The rally, held little more than a week before the election, offers Trump an iconic backdrop to argue that crime and inflation have ravaged a great city he once called home. Located at the doorstep of the national media in New York, it also promises him outsize attention in a saturated news environment.

The affair, estimated to cost his campaign more than $1 million, is just his latest detour outside of the battleground states as Vice President Kamala Harris competes for media coverage. There could be a more indulgent reason behind Trump’s choice of venue, however.

From his youth, Trump, a reality TV star-turned-politician, has watched the world’s greatest musicians and athletes perform at Madison Square Garden. Now, he will get his own chance to stand in the spotlight.

“He loves the crowd, he loves the rallies, he loves being on TV,” said Republican strategist Alex Conant, who spent his early childhood in New York City.

“I think to understand Trump, you have to understand that, at heart, he’s an entertainer, and Madison Square Garden is the ultimate destination for any entertainer,” Conant added.

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The Trump campaign is hoping to generate a similar buzz as that seen at his nominating convention in Milwaukee, with UFC CEO Dana White and singer Lee Greenwood reprising their roles as special guests.

Conservative celebrities like Tucker Carlson and X CEO Elon Musk will also appear onstage, according to a lineup released on Friday night.

Trump had been teasing an event at the arena since last year as he makes a long-shot play for New York. Last week, he visited a barbershop in the Bronx and twice before held rallies in the state.

But his decision to hold the Madison Square Garden rally now, in the closing days of the race, is decidedly sentimental.

In 2015, Trump launched his political career by riding down a golden escalator at Trump Tower in Manhattan. Nine years later, he will wind down his final run for president at Manhattan’s most storied arena.

“It’s just going to be a very exciting culmination of his years of effort, going back even before his famous” escalator ride, Rep. Elise Stefanik (R-NY), a New York lawmaker and chairwoman of the House Republican Conference, said of Trump’s Madison Square Garden rally. “Just the years he spent building up New York, literally helping build the skyline.”

Trump, 78, made his name as a playboy billionaire who developed some of Manhattan’s most iconic buildings. But his career in New York has come with as much controversy as success.

The district attorney in Manhattan successfully overcame Trump’s refusal to release his tax returns as president, raising the issue all the way to the Supreme Court.

Since then, Manhattan courts have found Trump liable for sexual abuse and, separately, manipulating his net worth. In May, a jury found him guilty of falsifying business records, with a sentencing to be handed down after the election.

Trump left New York in 2019 to take up residency in Florida, claiming he had been treated “very badly” by the city’s Democratic leaders. Yet his repeated visits evince an attachment to the state that will outlive his political career.

His allies, alleging the prosecutions are political, have framed Trump’s return as an act of defiance.

“New York is as close to home as it gets for the president. It’s where he grew up. It’s where his roots are,” said Lee Zeldin, an ex-New York congressman who nearly defeated Gov. Kathy Hochul in the 2022 governor’s race.

“They have been trying to take him down, imprison him, bankrupt him, kick him out of the state and office, and President Trump just keeps fighting,” he added.

Democrats have ascribed a sinister quality to Trump’s latest New York visit. Former Secretary of State Hillary Clinton, Trump’s 2016 rival, accused him of “reenacting” a Nazi rally held at Madison Square Garden in 1939.

In an effort to mock Trump, other critics encouraged their followers to buy tickets to the event so they can leave those seats empty. Trump is notoriously sensitive about his crowd sizes.

There is a certain practicality to Trump’s presence in the state. If he wins the presidency on Nov. 5, he will need a Republican-led Congress to enact his agenda, and the majority-deciding seats could run through New York.

Trump may lose the state, as he did by 23 points in 2020, but his footprint there could drive turnout in New York’s five competitive House races.

“There’s no greater coattails in politics in America than President Trump’s,” Stefanik said in an interview. She is one of four House GOP leaders, including Speaker Mike Johnson (R-LA), who will join Trump on Sunday.

Trump, for his part, has openly mused whether his foray into noncompetitive states is “foolish.” In addition to New York, he has hosted rallies in blue strongholds such as California and New Jersey.

But Trump could have a more aspirational goal in mind, one that eluded him in both of his prior races: winning the popular vote.

Democrats have won seven out of the last eight presidential elections when considering the raw vote count nationally, but Trump is virtually tied with Harris in the final national polls of the race.

In 2020, Trump was 8 points behind President Joe Biden at this point in the race, according to the RealClearPolitics polling average. He was 5 points behind Clinton at this point in 2016.

Harris has attempted to reclaim the momentum she held against Trump soon after she took over the Democratic ticket in August.

She made her own detour to right-leaning Texas on Friday in a bid to highlight the state’s restrictive abortion laws. Next week, she will deliver a “closing argument” in Washington, D.C., at the Ellipse, the site of Trump’s rally on Jan. 6.