As Donald Trump prepares to attend Game 3 of the NBA Finals at Madison Square Garden on June 8, the spotlight is also on Knicks owner James Dolan’s longstanding political connection to Trump—including major campaign donations and social controversies—raising e
When Donald Trump steps into Madison Square Garden for Game 3 of the NBA Finals on Monday, June 8, it won’t just be a marquee sports moment—it will bring a level of security that some fans fear will change the experience of the trip itself.
Trump isn’t expected to arrive uninvited. He will be inside the arena as the guest of Knicks owner James Dolan. and Trump has said the two “go way back.” After the Knicks host their first NBA Finals game since 1999. Trump is expected to become the first sitting U.S. president to attend an NBA Finals game, with extra security precautions affecting some fans.
Trump’s longtime admiration for Dolan—and his public warmth toward him—has been part of the lead-up. Asked last week about whether he would attend when the Knicks play their first Finals home game since 1999. Trump told reporters. “Well. I’ve been a Knick fan for a long time. and I’m also a Jim Dolan fan.” Trump added that Dolan “is a nice guy. ” and described him as “a competitive guy” who “spent a long time wanting to win. and… he’s got a team that’s amazing.”.
Trump also praised the franchise direction Dolan helped shape: “He’s really great, a great team. I’m happy for Jim (Dolan) because Jim has really been fighting hard to produce such a team.”
That relationship matters not just because of who will be in the building. but because Dolan helped turn the Knicks into the kind of team that can carry a presidential visit. Dolan took over day-to-day operations of the Knicks in 1999. two years after his father. former Cablevision founder Charles Dolan. bought the team.
The money trail has been clear for years. Dolan is described as a major donor to Trump’s political operation. with Dolan giving $125. 000 to Trump’s re-election campaign efforts five days after Trump’s public spat with the then-NBA champion Golden State Warriors over a dispute about whether Stephen Curry had declined an invite to the White House or Trump rescinded the invitation. Dolan also previously donated $300,000 to Trump’s 2016 election campaign, according to Federal Election Commission filings.
A Knicks spokesperson said at the time, “Mr. Dolan is a long-time friend and supporter of President Trump,” adding that the contribution is “a matter of public record, and was made by Mr. Dolan as a private citizen.”
Even with that support, the political alignment hasn’t insulated Dolan from blowback. In October 2024. Trump held a rally at Madison Square Garden that was followed by controversy tied to comedian Tony Hinchcliffe’s remarks ahead of Trump. Hinchcliffe said Puerto Rico was a “floating island of garbage” before the rally.
Arena representatives pointed to venue history to respond to the criticism. They noted that former President Joe Biden had previously held an event at Radio City Music Hall, another property owned by Dolan.
“As a business we are neutral in political matters,” a Madison Square Garden official said in a statement. “We rent to either side. We don’t censor artists, performers or speakers.”
That “support as a friend” framing echoes Dolan’s own statements about Trump. Dolan has said he is a member of Trump’s Mar-A-Lago club. He also said he has supported Trump as a friend without endorsing every decision.
“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,” Dolan told ESPN in 2018. He added, “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.”.
Trump’s connection to the Knicks also holds a credential beyond fandom. NBA commissioner Adam Silver confirmed Trump’s status as a longtime Knicks fan last week when asked about the President’s potential attendance at Madison Square Garden.
“Donald Trump, before he ever ran for office, he was a big Knicks fan,” Silver said. Silver described how he saw Trump at games and drafts at Madison Square Garden during earlier years. saying Trump “attended many of our drafts when they used to take place at Madison Square Garden.” Silver said he hopes the appearance will “emphasize what we have in common. not what pulls us apart. ” and argued. “We’re seeing that in New York and I think President Trump is very much a New Yorker. and I’m thrilled that yet another New Yorker wants to participate in the enthusiasm and the joy around this Knick team.”.
But the Dolan-Trump relationship has also threaded into business and venue decisions—areas where politics and dealmaking can collide. The Trump administration has reportedly been involved in plans that. if approved. would lead to a massive renovation of Penn Station and moving Madison Square Garden from its current spot on top of the midtown Manhattan train station. The plan needs Dolan’s approval, and he initially declined interest in moving the arena.
The New York Post reported that Dolan and Trump met in April to discuss the Penn Station plans and the prospect of renaming Penn Station after Trump.
Dolan’s role as a communications and entertainment gatekeeper has also brought controversy, including at political ceremonies. As Madison Square Garden executive chairman. Dolan also runs the Rockettes Christmas show out of Radio City Music Hall in New York. For Trump’s first inauguration, Dolan agreed to have the Rockettes perform. The dancers faced social media backlash after the announcement. They were ultimately not forced to perform.
“This is a great national event,” Dolan told the dancers, according to a recording leaked to Marie Claire magazine. “Every four years we put in a new president. It’s a huge moment in the country’s history. It usually signifies a whole change in how the government is going to run. The fact that we get to participate in it … we are an American brand. and I think it’s very appropriate that the Rockettes dance in the inaugural and 4th of July and our country’s great historical moments.”.
Dolan added in the same recording, “A good portion of people voted for this person.” He added, “Hopefully they will like our brand. If 1% of 1% of them come to our show, we’re going to do great.”
Taken together. the facts point to a familiar pattern around elite New York institutions: Dolan’s proximity to Trump spans campaign finance. venue decisions. and major political moments—so when Trump shows up at the Knicks’ Finals run. the security changes aren’t happening in a vacuum. The same relationship that Dolan publicly frames as friendship has become a practical storyline for who will be in the building. what logistics will follow. and what some fans will have to navigate.
For now, the focus remains on what happens inside Madison Square Garden on June 8. Trump is expected to be present for Game 3, with extra security precautions affecting some fans, and he has also raised the possibility of attending Game 4 thanks to his relationship with Dolan.
James Dolan Donald Trump Madison Square Garden Knicks NBA Finals campaign donations Mar-a-Lago Adam Silver Penn Station renovation Rockettes security