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Is James Dolan a Republican? Trump’s MSG rally suggests as much.
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Is James Dolan a Republican? Trump’s MSG rally suggests as much.

Always a front row seat.
Photo: Garrett Ellwood/NBAE/Getty Images

Until this weekend, Donald Trump he spent most of his time at Madison Square Garden as a member of the public watching the Knicks or Rangers with his children, his wifeand other celebrities such as 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 as one of the final stops on his third presidential campaign. Trump’s allies says he’s been “obsessed” with the idea for months, while a counselor said The Wall Street Journal that the rally will be a “pretty hot ticket” and that it will be “the biggest Trump rally I’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 Nazi rally at Madison Square Garden on February 20, 1939.” he posted on Twitter Brad Hoylman-Sigal, the state senator who represents the Garden 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 documents must have crossed the desk of its director and owner, James Dolan. For years, it’s been difficult to pin down the politics of Dolan, the billionaire son of the guy who co-founded HBO and who has donated to both Democrats and Republicans, switching parties seemingly at his convenience. (Dolan, notoriously infrequent with her press appearances, did not respond to requests for comment.) Ahead of Trump’s rally in Dolan’s garden, we gathered evidence of her political life to see what it looks like when it’s all in one place .

Like many billionaires, Dolan has donated a lot of money to Trump over the years. In 2016, he wrote a check for $300,000 to a Trump-supporting PAC. The following year, he returned with $125,000 donation at a Trump fundraiser the same week the president told the Golden State Warriors they couldn’t come to the White House to celebrate their NBA championship.

When ask of the donation at the time, a Knicks spokesman said Dolan was “a longtime friend and supporter of President Trump.”

In 2002, Dolan and about 400 guests traveled to Donald Trump’s resort in South Florida for his second wedding, which Trump and several people attended. other media executives. In 2018, Dolan cited his wedding at Mar-a-Lago as one of the reasons he is close to Trump in a rare interview with ESPN:

“I’ve known him for a long time. I got married at Mar-a-Lago. I am a member of Mar-a-Lago and support him as a friend. And you don’t have to agree with everything he does to support him. And he is, by the way, our president, and I don’t understand people who want our president to do harm. Why would you want your president to do harm? It’s like wishing your milkman would bring you sour milk.”

In 2022, Dolan, not one for dissent, found himself in trouble after barring members of the law firms that sued him — using facial recognition technology to prevent those lawyers from stalking his beloved Knicks and Rangers. By January 2023, Dolan had begun to lose the narrative of his lawyer’s dystopian repression, bringing props in TV interviews and claiming that facial recognition technology has been used since the earliest days of humanity. (He meant “eyes”)

In response to the PR crisis, Dolan hired Hope Hicks, Trump’s former adviser maybe or not they gave the former president COVID in the final days of the 2020 election. Hicks was according to reports a consultant, so it’s not clear what he actually did other than collect a significant fee. But lawsuits over the facial recognition mess have been thrown out of court.

In one of the most telling examples of Dolan’s relationship with money and politics, he donated to a Republican House candidate in New York after Democrats in the race mocked him. In 2020, then-Rep. Max Rose said that Dolan has to sell the Knicks because his constant torment with the formation he had destroyed the team. “Nothing is happening. Every year they don’t make the playoffs, New York City loses,” he told TMZ. “We are losing a piece of our soul. Sell ​​tomorrow. Sell ​​today. Do it for the good of us all, brother!”

In response, Dolan donated $50,000 to Republican candidate Nicole Malliotakis, who went on to beat Rose for her seat representing Staten Island and parts of southern Brooklyn. In the 2022 rematch, Dolan again donated to Malliotakis to make sure there was one less politician in New York he didn’t like.

In 2021, Dolan seemed to have a change of heart, at least locally. In New York’s first open primary, the billionaire entered the Democratic mayoral race to replace Bill de Blasio. Dolan donated $5,000 to former Citigroup executive Ray McGuire as well as $2,000 to former Republican Eric Adams. Most likely, Dolan saw an opportunity to influence the only mayor who mattered that year in the heavily Democratic city; also, $7,000 doesn’t mean that much to him. (Dolan also donated 5 million dollars to a group that educated voters about conservative 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 who might be interested in destroying the tax subsidy that allowed him to operate the garden above Penn Station without paying property taxes — a gift from Gov. state that saved him hundreds of millions over the years. Throughout Eric Adams’ many controversies, Dolan also remained loyal to the mayor, donating $5,000 to his legal defense fund after the feds seized his phones last November.

Political rallies at Madison Square Garden are surpassed only by 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 McGovernand 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 unprecedented and unprecedented in presidential history to court far-right white nationalists,” he said. “That’s the distinction we were highlighting.”

“I don’t know why we would hold James Dolan to any standard other than having the most notable sports arena and team,” he added. “But if we criticize him, we should criticize a number of Fortune 500 CEOs who are all for Trump and are New Yorkers.”