He’s ‘Obsessed’: What Trump’s Madison Square Garden Rally Is All About

FOR THREE STRAIGHT PRESIDENTIAL CAMPAIGNS, Donald Trump mused about holding a rally at Madison Square Garden. Now it’s finally happening.

The ex-president’s campaign announced on Monday that he would appear at the world’s most famous arena on October 27, just nine days before voters head to the polls.

Despite Trump’s occasional boast, no one on his team actually believes that they have a chance at picking up New York’s twenty-eight Electoral College votes.

Instead, the event is a play for the candidate’s id.

Headlining Madison Square Garden represents the fulfillment of a longtime dream for an outer-borough kid who always has a New York state of mind, even after he technically became a Florida Man.

“I’m gonna fill the Garden,” Trump proudly boasted to a confidant who relayed the comment to The Bulwark on condition of anonymity.

Trump, the confidant said, “has just been obsessed with this for at least a year. This is his campaign. So it’s happening.”

It won’t come cheap. The campaign will probably shell out at least $1 million to rent Madison Square Garden, pay union labor to build the stage, and manage the event, a source familiar with the discussions said. The arena can hold nearly 20,000 people.

Trump has privately fumed in fundraisers about the cash gap between his campaign and Vice President Kamala Harris’s, as the New York Times reported this weekend. But his advisers say they have more than enough money to cover the hefty MSG expense and remain competitive in advertising through November 5. They say Trump plans a fundraiser around the rally, as he often does. They also justify the event as an effective way to attract broad attention because the national media is based in New York City and, as they see it, can never resist amplifying coverage in its backyard.

Trump’s rally in the Bronx in May attracted outsized attention. So too did his various appearances for his New York trial, where he would often go on days when his attendance was not required just to hold court with the press. They believe Madison Square Garden will guarantee more buzz and coverage.

“Madison Square Garden has already paid for itself,” crowed one Trump adviser.

Said a second adviser: “It’s great optics. Optics matter.”

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TRUMP WILL BE JOINING A LONG LINE of presidents over the last century who spoke at Madison Square Garden in the final days of their campaigns, including both Hoover and Roosevelt in 1932,1 Roosevelt again in 1936 and 1940, Truman in 1948, Eisenhower in 1956, Kennedy in 1960, and Johnson in 1964. (All these were at the old MSG, demolished in 1968.) Most of these speeches were forgettable—FDR’s in 1936 being the exception—but all these candidates hoped a good showing at the Garden would give their campaigns a final boost of enthusiasm.

For Trump, the MSG event is part of the bicoastal rally-and-spectacle phase of his campaign, one that has seen him travel to other blue states this month, including California (in the Coachella Valley on Saturday) and Colorado (in Aurora on Friday). Trump’s campaign is discussing a rally in New Jersey as well—potentially at the Prudential Center in Newark—which will test whether the national media’s appetite for events in their backyard extends across the Hudson River.

A source who has discussed the rallies with Trump said the events in these blue states could influence some congressional races in the hopes that Republicans keep control of the House, where they have a paper-thin majority of 220–212.

“The reason we have a majority in the House right now is because of California and New York,” the source said. “You pick up a seat here, you pick up a seat there, the NRCC does its job and all of a sudden you’re not impeached on your first day in office.”

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Trump’s campaign describes each of the events as unique messaging opportunities (California progressivism under Harris; the toll of migration in Colorado; crime and immigration in New York). But ultimately the rallies settle into a familiar script. Trump reads his teleprompter for about 45 minutes and ad-libs for an additional 45 minutes or so. His desultory stream-of-consciousness speeches, farragoes of lies, exaggerations, and misstatements, have increasingly drawn negative press coverage focused on his age and sanity. The Trump campaign dismisses the criticism as elite chatter that doesn’t matter to his voters.

Trump’s town hall Monday in Pennsylvania took a strange and newsworthy turn when two people passed out at separate times in the audience. That prompted Trump to cut the Q&A session short so he could play his favorite musical hits like a DJ.

What’s important to the Trump campaign is controlling the news cycle—which explains why he has held fifteen events in the first fourteen days of this month—and reaching the right voters. The candidate has had a ubiquitous presence on male-centric podcasts like Flagrant (last week) and Full Send (today), on the latter of which Trump announced he would be a guest on The Joe Rogan Experience, the most popular podcast on Spotify. Reuters reported Monday that Harris may also appear on Rogan’s show, which has not confirmed either candidate as a guest.

Trump also recently recorded an episode with Bussin’ with the Boys (dropping this week) and he plans an appearance on Six Feet Under, a podcast with former professional wrestling star the Undertaker.

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AFTER A PERIOD of largely avoiding the press, Harris has embraced nontraditional media by appearing last week on Alex Cooper’s Call Her Daddy and on Howard Stern’s show. But Harris also made time for more traditional shows, such as The View and 60 Minutes. She is also set to appear on Fox News, as well as CNN for a town hall that was scheduled in light of Trump declining to debate Harris on that network.

On Sunday, Harris called out Trump for not releasing his health records and skipping that second debate with her.

“Why does his staff want him to hide away?” Harris said to applause in Greenville, North Carolina. “Are they afraid that people will see that he is too weak and unstable to lead America? Is that what’s going on?”

That prompted a response from the Trump campaign’s rapid-response team on X, which called Harris’s remarks “highly cringe” and accused her of “projecting.” Privately, Trump aides believe that Harris has been suckered into a more conventional approach while the ex-president is reaching audiences and driving coverage in more novel ways.

“We’re going around you guys in the media,” said a third Trump adviser who spoke on condition of anonymity. “And MSG? It is what it is. Trump is going to sell out Madison Square Garden and he’s gonna let everyone know and that’s a win.”

But Trump is not actually selling out the arena; admission is free.

“Doesn’t matter,” the adviser said. “Who cares about that?”

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Maybe Harris, who has trolled Trump before by booking an arena he previously used, will be inspired to have an event in Madison Square Garden herself, following the example of FDR holding a rally there five days after Hoover did.