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Republican presidential nominee Donald Trump on Sunday is set to use one of the biggest stages in the nation’s biggest city to take one of his final swings in the razor-tight 2024 race for the White House.

It’s a classic Trump move to throw a splashy campaign event at a venue that bills itself as “The World’s Most Famous Arena” – Madison Square Garden. Also in classic Trump fashion, it is a strategic decision that’s perplexing to seasoned political types who question why the former president would focus his limited time and resources as the clock ticks toward Election Day on Nov. 5 to travel to a seemingly safe Democratic state like New York.

Trump and his aides say there are good reasons to do this rally on the presidential campaign’s penultimate weekend. His command of the media and ability to attract eyeballs has always been pivotal to his success – and a hallmark of his fame starting out in New York in the 1980s. That’s an essential ingredient he’s looking to keep on capturing in his race against Kamala Harris, who brought new energy and her own wave of positive press since catapulting to the top of the Democratic ticket this summer upon President Joe Biden’s decision to only serve one term.

“It’s MSG, it’s Madison Square Garden,” Trump recently told FOX News Radio’s “The Brian Kilmeade Show,” adding: “That means a lot, those words, Madison Square Garden, right? Don’t you think so?”

Sunday’s rally comes after a steady stretch of events where Trump has taken back the spotlight, from working the fry cooker and handing out meals last Saturday at a McDonald’s in Pennsylvania to questioning Harris’ racial identity, spreading debunked claims about Haitian immigrants eating pets, making dire threats about the “enemy within” and talking about Arnold Palmer’s genitalia while visiting the dead golfing legend’s hometown about an hour outside Pittsburgh.

Those moves and many more may have helped to keep the polling in the presidential campaign neck-and-neck headed into the final stretch, even while frustrating some in the GOP by taking Trump away from his main talking points about the economy and immigration. Now the Republican candidate is heading for one of his few remaining campaign days far afield of the swing states, which has some political observers dumbfounded even as his team says it is a smart strategy to grab media attention that will be beamed nationwide.

“It makes no strategic sense,” said Trump biographer Tim O’Brien, who wrote ‘Trump Nation: The Art of Being the Donald.’ He added, “This is just King Kong climbing the Empire State Building again.”

A historic venue for a historic election

Madison Square Garden – there have been four arenas with the same name at three different Manhattan sites since 1879 – has long been a historic venue of choice for entertainers and politicians. Trump will join past presidents such as Franklin Delano Roosevelt, Dwight Eisenhower, John F. Kennedy and Richard Nixon in the Garden playlist.

The current MSG, which opened in 1968, has hosted events ranging from the 1971 “Fight of the Century” between Muhammad Ali and Joe Frazier to political conventions that nominated Jimmy Carter, Bill Clinton and George W. Bush en route to White House victories. It is the home of New York Knicks basketball and New York Rangers hockey.

The previous Garden also hosted an infamous event that Trump critics have emphasized in the run-up to Sunday. The German American Bund, a pro-Nazi group, held a rally at the Garden in 1939, two years before the U.S. entered World War II. That moment has come up in recent days after former Trump chief of staff John Kelly said in a New York Times interview that the former president said “more than once that, ‘You know, Hitler did some good things, too,’” accusations the former president immediately rejected.

Ahead of the Madison Square Garden rally, Trump insists he is making a serious bid for New York state, which with its 28 Electoral College votes makes it the fourth biggest prize of 2024 after California (54), Texas (40) and Florida (30).

Harris is staging big media events of her own, including Friday’s rally in Houston with cultural icons Beyoncé and Willie Nelson that Democrats hope can help propel their Senate candidate Collin Allred toward an upset of two-term Republican Sen. Ted Cruz. The Democratic presidential nominee also is planning an event on Tuesday at The Ellipse near the White House in Washington D.C. – site of the Trump rally that preceded the insurrection of January 6, 2021.

But Trump’s aides also acknowledge an upset in the Empire State is a long shot in the same way California is Harris country and Texas and Florida are in the GOP camp. They instead describe Sunday’s event as part of Trump’s ongoing effort to host media events that will draw national attention while making the way into the battleground states.

Trump has always sought creative ways to get attention, from his ride down an escalator in the lobby of his namesake Trump Tower before his presidential campaign announcement in 2015 to the photo op last Sunday at the McDonald’s. This cycle, he also has generated buzz with a triumphant return to the Pennsylvania site where he was shot in the ear two months earlier by an attempted assassin.

“It’s all about the media,” one aide said, and, in this case, “New York is the media capital of the world.”

Also, his aides said, Trump is a native New Yorker and has always wanted to be the main act at the Garden. He’s been a regular presence at the 19,500-seat arena over the years and said in a recent interview that he saw the Ali and Frazier fight there more than a half century ago, calling it “maybe the greatest event.”

Not that all of Trump’s memories are fond. In 2019, then-president Trump heard boos when he walked into the Garden for a UFC fight. Gwenda Blair, a longtime Trump biographer, noted the Garden is associated with rock stars, celebrities and fighters – playing into the larger-than-life image Trump cultivates.

“That imagery surrounds it – the whole kind of combination of rock star and heavy weight champion,” said Blair, author of ‘The Trumps: Three Generations That Built an Empire.’ She added: “Those things are so palpable in that, and so much referenced when you say Madison Square Garden. That’s going to be, in itself, a seeming crowning of him as the champ.”

A Republican nominee in New York, California

Trump allies reject the idea that there’s little or no strategic benefit to his New York rally.

In addition to attracting national media attention, they note it could help boost voter turnout for GOP U.S. House candidates. Trump will need congressional majorities to help him implement the second-term agenda he’s been promising on the campaign stump, and there are three House races in New York that are considered tossups, according to the nonpartisan handicapper The Cook Political Report, two with GOP incumbents and one with a Democrat.

The Republican presidential nominee also is holding a fundraiser around the New York event to collect much-needed campaign cash. Harris raised $222 million in September through her main campaign account, compared to Trump’s $63 million. Those figures don’t include other political committees that are raising large sums to support each candidate.

Former GOP House Speaker Newt Gingrich said Madison Square Garden will be “the high water mark” for Trump “because he really is a New Yorker, he’s really excited.”

“People keep saying: ‘Well, shouldn’t he be in Wisconsin? Shouldn’t he be… no. Every day he’s everywhere because television covers him,” Gingrich added. “He’s going to get enormous coverage at Madison Square Garden and he’s going to be happy and excited and the crowd is gonna be crazed.”

Trump held a rally earlier this month in Coachella in California, another blue state he has little chance of winning.

“This tactic of going into a noncompetitive media market or state in the final week of the election is not a typical strategy, but he’s not a typical candidate,” said Steve Caplan, who teaches political advertising and messaging at the University of Southern California and has worked for decades in Democratic politics doing media.

Caplan added that a rally at Madison Square Garden is “a great opportunity to get attention” but also could potentially turn off swing voters if it goes “off the rails.”

Harris’ campaign also has scheduled events outside the swing states. Her event in Texas on Friday with pop superstar Beyoncé highlighted the state’s restrictive abortion law as she makes abortion rights a centerpiece of her campaign. Trump staged a counter-programing event in Texas on the same day focused on immigration.

Rallying in New York and California in the final month of the election isn’t the only unorthodox part of Trump’s campaign strategy in the closing stretch. He also has dodged traditional events, like additional debates after going up against Harris in Philadelphia on Sept. 10, and mainstream media interviews that were likely to be more confrontational, most notably with the CBS program “60 Minutes.”

Trump has complained about his treatment from major television networks and threatened to revoke their broadcast licenses. He has devoted more time to conservative and alternative media outlets to try and fire up his base and reach casual voters.

While Trump has pushed himself into the spotlight more in recent weeks with provocative comments, Caplan said he wonders if that’s why the polls have tightened.

“It’s a good place for him in his mind, to be the center of attention in the closing two weeks, and he’s very good at that. But is it what’s affected the race specifically?” Caplan said, instead pointing to a change in the paid media strategy Trump’s campaign is deploying.

Trump’s campaign has pivoted to ads focused heavily on attacking transgender people and gender-affirming care. That may have helped drive up negative opinions of Harris after a stretch this summer where her approval rating shot up, Caplan said.

At the same time, the campaign is trying to drive voter turnout among Trump’s supporters, and the Madison Square Garden rally could help that.

“That is the game,” Caplan said “It’s about getting your voters mobilized and motivated.”

While New York may provide Trump with the biggest of the nation’s stages, it’s also another stop in the final push to the Nov. 5 finish line. The Republican, who hopes to join Grover Cleveland as only the second president to win non-consecutive terms in the White House, heads back to the swing states with rallies scheduled for Tuesday night in Allentown, Pennsylvania, and Wednesday night in Green Bay, Wisconsin.