Meet the ‘Unflappable’ Exec Bringing Superstars To Madison Square Garden and Sphere
Billboard ·
MSG Entertainment president and Billboard 's Touring Executive of the Year Josephine Vaccarello has built relationships that translate into history-making runs at the company's venues.
On her first day of work at New York’s Radio City Music Hall in 1998, Josephine Vaccarello — just a month out of college, starting a job as an administrative assistant — left the building in the evening and had to use the after-hours exit. That required walking through the opulent theater itself, and she wasn’t about to waste the moment.
“I was like, ‘I’m standing on the stage of Radio City Music Hall. I’m just going to do a thing!’ ” Vaccarello recalls today. So the self-professed “theater kid” from Long Island launched into “On My Own,” Éponine’s iconic lament from Les Misérables . “I had to go for it,” she says with a proud grin.
Nearly 30 years later, Vaccarello is sitting high above Midtown Manhattan on the roof of 2 Penn next to Madison Square Garden, which bought Radio City six months after she started that job. She’s in a very different position: In September, after three years as executive vp, live of Madison Square Garden Entertainment (MSGE) — where she’s spent her entire career — she was named its president.
“I’m going to be honest: I never wanted to leave,” Vaccarello, 50, says of her time with the company. “I love the company I work for. I love the buildings I get to work in. It still makes me get excited when I stand inside any of the venues and watch an entire room of people singing every word to every song, and I’m like, ‘I get to be part of that.’ It’s cool.”
Since the promotion, she hasn’t exactly kicked back to celebrate: The week we speak took her to Sphere in Las Vegas, where she oversees residencies, for Metallica’s opening; the Garden for a New York Rangers hockey game and two Harry Styles shows, part of his historic 30-night Together, Together residency; and the 30 Rock cast reunion at Radio City, back where it all started.
Banner years may be business as usual at this point for both Sphere and the Garden, but even by those standards, 2026 was exceptional for both. The singular Las Vegas venue, in its third full year of operation, diversified its artist bookings with acts ranging from Carín León to No Doubt. The arena’s year was led by three monumental events: the New York Knicks’ NBA championship win; Styles’ residency; and a certain wedding of music and sports royalty (though of Taylor Swift and Travis Kelce’s nuptials, even Vaccarello can only say with a smile, “It occurred. It happened”). And this past summer was the biggest in the Garden’s history, with 57 shows (including multinight runs from Rush and Bon Jovi) compared with the previous year’s 36.
The list of what now falls under Vaccarello’s purview at the Garden is almost comically long — concerts, comedy, family entertainment, performing arts productions, Radio City’s Christmas Spectacular , sports properties, ticketing, suites and hospitality, and marketing campaigns — but she’s spent her life preparing to take it on. After graduating from the State University of New York at Albany with a degree in communications (presciently specializing in interpersonal communications and high-speed management), Vaccarello made it her business at Radio City to learn about every job around her.
“I’m inquisitive by nature — I need to know what it is, how it works, how you do it,” she explains. “The biggest thing for me was just raising a hand, like, ‘Oh, you need help? I’ll do it.’ ”
“She always stood out as someone who had a grasp of the entire business, whether it was how to time an on-sale or which building to play or which nights,” says Full Stop Management chairman Irving Azoff, who recalls first meeting Vaccarello when she was a junior booker, and who represents three of the first four acts to play Sphere (U2, Eagles and John Mayer, as part of Dead & Company). “It wasn’t ever just, ‘Yeah, the date’s available, do you want it?’ She always showed great enthusiasm for the process.”
That process, Vaccarello says, has always entailed keeping up with a “chaotic” pace and problem-solving in real time. “In the live space, you are living in that moment, and you have to have thought through all the things that could or would happen,” she says. “The way I look at it is: Figure out how to fix the issue and then we will worry about how it happened and how we fix it moving forward later. But in the moment, it’s going to be OK.”
She remembers the time the power went out in the middle of Jennifer Lopez’s 2019 Garden show (“That was a fun one, having to evacuate the building safely within 20 minutes”) and the night in 2004 that R. Kelly left in the middle of his double billing with Jay-Z. (Jay’s superstar artist friends at the show, like Mary J. Blige and Usher, stepped up onstage instead.) “It’s a moment, right?” Vaccarello says matter-of-factly. “And you have to pivot.” (“She’s unflappable,” Azoff says, “and in a crisis, you want someone unflappable there.”)
Vaccarello’s calm confidence, along with her on-the-ground knowledge of every element of her venues’ businesses, is at the core of what she calls one of the most important parts of her job: keeping close relationships with both artists and their teams. “Our entire ecosystem is based on relationships,” she says. “So it’s important to maintain [them] to make sure that we are part of the conversation every step of the way.”
Often, that has meant growing artists through MSGE’s portfolio of venues — as she did with comedy king Sebastian Maniscalco, who started at the Chicago Theater before advancing through New York’s Beacon Theater and Radio City to the Garden, where he set the record for most consecutive comedy shows at the arena (four) in 2019 and set it again in 2024 (five). “We’ve been with him since the beginning,” she says. “That trajectory and that relationship have mattered in his decision-making.”
Styles’ mega-residency is, Vaccarello says, a direct result of that relationships-first approach. Two years ago, following Styles’ 15 consecutive Love On Tour shows at the Garden in 2022 — which grossed $63.1 million, according to Billboard Boxscore — she started a conversation with the artist and his team (including his manager, Jeffrey Azoff, who praises Vaccarello’s ability to be “kind, cool and collected through it all”) about trying for 30, a number she says she knew would “instantaneously” sell out. “We love him, and we love that he feels this is his home,” Vaccarello says of Styles. “And I do think the model of fans going to the artist is going to stick around for a while.”
Together, Together expands the template set by one of the Garden’s best-known successes, one in which Vaccarello was closely involved: Billy Joel’s 10-year monthly residency, which ended in 2024 after grossing $266.7 million across 104 shows. During those years, “Jo really began to distinguish herself and evolve herself [professionally],” says Dennis Arfa, Joel’s longtime agent and chairman of the music division at Independent Artist Group. “Jo was a very innovative partner as far as the marketing, and she always represented a fairness between the venue and the artist. She threaded that needle extremely well.”
So well that, when Garden honcho James Dolan casually asked Arfa backstage one night who he thought should be named president, he recalls saying “Josephine” without hesitation. “I went through five presidents at Madison Square Garden,” Arfa says, “but the person who always seemed steady and consistent and had the correct vision was Josephine.”
At Sphere, which since its September 2023 opening has grossed $1.2 billion across 306 concerts, Vaccarello’s blend of data- and gut-based instincts have allowed her to easily direct both business and creative conversations. “We’re looking for artists who are coming to us with a vision and literally will explain what it is and what they want to put forth to the world and where they want to take their fans,” she says. She likens her relationship with Sphere acts to “basically a marriage: You’re looking at a year of we’re here working together … It’s a very different endeavor than typical touring.”
The Backstreet Boys’ Into the Millennium Sphere residency — the venue’s fourth-highest grossing run so far, with $156.4 million earned to date, which returns around the holidays and includes a New Year’s Eve show — was its most culturally pervasive since U2 inaugurated the venue in 2023. Celebrities flooded social media with videos of both the group’s choreography and futuristic visuals and selfies of themselves in the shows’ unofficial uniform of Y2K-all-white. “I knew it would have that pop culture effect,” says Vaccarello, whose own first arena show was New Kids on the Block at the Nassau Coliseum as a preteen. “I also knew that it was going to bring a lot more women to the venue. It was reliving nostalgia in a different way than the other bands who came before that.”
Next year, John Mayer will become the first artist to play Sphere as part of two different acts: first with Dead & Company, whose 48-show residency he largely produced creatively (and which grossed $198.9 million), and then in 2027 headlining under his own name with a three-pronged show including his solo music, a full band and the John Mayer Trio. He calls Vaccarello both the “matriarch” and “translator” of Sphere and describes how in the most to-the-point calls she can immediately set his mind at ease.
“She’s such a plain dealer and good communicator that I probably don’t even notice the back and forth she’s doing, representing both the sides of creative and of the Sphere,” Mayer tells Billboard . “I mean, she’s made it seem effortless.” On a recent call he had with his manager, Irving Azoff, and Vaccarello, “[In] all of three minutes, she kind of put everything in instant perspective and said, ‘Yeah, we could do that’ or ‘No, that’s tough to pull off.’ And it just felt like she was telling me the truth each time. It’s very hard to get that picture sometimes from people, and she gives an immediate lay of the land because she knows the lay of the land so well.”
That ability to channel both realism and ambition into results is also at the root of Vaccarello’s “unique bond,” as Azoff puts it, with Dolan. Arfa describes Vaccarello’s communication style as especially well-suited to working closely with MSGE’s executive chairman/CEO. “Part of her dealing with Jim is her ability to adapt and not be confrontational but be honest — give her opinion and let the cards fall where they may and work around that,” he says.
For her part, Vaccarello sees her relationship to Dolan in fairly clean-cut terms: “Jim is a visionary — and it’s my job to bring his vision to life,” she says. “He is also deeply committed to both the artist and guest experience and challenges us to think differently and innovate to make the experience in our venues unlike anywhere else.”
She acknowledges how much the arena world has evolved since she started out, a time when she remembers fans still camped out on the street for concert tickets. “We are seeing lots of artists coming up quicker, like Olivia Dean or Noah Kahan, who go to the arena or stadium level really quickly,” she says. Though the Garden is booked about a year-and-a-half out, she aims to leave some openings in the schedule to allow for risks that pay off — like when Punjabi star Diljit Dosanjh sold out two nights at the Garden in May, grossing $5.1 million.
She also notes how “the way venues and artists talk to fans has changed,” adding that “it’s critical that we’re reaching fans where they are, which means leaning into more nontraditional media and social,” as well as any way a show can become a more immersive, tailored experience (even if that simply means a specialty cocktail).
Comedy and podcasts have also “grown exponentially” as both arena and theater draws, Vaccarello says. Under her leadership, comedian residencies at the Beacon (including Jerry Seinfeld’s recurring one) have become a regular presence. It was a conversation she had with WME’s Mike Berkowitz that led to planning John Mulaney’s early-2027 nine-show run that will hit a series of iconic, increasingly larger venues in New York, including the Beacon, Radio City and the Garden.
“It sold out so quickly, we probably could have done multiple Gardens, but I think it’s more memorable this way, and it’s thanks to JoJo thinking of these type of things,” Berkowitz says. “She gets that comedy in a theater is an incredible experience” — though by the same token, he adds that Vaccarello is “very, very responsible for making arena comedy work for the artist and consumer.”
Mulaney’s shows are just one of the many things Vaccarello is excited to see on the immediate horizon at her venues. She’s thrilled that Radio City now has Sphere Immersive Sound installed — an innovation first deployed at the Beacon before the Las Vegas venue itself — which she says made this past year’s Les Misérables: The Arena Concert Spectacular (a semistaged production of her favorite musical) “feel like they were singing to you in your living room.” She describes how this year’s Christmas Spectacular will for the first time feature the Rockettes in a contemporary dance number, plus camera technology that will give audiences a closer-than-ever view of the troupe’s precision work. And on Jan. 2, 2027, Phish will play its landmark 100th show at the Garden, becoming the only act besides Joel to reach that milestone.
“Phish’s relationship with Madison Square Garden has become such an important part of our history, and JoJo has been a huge part of making that possible,” band frontman Trey Anastasio tells Billboard . “Whether it’s been helping us pull off some of the bigger ideas at the Garden or supporting what we’ve been able to create at Sphere, JoJo has always approached those ideas with enthusiasm and a real desire to figure out how to make them happen.”
It goes without saying that Vaccarello will be found at at least one of those shows, though not in some tony executive box. After perhaps grabbing her favorite arena snack — a maple-pepper bacon stick the Garden catering makes special for her — she’ll probably “scoot in” to her favorite place to watch a concert from: a little staircase house right near backstage. “I couldn’t tell you the last time I actually sat for a show,” she says with a smile. “That’s not who I am as a person.”
This story appears in the Nov. 7, 2026, issue of Billboard.