‘He’s obsessed’: Why Donald Trump is willing to pay a fortune to host a rally at MSG

Donald Trump is reportedly fixated on hosting a rally at New York City’s famous Madison Square Garden arena, despite most political experts believing the Empire State and even Trump’s hometown of New York City are squarely in the blue column for 2024.

“I’m gonna fill the Garden,” he reportedly boased in recent days to a confidant, who spoke anonymously to The Bulwark.

The Trump ally added that the Republican “has just been obsessed with this for at least a year. This is his campaign. So it’s happening.”

The Independent has contacted the Trump campaign for comment.

The campaign plans to host a rally at the Garden on October 27, less than two weeks before Election Day, even though Trump lost New York by more than 20 points in the previous two presidential elections, with the most recent polling showing he’s probably due for another thumping.

So why bother going big in a state that hasn’t gone Republican since Reagan? There are a few plausible reasons.

One could simply be for hometown pride.

Trump, despite changing his legal residency to Florida in 2020, was born in New York City, and still derives part of his political appeal from his (often exaggerated) career as a New York real estate developer.

Another might be a combination of that pride plus the former president’s fondness for doing things people say he can’t.

“We just rented Madison Square Garden,” Trump said with evident glee last week at a rally in Scranton, Pennsylvania. “We’re going to make a play for New York.”

 “When I told some people in Washington, ‘I’m going up to New York, we’re doing a campaign speech,’ they said, ‘What do you mean, New York? You can’t ever — nobody can win. Republicans can’t win,’” Trump added at a rally last month in Long Island, New York. “I said, ‘I can win New York, and we can win New York.’ We’re going to win.”

A triumphant MSG spectacle might also replace a different memory Trump has in the arena. During a 2019 appearance at an Ultimate Fighting Championship bout, the then-president was reportedly showered with boos and negative signs, and Trump is famous for holding onto past slights.

Appearing in a state can have other benefits beyond winning it, too.

Trump’s presence in New York could help out Republicans on down-ballot races, or call attention to signature issues, like the former president using a recent rally in sapphire-blue California to hit out at his Golden State rival on the campaign trail, Kamala Harris.

Finally, from the man whose campaign brought you the $399 gold ‘Never Surrender’ high-top sneakers and a $100,000 bejeweled “victory” watch, the New York rally may just be a way to raise some sorely needed campaign cash, what with the Harris campaign cruising to more than $1bn in fundraising faster than any other in U.S. history.

The Trump campaign is selling an “Ultra MAGA Experience” for visitors to the rally that costs nearly $1m, though it has provided virtually no details on what the experience entails.

Whatever it means to go Ultra MAGA, the campaign is surely hoping to pack the arena for Trump’s big statement, despite efforts from online pranksters to reserve tickets then be no-shows.