I was going in this business. I [wouldn’t] say I’d lost the passion, but I was a promoter that was just trying to sell popcorn and peanuts and parking. And I’m going, “This is not why I got in the business.” I got into the business because I love the passion of it. I changed my whole mentality at that point.

Most of your clients came from being opening acts for artists you were already promoting. Do you advise your acts on their openers?

With Kenny and George, I’m totally involved. Taylor always picks her opening acts. I’m involved with some and with others, I follow their lead. I believe there’s no such thing as overkill. Give the people their money’s worth. I’ve got George and Chris Stapleton and Little Big Town playing stadiums together and Zac Brown Band playing with Kenny. It’s magical.

The newest star in your orbit is Megan Moroney, who recently opened for Kenny Chesney even though you hadn’t seen her perform beforehand. Will she become your next client?

I’d love to work with her. I think she’s amazing. [Chesney’s manager] Clint [Higham] and I were talking about Kenny’s support and we brought up Megan Moroney. Kenny goes, “She’s only got one hit.” I go, “This album is so deep. Kenny, I’m telling you, this is going to work.” I’d never seen her perform, I just listened to her music and her songwriting. We put her on, and oh, my gosh, I’ve never seen Kenny so excited about an artist. He called me and he goes, “Louis, you were right. I was wrong.” But it didn’t take long for Kenny to recognize because Megan is such a natural star.

The production on Swift’s The Eras Tour is unlike anything that fans have seen. Has it changed what can be done onstage?

What Taylor has done is to me the best show I’ve ever seen. She amazes me night after night. She’s one of a kind. She’s always been like that. I’ve known her since she just turned 17… I always tell people, “You think you’re working? Go sit around Taylor for 15 minutes.” I remember when she was the first of three acts with Strait. She was the first one in the production office every day after visiting radio [stations], handwriting notes to people around the country. Ed’s the same way, Eric’s the same way, in their own way. None of the artists I work for is dialing anything in. They’re working their ass off.

The Ticketmaster site crashed when the Eras tickets went on sale, upsetting fans and leading to an antitrust suit against Live Nation and Ticketmaster. In hindsight, what could you have done differently?

When you have 15 million people trying to buy a million tickets, nothing could handle that. When we started adding shows, what [Swift’s management company] 13 and everybody decided to do was to stagger on-sales where instead of putting five shows up at once, we would put one show up at a time. Everybody’s blamed Ticketmaster, but I use this analogy: Imagine getting into a subway car in New York City. It holds 40 people, but 1,000 people are trying to get in that subway car. It just doesn’t work. They can’t get in. That’s what happened.

What’s the biggest change you’ve seen in negotiating artists’ fees over the last 10 years?

The biggest thing is [other promoters] playing with house money. These touring deals that some of my friends and competitors make, it’s ridiculous. The sales pitch [is] “What’s it going to take financially?” I don’t believe in that because if you’re tied to a check that somebody wrote to you, that means you have to play so many shows, your ticket price has to be this. You lose control of your own destiny. My trying to compete with a checkbook, that’s the hardest part I have because my sales pitch is “Let’s talk about the future. Let’s talk about your dreams.” Do what you’re supposed to do and the money will be there. If you chase the money, you’ll never get there.

Ed Sheeran has talked about trying to keep ticket prices low. Is there something other acts can learn from him?

No. This is one thing that’s wrong with artists that [want to price tickets too low]. Ed goes, “Louis, I want to go to bed at night knowing that this is the ticket price I wanted my fans to pay.” I go, “Ed, you’re beautiful for saying that, but here’s the problem: People are going to go to the secondary market and spend $700 on a ticket that you want to sell for $99… and you’re only going to get $99 of it.” I remember a long, long time ago working with George and his tickets were really reasonable and I did a printout of StubHub or whatever and said, “This is how much your tickets are being sold for right now.” And his eyes got big, and it was like a “Holy crap” moment for him. He had no idea.

Which acts are on your wish list?

I love Bruce Springsteen. I adore [Springsteen’s manager] Jon Landau and [tour manager] George Travis. They are all like family to me even though I don’t promote Bruce anymore these days because [Springsteen’s longtime agent] Barry Bell said I was too cheap, that I wouldn’t do the Bruce Springsteen deal. I don’t work at a discount price. My other fantasy [act] is Beyoncé. I adore her. Sometimes it’s cheaper to just buy a ticket than to get involved with the artists you love.

You spend a tremendous amount of time on the road. What’s your best travel tip?

My best travel tip I gave myself is I stopped drinking. This Christmas will be two years. I figured me and Jack Daniel’s had a good run together.

Any thoughts about retiring?

Seeing an artist go from an opening act to a stadium act and knowing that I had a little bit to do with it and walking into that sold-out stadium and seeing that energy… Wow! Why would I want to give that up? I’m the luckiest human being in the world.

Messina will receive Billboard’s inaugural Touring Titan honor at its Live Music Summit & Awards on Nov. 14.

This story appears in the Oct. 26, 2024, issue of Billboard.