Trump’s Madison Square Garden Rally Was Bizarre—And Here’s a Portrait to Prove It

Staten Island artist Scott LoBaido, a longtime Trump supporter, revealed a New York–themed painting of the 45th president.

Artist Scott LoBaido speaks next to his portrait of former US president and Republican presidential candidate Donald Trump during a campaign rally at Madison Square Garden in New York on October 27, 2024. Photo: Angela Weiss / AFP.

Just days before Election Day on November 5, and the day after New York City set a record on Saturday with its early voting numbers, Republican presidential candidate Donald J. Trump returned to his hometown to follow through on a long-held dream: staging a rally at Madison Square Garden. A capacity crowd of 19,500 filled every seat on Sunday as an overflow crowd watched from outside. 

Much of the programming was familiar from other rallies and from the Republican National Convention: Hulk Hogan tearing off his shirt. Elon Musk predicting drastic budget cuts. Advisor Stephen Miller claiming that Trump would bravely say that “America is for Americans and Americans only.”

But a few things were new. This time, there was even fine art. A longtime Trump fan, Staten Island artist Scott LoBaido, took to the stage to unveil a red, white, and blue painting of the 45th president embracing the Empire State Building in the same unique manner he often hugs the American flag, whose stars and stripes ripple in the background. Limited edition prints of the image are also available on the artist’s website. (Comparisons to King Kong, one imagines, are incidental.) 

an artist unveils a portrait of a fireman against a red white and blue background

Artist Scott LoBaido unveils a portrait of firefighter Corey Comperatore, who was killed in an assassination attempt on former US president and Republican presidential candidate Donald Trump, ahead of his rally in Butler, Pennsylvania, on October 5, 2024. Photo: Jim Watson / AFP.

LoBaido also recently painted a tribute to fireman Corey Comperatore, who was killed in Butler, Pennsylvania on July 13, when Thomas Matthew Crooks made an attempt on Trump’s life. 

The same artist undertook a guerrilla art project this month, posting yellow and black signs with Trump’s distinctive profile on them around Staten Island, Bay Ridge, and other parts of the city, perhaps suggesting “Trump crossing” in anticipation of Sunday’s rally. Before it was revealed that he was the creator of the signs, LoBaido had posted a video on October 5 saying: “I don’t know who’s doing this but this is fucking genius. They’re all over the city. Now that is clever.”


A week later, the New York Post revealed that the artist himself had been photographed putting the signs in place. 

During Trump’s 2016 campaign, Staten Islander Sam Pirozzolo erected a 12-foot-high sign on his lawn in the form of a letter T—a LoBaido sculpture titled Freedom of Speech—which vandals set aflame. LoBaido replaced it with a 16-foot-high version.

On Sunday, Trump hit the stage two hours late, which has become routine during his recent appearances, and spoke for nearly 80 minutes as the crowd thinned out. 

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