On Sunday, Republican presidential candidate Donald Trump is scheduled to hold a significant campaign rally in one of the most iconic venues in the United States, Madison Square Garden, as he makes a last effort in the closely contested 2024 presidential race.

It’s a typical Trump move to host a flashy campaign event at a location known as “The World’s Most Famous Arena.” However, this choice raises eyebrows among seasoned political analysts who wonder why the former president is investing his time and resources in a Democratic stronghold like New York so close to the November 5 Election Day.

Trump and his team argue that there are solid reasons for choosing to rally in New York during the final weekend of the campaign. His media presence and knack for grabbing attention have always played a crucial role in his political journey, especially since he began his career in New York in the 1980s. Capturing media interest is vital as he competes against Democratic candidate Kamala Harris, who brings fresh energy and has garnered positive coverage since taking the lead on the Democratic ticket after President Joe Biden’s decision to not seek re-election.

“It’s MSG, it’s Madison Square Garden,” Trump said on FOX News Radio’s “The Brian Kilmeade Show.” He emphasized the significance of the venue, stating, “Those words, Madison Square Garden, mean a lot, right?”

The rally comes after a series of events where Trump has actively sought the spotlight, which included surprising interactions such as frying burgers and serving food at a McDonald’s in Pennsylvania, to making controversial remarks about Kamala Harris’ racial background, and discussing various topics, including his views on Arnold Palmer’s legacy in golf.

These actions have kept the race close in the polls, despite some GOP members being frustrated by Trump’s departure from key issues like the economy and immigration. Now, heading to New York for one of the last campaign events away from crucial swing states has left many political watchers puzzled, yet Trump’s team believes this approach will capture widespread media coverage.

“It makes no strategic sense,” commented Trump biographer Tim O’Brien, author of ‘Trump Nation: The Art of Being the Donald,’ remarking, “This is just like King Kong scaling the Empire State Building again.”

A Historic Setting for a Significant Election

Madison Square Garden, which has had four iterations since 1879, is a historic venue popular among both entertainers and politicians. Trump’s appearance will add him to the list of past presidents who have addressed audiences at this venue, including Franklin Delano Roosevelt, Dwight Eisenhower, John F. Kennedy, and Richard Nixon.

The current MSG, opened in 1968, has hosted notable events ranging from the legendary 1971 boxing match between Muhammad Ali and Joe Frazier to political conventions nominating Jimmy Carter, Bill Clinton, and George W. Bush for their respective presidencies. It is also the home of the New York Knicks basketball team and the New York Rangers hockey team.

Past controversies surrounding the old garden may resurface as Trump prepares for his rally. In 1939, a pro-Nazi group held a large rally at the venue, which critics of Trump have cited, especially following remarks made by former Trump chief of staff John Kelly about Trump allegedly making favorable comments about Hitler—a claim that Trump has denied.

As he looks ahead to the rally at Madison Square Garden, Trump plans to make a serious attempt to engage voters in New York, which is significant with its 28 Electoral College votes, making it the fourth-largest prize of the upcoming election after California, Texas, and Florida.

Meanwhile, Harris is conducting her own significant events, including a rally in Houston with celebrities like Beyoncé and Willie Nelson to support Democratic candidate Collin Allred in his challenge against two-term Republican Senator Ted Cruz. She also has an event planned at The Ellipse near the White House next Tuesday, a location linked to Trump’s earlier rally before the events of January 6, 2021.

However, Trump’s team acknowledges that winning New York is a challenging prospect, similar to how California is firmly in Harris’s camp while Texas and Florida lean Republican. They present Sunday’s gathering as part of Trump’s ongoing strategy to organize high-profile media events.

Trump is taking steps to draw national interest as he moves into crucial battleground states.

Throughout his career, Trump has always found innovative methods to capture attention, from his famous escalator descent at Trump Tower before announcing his presidential run in 2015 to his recent photo opportunity at McDonald’s. This election cycle, he also sparked interest with a notable return to Pennsylvania, where an assassination attempt occurred just two months prior.

“It’s all about the media,” commented one aide, emphasizing that “New York is the media capital of the world.”

Moreover, Trump’s aides mention that he is a New Yorker at heart and has long desired to headline events at Madison Square Garden. He has frequently attended events at the 19,500-seat venue and shared in a recent interview that he witnessed the legendary Ali-Frazier fight there over fifty years ago, describing it as “perhaps the greatest event.”

Not all of Trump’s experiences have been positive, however. In 2019, as president, he faced boos when he entered the Garden for a UFC fight. Gwenda Blair, a biographer of Trump, pointed out that the Garden is a place connected with rock stars, celebrities, and athletes – all elements that contribute to the larger-than-life persona Trump has nurtured.

“That imagery is so prevalent there – a blend of rock star and heavyweight champion,” said Blair, author of ‘The Trumps: Three Generations That Built an Empire.’ She added: “Those associations are strong, and they come to mind when discussing Madison Square Garden. This event could symbolize his crowning as a champion.”

A Republican Nominee in New York and California

Trump’s supporters dismiss the notion that his New York rally lacks strategic value.

They believe that in addition to generating nationwide media coverage, it could enhance voter turnout for Republican candidates in U.S. House races. Trump will need congressional support to fulfill the agenda he has been pledging on the campaign trail, and in New York, there are three House races considered uncertain, according to The Cook Political Report, which is nonpartisan—two involving Republican incumbents and one with a Democrat.

The Republican presidential candidate is also organizing a fundraiser around the New York event to raise essential campaign funds. Harris brought in $222 million in September through her primary campaign accounts, whereas Trump collected $63 million. These figures exclude other political committees that are amassing significant funds to support each candidate.

Former House Speaker Newt Gingrich remarked that the event at Madison Square Garden will be “the high point” for Trump, noting, “He is genuinely a New Yorker and is truly excited about it.”

“People keep asking if he should be in Wisconsin or another state, but no. He’s everywhere every day because he knows the media will cover him,” Gingrich added. “The coverage he will receive at Madison Square Garden will be immense, and he will feel happy and energized by the enthusiastic crowd.”

Earlier this month, Trump held a rally in Coachella, California—another blue state where his chances of winning are slim.

“His approach of visiting non-competitive states or media markets right before the election isn’t common, but then again, he’s not a typical candidate,” said Steve Caplan, a political advertising and messaging professor at the University of Southern California, who has been involved in Democratic politics for many years.

Caplan mentioned that hosting a rally at Madison Square Garden is “a fantastic opportunity for media attention,” but cautioned that it could alienate swing voters if things go awry.

Meanwhile, Harris’ campaign has planned events outside of swing states. Her upcoming Texas event with pop music icon Beyoncé highlights the state’s restrictive abortion law, cementing abortion rights as a crucial aspect of her campaign. On the same day, Trump is conducting a counterprogramming event in Texas that centers on immigration.

Trump’s rallies in New York and California during the final month of the election are not the only unconventional parts of his campaign strategy. He has also steered clear of traditional events such as further debates after his face-off with Harris on September 10 and has avoided interviews with mainstream media outlets that are likely to be tougher, particularly with programs like CBS’s “60 Minutes.”

Trump has expressed frustration over how major television networks treat him and has threatened to revoke their broadcast licenses. Instead, he has focused more on engaging with conservative and alternative media to invigorate his base and connect with more casual voters.

While Trump has placed himself in the spotlight recently with bold statements, Caplan is curious if that shift is why the poll numbers have tightened.

“In his mind, being the focal point during these final weeks is advantageous, and he excels at it. But I wonder if this has specifically influenced the race,” Caplan suggested, pointing to a change in Trump’s campaign’s paid media approach.

Trump’s campaign has shifted focus to advertisements that primarily target attacking his opponents.

Concerns regarding transgender individuals and the provision of gender-affirming care may have contributed to Harris’s declining approval ratings following a period of increase this summer, according to Caplan.

Simultaneously, the campaign aims to rally support among Trump’s base, and the rally at Madison Square Garden could be a strategic move toward that goal.

Caplan stated, “That’s the strategy. It’s all about energizing and mobilizing your voters.”

While New York offers Trump one of the largest platforms in the country, it also serves as a key stop as he intensifies his campaign efforts leading to the November 5 election. The Republican candidate aspires to be only the second president after Grover Cleveland to achieve non-consecutive terms in office. He will be visiting swing states again, with events planned for Tuesday evening in Allentown, Pennsylvania, and Wednesday evening in Green Bay, Wisconsin.