"After I left Clear Channel, I said I only wanted to work for artists that want to work with me," says Messina, 67. "And the artists that want to work with me, I'd kill for them." It's a relationship that has paid off handsomely for all involved. So far in 2015, Messina's 155 shows have grossed nearly $290 million and sold almost 3.3 million tickets, according to Billboard Boxscore -- Swift alone accounts for $152.6 million from her first 50 shows (the U.S. leg wraps in Tampa, Fla., on Halloween night), and Church hit the 500,000-ticket mark on his first-ever arena tour.
Now based in Austin with his 21 -- person staff, the married father of six caught up with Billboard from Sin City, minutes after a press conference wrapped announcing Strait's upcoming engagement at the city's new Las Vegas Arena.
Is Strait's forthcoming stint in Las Vegas a residency?
I wouldn't call it a residency; George is doing an exclusive worldwide engagement. We announced a couple of weekends [April 22-23 and Sept. 9-10, 2016] and we'll see how it goes. George said he still wants to play shows but he's not going to tour, so we thought this was the perfect thing to do: play a new arena and be part of the grand opening. Vegas is such a destination town -- George Strait can be the destination. I joked with him, "You're not going on tour, but we're putting your fans on tour."
How is promoting Taylor Swift as a pop artist different from promoting her as a country act?
The principles stay the same, the bar just gets higher and higher. Taylor always has been Taylor. She started out in the country format, but she never has been the girl with the straw hat on: There's country, there's pop, and there's Taylor Swift. Now, when she plays early stuff live, it could be on , and half the stuff on that album, if she wanted to put a twang in it, it could be on a country album. Kenny does wear a straw hat and is also a rock 'n' roll show, and so is Eric. When I first started doing country music, my whole idea was to take a rock 'n' roll mentality to Nashville: filling stadiums with George Strait, doing things differently.
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Taylor has had many special guests on her tour -- who coordinates that?
Taylor does everything -- she's got a team, but she's the one making the phone calls. I don't even know who's playing -- "Oh, really? They're here?" She's a walking sizzle reel.
Church made a pretty significant step up with his Outsiders arena tour and its elaborate set. What was your first reaction to it?
When I first saw the stage, it was in the round, and I was like, "Are you crazy?" Now I'm like, "What do you want to do, Eric?" The artists I work with are all individuals, and I guess I'm just smart enough to follow their lead. I wish I could take some credit.
Chesney just finished his biggest tour yet -- $114 million in gross, 1.3 million in attendance -- which is unusual for a stadium-level veteran. How do you explain it?
Kenny has created this traveling event -- he built the "No Shoes Nation." He created a brand that his fans follow, and we always give his fans a great show. Look who we had [support acts included Church, Jason Aldean and Brantley Gilbert]. Kenny doesn't mind sharing the spotlight, because at the end of the night, it's his spotlight.
How is your relationship with AEG?
Great. I'm partners with them, but I work for the artists. I also do a lot of shows with Live Nation. I don't want to think anybody's my competition, because I'm going to do the best for the artists I work for. I am semi-independent, but I have a relationship with AEG where we're co-promoters on everything I do.
With so many acts on the road, how do you decide which show or tour to be on?
Let's just say I've got a lot of [frequent flier] miles. Eric started his tour in August of last year, and I'm sure I haven't had five weekends off since. This is the most I've traveled in my life. There were days at PACE when I was a "turn the page" promoter, because I had so many shows in the amphitheaters I didn't know who I was promoting. But [in 2015], having four major tours out, pretty much at the same time -- my routing looked like windshield wipers: one side of the country one day, the other side the next. But I try to cover as many shows as possible, because I still believe I'm the promoter. I work for them; if they're there, I feel like I should be there, too.
Even with a strong team in place?
I'm a believer in empowerment: The night of the show, I turn the keys over to whoever's show it is:Bridget [Bauer] with Eric and George, Rome [McMahon] and Kate [McMahon] with Kenny, [Mike]Dugan with Taylor, my son [Louis Messina Jr.] with Ed. But if they need me to smack somebody around, that's what I'll do. I'll give you a good analogy: I'm a relief pitcher. My bus is the bullpen. And if somebody needs me to throw strikes, I'm there. But mostly, I'm there for entertainment value. I really don't have anything to do the night of the show, to be honest with you. (Laughs.)
A version of this article was first published in the Oct. 17 issue of Billboard.