The chain of events that led to the rapper Macklemore’s ejection this week from a concert tour for the sin of proclaiming “Free Palestine” before a screaming football stadium in New Jersey unfolded in trite and predictable fashion. First, a real estate developer with fewer than 1,000 X followers and a surname pronounced like “whine” garnered 4.5 million views with a lengthy post recounting his experience purchasing $180 worth of Ed Sheeran tour merchandise only to be insulted with a “lecture on Middle East politics” from an apparent serial abuser of “tropes.” Then, an antisemitism nonprofit backed by billionaire casino heiress Miriam Adelson launched a petition urging friends of Israel to pressure Sheeran to renounce his opening act, and billionaire football/antisemitism mogul Bob Kraft joined forces with the billionaire owners of six other football teams from cities remaining on the schedule to order Sheeran to banish Macklemore from the tour. After a full week of tension-filled meetings and a 40-minute personal phone call with Kraft, Sheeran complied, cementing a familiar cycle.
But then something strange happened: A tidal wave of public backlash turned Macklemore into the undisputed victor of the PR skirmish. All four of Sheeran’s other opening acts quit the tour in solidarity. Celebrities from former star NFL quarterback Colin Kaepernick to beloved children’s YouTube personality Ms. Rachel to Broadway actress Allie Trimm chimed in to share stories of oligarch silencing. Ticket prices for the remaining dates of Sheeran’s tour on the resale market collapsed. And internet sleuths began picking apart the sordid personal history of Robert Kraft, who by the close of the news cycle had even pledged to donate $2 million to humanitarian relief in Palestine, issuing a statement saying: “I believe deeply that all lives are worth protecting.”
The day before Macklemore’s offending performance at MetLife Stadium, the concert promoter who had spearheaded the tour sent a beseeching letter to David Teslicko, the acting antitrust official ostensibly in charge of finalizing the consent decree the Justice Department will impose upon Live Nation as a condition of the Trump administration’s absurd, Ari Emanuel–inspired decision earlier this year to drop its comprehensive antitrust case against the concert monopoly.
“My name is Louis Messina, and I am founder of Messina Touring Group, [and] I write this letter because I am concerned the music industry is broken,” he wrote, humbly identifying himself as the concert promoter of such luminaries as Sheeran, Taylor Swift, and George Strait. “While I am of course worried about the survival of my own business, I am more worried about the entire music industry falling into the hands of one company. Most artists, agents, and managers are afraid of speaking out against Live Nation because they could lose everything if Live Nation turns against them. Live Nation already has turned against me. I have nothing to lose so I can tell it like it is. If Live Nation keeps its monopoly money, and if Live Nation prevents artists from using other promoters at their amphitheaters, it is not just going to result in fans paying more money. It will result in one company controlling the entire pipeline of talent.”
As Messina explained in the letter, 2025 was one of the worst summers he had known in 55 years in the concert business. At some point in the fall of 2024—emails unsealed in the case suggest the relationship began to break down about three weeks before the election—Live Nation had stopped returning his calls. This was a devastating blow, because the concert juggernaut owns or controls some 56 of the 88 outdoor amphitheaters that are the most sought-after venues for performing during the summer concert season; the next-biggest operator had just four. His longtime client, singer-songwriter Shawn Mendes, had just started a tour featuring a handful of Live Nation venues, so final negotiations had to literally be handled by Mendes’s talent agent. Another Messina act, The Lumineers, was then forced to defect to Live Nation just to have a shot at booking their favorite amphitheaters, and Mumford & Sons, a foe of concert corporatization that had been in talks to organize a bespoke tour with Messina, was forced to use Live Nation as well. Booking Sheeran’s tour was likely Messina’s least painful job of the year, thanks in part to the hundreds of millions of dollars in tickets, concessions, and parking fees he’d blanketed upon the 23 NFL stadiums that won coveted slots on Swift’s “Eras Tour” in 2023 and 2024.
The Eras Tour was also, of course, the likely genesis of Live Nation’s feud with Messina, having touched off the firestorm of populist rage that had inspired the Biden administration to fast-track an antitrust case against the music leviathan—a fury Messina cannily stoked by booking Zach Bryan’s Live Nation–free “All My Homies Hate Ticketmaster” tour a few months later. But Messina, who had founded his first concert promoter PACE Concerts (now part of Live Nation) back in 1975, and had made so much money over the years for Ticketmaster, and engendered so much loyalty among uniquely profitable performers like Swift and Sheeran, was shocked that the concert monopoly would go into all-out war with him, especially in the middle of an active comprehensive federal antitrust investigation with bipartisan support. “What I experienced in 2024 drove home how easy it is for Live Nation to destroy my business, like it has destroyed other promoters, and how something needs to change or Live Nation will always be able to hold the industry hostage,” he wrote.
It was during this hostage standoff that Messina signed Macklemore to perform ten dates of Sheeran’s “The Loop” tour. It was Sheeran’s request: The two had become famous around the same time in 2012, performed a sappy song together about the birth of Macklemore’s first child, and more recently the rapper had caused a minor earthquake in the area of the stadium when he opened a concert for Sheeran in his hometown of Seattle.
Macklemore was a man after Messina’s heart, a do-it-all artist who lucked into one grassroots hit album, winning Grammys and billions of Spotify plays. But the industry had no incentive to nurture a 30-year-old DIY guy whose breakout album featured a track shredding one of its towering moguls (and longtime Live Nation board member), so he had little to lose when Israel began dropping 2,000-pound bombs on Gaza. Most recently, he is best known for the infectious “Hind’s Hall,” a rapid but thorough summation of the first six months of mass murder and gaslighting in Gaza, made somehow more devastating by its delivery from such a generally accepted lightweight.
The song surged quickly to the top of mostly irrelevant charts like the iTunes Top 100 but disappeared just as rapidly. YouTube throttled the video with tight age restrictions. Spotify users accused the platform of suppressing the song, which was never added to Macklemore’s artist page and is still impossible to find if you don’t know its name. At last check, it had been streamed 39 million times; his hit “Can’t Hold Us,” by contrast, has more than 3.5 billion streams. Outside his hometown of Seattle, where he was invited to play two Palestine benefit concerts hosted in public parks, Macklemore would never get the chance to play “Hind’s Hall” live; a Las Vegas music festival that invited the rapper to perform during the summer dropped him at the last minute after Bill Maher devoted a segment of his show to savaging him. He spent much of the summer concert season in Europe, which may have been where he reunited with Sheeran.
Two weeks after the song’s release, the Biden administration filed the comprehensive antitrust complaint whose first sentence explained why it was so easy for the music industry to shut out a gadfly like Macklemore: “One monopolist serves as the gatekeeper for the delivery of nearly all live music in America today: Live Nation, including its wholly owned subsidiary Ticketmaster.” Live Nation subsidiaries or affiliated entities served as talent managers for hundreds of the most popular pop musicians, concert promoters for hundreds more, owner/operators of hundreds of the world’s top concert venues, and the ticket scalper of something like 80 percent of the event tickets sold in the United States. Ostensibly independent stadium management companies or talent management firms also comprised part of a “self-reinforcing” constellation of allied entities management called the Live Nation “flywheel.”
A critical node on that flywheel, the complaint explained, was a company called Oak View Group, co-owned by Irving Azoff, the legendary talent agent who as Ticketmaster CEO masterminded its merger with Live Nation, and Tim Leiweke, the co-founder and former longtime CEO of Live Nation’s biggest competitor AEG. OVG’s primary business is stadium management and concessions, but under its auspices Azoff and Leiweke colluded with Live Nation for years, the lawsuit alleges, to steer ticketing contracts to Ticketmaster. OVG worked with the private equity giant Silver Lake Partners to sabotage a fledgling ticketing firm in which Silver Lake Partners had invested, and with Dallas Cowboys owner Jerry Jones back in 2018 to rig the bidding process for a new UT Austin stadium. Azoff, Oak View, and Jones are also all partners of varying degrees with Miriam Adelson’s Sands casino empire, which was an early backer of Azoff and New York Knicks owner James Dolan’s Sphere project; Oak View is developing a $10 billion resort on a plot of land owned by the son of the Sands CEO, and two months ago Adelson, who has been working with Jones—along with Kraft one of the earliest investors in DraftKings—for years to lobby for legalized sports betting in Texas, hired the Dallas Cowboys owner’s Legends to oversee the development of a new arena for the Dallas Mavericks.
The Live Nation monopoly is actually just a piece of a larger public gathering spaces syndicate, which is why the state attorneys general involved in the antitrust case took the unprecedented measure of rejecting the Trump settlement and hiring their own trial attorney to press on with the antitrust trial last spring, which they ultimately won; now the judge must prescribe structural remedies with which he knows neither the company nor the DOJ will cooperate.
In any event, especially since the 2017 massacre at a Las Vegas music festival organized by Live Nation, all the interconnected actors comprising the public spaces monopoly have invested heavily in security and surveillance technology. Madison Square Garden uses facial recognition technology to boot random staffers of law firms that have sued Dolan, while Kraft’s antisemitism nonprofit the Blue Square Alliance Against Hate, which spent $62 million and collected $135 million in donations in 2024, keeps a “command center” based in Gillette Stadium that claims to monitor between 500 million and one billion social media posts a day with the help of a massive dashboard originally built for the Patriots coaching staff to analyze plays. When the head coach of the New York Jets showed up at work the morning after sporting a tiny Lebanese flag on his sleeve at a 2024 game in London, the director of security escorted him out of the building like a criminal. It’s easier to imagine Macklemore getting flagged by keffiyeh detection surveillance cameras than it is to understand how he wrestled his way on to the main stage, except for one thing: The million-dollar paycheck he negotiated with Messina suggests that even in his diminished, shadow-banned state, his name could be trusted to fill seats.
But when he screamed “Free Palestine” in the Jets’ home stadium, it was easy to see the old flywheel swing into action. Adelson’s Israeli-American Council referenced it right there in its Instagram post, urging its followers to sign the petition calling on Sheeran, Messina, et al. to eject Macklemore from his remaining tour dates, and then to “Contact Live Nation: Send your message directly to one of the world’s leading concert promoters and ticketing companies!”
Of course, Live Nation had virtually nothing to do with the Sheeran concert, something the IAC obviously knew, given that the group had accurately addressed its petition to Messina. (Live Nation directed an inquiry from the Prospect to Messina and refused to answer follow-up questions as to whether the company had approved the IAC’s request for fans to engage the company, been a party to the stadiums’ negotiations with Messina and Sheeran, blacklisted Macklemore from its own venues, or consulted Kraft’s Blue Square Alliance Against Hate in its own evaluations of artist speech.) The only material relevance Live Nation could claim in the dispute was that its subsidiary Ticketmaster had handled most of the ticketing, and would thus be the middleman on any refund requests. In a rational world, then, Live Nation would have had every motive to broker a peace, encourage cooler heads to prevail, and convince Kraft and his fellow billionaire stadium mafiosos to allow the show to go on as advertised.
But it is not a rational world, as the former San Francisco 49ers quarterback Colin Kaepernick, who was blacklisted from the league after organizing a contingent of players to kneel during the national anthem in silent protest of police brutality, observed in an interview this week: “The part that I hope people take away in this moment is what Robert Kraft and what they’re saying by denying Macklemore the opportunity to perform with Ed Sheeran is they are willing to collude. They are openly colluding,” he said, reminding listeners that the mere concept was dismissed as a “conspiracy theory” when he first filed a union grievance alleging that team owners had pledged not to sign him to so much as a practice squad.
Which is almost certainly why the IAC invoked Live Nation in their petition, though a spokeswoman declined to officially comment. None of the team owners had any desire to cancel a concert, shell out for millions of dollars in refund checks, lose out on millions more in concessions and parking fees, and engender the hated and resentment of their most loyal customers because Macklemore said “Free Palestine.” The only force that could have possibly motivated seven billionaires to issue an ultimatum that was practically guaranteed to explode in their faces regardless of the outcome was a threat on their own revenue the likes of which only Live Nation could make, the same threat the SeatGeek founder and the former Barclays Center CEO and Lou Messina had all vividly described to the federal judge in the antitrust case: the threat that Live Nation would simply stop taking their calls.
Whatever threats were issued, Messina, who is approaching 80 years old, could certainly see it all coming a mile away. He was at then-upstart AEG when his clients were the Dixie Chicks, one of whom expressed her own thoughts about George W. Bush after he invaded Iraq, and swiftly got blackballed by the entire industry. In a documentary about the backlash, Messina recalled radio stations not just refusing to play Dixie Chicks songs but refusing to air paid commercials for their concerts.
By the time October 7 came around 20 years later, the flywheel needed virtually nothing in the way of organic public sentiment to silence an entire generation of pop musicians. But that wasn’t going to last forever. Little by little, musicians cautiously stepped out, though far more hesitantly and in fewer numbers than their counterparts in the movie business, because actors can make a living doing podcasts, but most musicians make 90 percent of their income playing concerts, and the Live Nation flywheel can make that income stream evaporate overnight, especially in America. Even, theoretically, if your name is Ed Sheeran.
But what Sheeran somehow failed to grasp, perhaps as a result of having been raised by art-world parents whose clients included Prince Charles, and having had his success steered by Azoff protégé/Hollywood royalty Casey Wasserman and been paid to play at Kraft’s 2022 wedding to a woman 42 years his junior, was that at the end of the day, it’s the fans who fill the seats. And in 2026, even the average Ed Sheeran fan is astute enough to understand that, when a billionaire from the Epstein files tells you something is “hate speech,” that’s probably because it’s true.
