Until this weekend, Donald Trump has spent most of his time at Madison Square Garden as an audience member, watching the Knicks or the Rangers with his kids, his wives, and fellow celebrities like Howard Stern and —this will excite some conspiracists — John F. Kennedy Jr. But on Sunday, Trump will finally headline the world’s most famous arena himself as one of the final stops in his third presidential campaign. Trump allies say he’s been “obsessed” with this idea for months, while one adviser told The Wall Street Journal that the rally will be a “pretty hot ticket” and that it will be “the biggest Trump rally we’ve ever seen.”
Not everyone in the liberal bastion of New York City is as happy as the Trump campaign. “Allowing Trump to hold an event at MSG is equivalent to the infamous Nazis rally at Madison Square Garden on February 20, 1939,” tweeted Brad Hoylman-Sigal, the state senator who represents the garden’s district. “This is a disastrous decision by Madison Square Garden.”
Who exactly made the decision to book Trump is an open question, but at some point the paperwork must have crossed the desk of its hands-on CEO and owner, James Dolan. For years, it has been difficult to pin down Dolan’s politics, the billionaire son of the guy who co-founded HBO and who has donated to both Democrats and Republicans, swapping parties seemingly when it’s been convenient for him. (Dolan, notoriously sparse with his media appearances, did not respond to requests for comment.) Ahead of the Trump rally in Dolan’s garden, we’ve compiled the evidence of his political life to see how it looks when it’s all in one place.
Dolan has donated a lot of money to Donald Trump
Like many billionaires, Dolan has donated a bunch of money to Trump over the years. In 2016, he wrote a check for $300,000 to a Trump-supporting PAC. The next year, he re-upped with a $125,000 donation to a Trump fundraising committee the same week that the president told the Golden State Warriors they could not come to the White House to celebrate their NBA championship.
When asked about the donation at the time, a Knicks spokesperson said that Dolan is “a longtime friend and supporter of President Trump.”
He got married at Mar-a-Lago
In 2002, Dolan and some 400 guests traveled to Donald Trump’s resort in south Florida for his second wedding, which was attended by Trump and a smattering of other media executives. In 2018, Dolan cited his wedding at Mar-a-Lago as one of the reasons he is close with Trump in a rare interview with ESPN:
“I’ve known him for a long time. I got married at Mar-a-Lago. I’m a member of Mar-a-Lago, and I support him as a friend. And you don’t have to agree with everything that he’s doing in order to support him. And he’s, by the way, our president, and I don’t understand people who wish our president to do badly. Why would you wish your president to do badly? It’s like wishing that your milkman will bring you sour milk.”
He’s hired a former Trump staffer
In 2022, Dolan, not one for dissent, found himself in trouble after banning members of law firms who have sued him — using facial-recognition technology to bar these attorneys from watching their beloved Knicks and Rangers. By January 2023, Dolan began to lose the narrative on his dystopian lawyer crackdown, bringing props to TV interviews and claiming that facial-recognition technology has been in use since the first days of humanity. (He meant “eyes.”)
In response to the PR crisis, Dolan hired Hope Hicks, the former Trump aide who may or may not have given the former president COVID in the last days of the 2020 election. Hicks was reportedly a consultant, so it’s unclear what she actually did other than collect a significant fee. But the lawsuits related to the facial-recognition mess have been thrown out of court.
Dolan has donated to local Republicans out of spite
In one of the most telling examples of Dolan’s relationship to money and politics, he donated to a Republican House candidate in New York after the Democrat in the race made fun of him. In 2020, then-Representative Max Rose said that Dolan has to sell the Knicks because his constant tinkering with the lineup had destroyed the team. “Nothing’s happening. Every year that they don’t make the playoffs, New York City loses out,” he told TMZ. “We lose a piece of our soul. Sell tomorrow. Sell today. Do it for the good of all of us, brother!”
In response, Dolan donated $50,000 to Republican candidate Nicole Malliotakis, who ended up beating Rose for his seat representing Staten Island and parts of southern Brooklyn. In the re-match in 2022, Dolan again donated to Malliotakis to ensure there was one less politician in office in New York City who did not like him.
But he has also donated to Eric Adams and other New York Democrats
In 2021, Dolan appeared to have a change of heart, at least locally. In the first-ever open primary in New York City, the billionaire got into the Democratic race for mayor to replace Bill de Blasio. Dolan donated $5,000 to former Citigroup executive Ray McGuire as well as $2,000 to fellow former Republican Eric Adams. Most likely, Dolan saw an opportunity to influence the only primary that mattered that year in the extremely Democratic city; also, $7,000 does not mean that much to him. (Dolan also donated over $5 million to a group that educated voters about conservative-leaning platforms such as crime and how to stop the “exodus” from the city due to quality-of-life issues.)
But since then, he has donated hundreds of thousands to Democratic state assembly candidates to protect them from progressive upstarts that may be interested in killing the tax subsidy that has allowed him to operate the garden on top of Penn Station without paying property taxes — a gift from the state government that has saved him hundreds of millions over the years. Throughout Eric Adams’s many controversies, Dolan has also remained loyal to the mayor, donating $5,000 to his legal-defense fund after the Feds seized his phones last November.
Is an MSG Trump rally really that bad?
Political rallies at Madison Square Garden go beyond just Donald Trump and German American Nazis, with campaign events held there by politicians including Dewey Warren, Dwight Eisenhower, Lyndon Johnson, George Wallace, Richard Nixon, George McGovern, and Ralph Nader.
I presented this history to Brad Hoylman-Sigal, the senator who was criticized for comparing the Trump event to a Nazi rally. “I think Trump is unparalleled and unprecedented in presidential history for courting far-right white nationalists,” he said. “That is the distinction that I was spotlighting.”
“I don’t know why we would hold James Dolan to any standard other than that he has the most notable arena and sports team,” he added. “But if we’re critiquing him, we should be critiquing a number of Fortune 500 CEOs who are all in for Trump and are New Yorkers.”
