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The last time the New York Knicks played in the NBA Finals, Donald Trump was a Manhattan real estate mogul sitting courtside at Madison Square Garden. Twenty-seven years later, the stage remains the same, but Trump now returns as President of the United States with plans to attend one of the biggest basketball games New York has hosted in decades.

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“I think I’ll be going to one of the games,” Trump told reporters at the White House on Wednesday while discussing the Knicks’ historic Finals run. The president added that he had been invited by “numerous people,” including Madison Square Garden executive chairman and Knicks owner James Dolan.

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If Trump ultimately appears at MSG during the NBA Finals, he would become the first sitting U.S. president ever to attend a Finals game in person. The possibility comes after the Knicks clinched their first Finals berth since 1999 behind an 11-game postseason winning streak that has turned Madison Square Garden into the center of the sports world once again.

Trump’s connection to the Knicks and Madison Square Garden stretches back decades. During the franchise’s 1990s peak, he was regularly photographed courtside at MSG and remained a visible figure around New York sports culture long before entering politics. In November 2014, Trump attended a Knicks-Cavaliers game alongside conservative commentator Bill O’Reilly, while his broader sports appearances have continued throughout his second term in office.

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During an appearance on TalkRadio 77 WABC’s Sid & Friends in the Morning, Trump publicly reaffirmed his support for the franchise while praising Dolan’s stewardship of the team.

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“Well, I am [still a fan of the Knicks], and I get along with Jim Dolan,” Trump said. “I think he’s a really nice guy, and he’s entitled to a good team because he’s suffered a little bit. And boy, some of these players have turned out to be dominant players.”

Trump doubled down on that support again during a Cabinet meeting on Wednesday, calling Dolan a “great guy” who was “having a good year” as the Knicks pushed deeper into the postseason.

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If the Knicks finish the job, they would end a 53-year championship drought dating back to Willis Reed and Walt Frazier’s 1973 title-winning team.

A championship would also create another fascinating political subplot. No NBA champion has visited the White House during Trump’s time in office, with recent teams either declining invitations or citing scheduling conflicts.

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Last season’s champion Oklahoma City Thunder cited “timing issues” for skipping a White House visit, while an anonymous player poll conducted by The Athletic earlier this year showed players nearly split on whether they would accept an invitation if they won the title.

The Real Estate Battle That Strengthened Trump and Dolan’s Relationship

Trump’s growing visibility around the Knicks arrives just weeks after his administration helped settle one of the most politically charged infrastructure fights in New York City. Penn Station’s massive $8 billion redevelopment initially included proposals to relocate Madison Square Garden away from its current footprint above the transit hub.

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Last month, Ramsey Khalifeh, a WNYC reporter, said, “Trump was presented a plan that would move MSG across the streets, And those sources say that Trump’s main comment was, ‘Look, I won’t take this plan seriously unless I’m convinced that James Dolan, who owns Madison Square Garden, would actually move.”

Dolan had resisted relocation efforts for years and again pushed aggressively to keep the arena exactly where it stands. “The decision about whether to move MSG weighed heavily on James Dolan, the billionaire owner of the Garden and the New York Knicks,” reported the US Sun. “Any plan to move forward with a relocation required the owner of the red-hot Knicks’ approval to do so, which he repeatedly shot down.”

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The relocation proposal was ultimately abandoned in May, with the Trump administration backing a redevelopment plan that keeps MSG in place while modernizing Penn Station around it. Under the approved design, the arena will receive a new “classic look” exterior while the broader transit overhaul moves forward.

For Knicks fans, the outcome preserved more than just a building. As the franchise prepares for its first Finals appearance since 1999, Madison Square Garden will remain the center of New York basketball’s biggest moment in nearly three decades.

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Pranav Kotai

3,014 Articles

Pranav Kotai is an editor at EssentiallySports, specializing in basketball coverage with a focus on trade dynamics and front-office decision-making. Having previously worked on the Trade Desk vertical, he brought clarity to how salary cap pressures and roster needs shape NBA transactions. His insightful coverage of the Philadelphia 76ers’ decision to hold firm on Joel Embiid amid trade speculation highlights how market context and team strategy influence major roster moves. Before joining EssentiallySports, Pranav holds experience of skills in professional writing, editorial work, and digital content creation. He holds a postgraduate diploma in digital media from a reputed institute, where he mastered the tools to create engaging and credible content across various platforms. Known for his attention to detail, proficiency in storytelling, and editorial expertise, Pranav combines deep basketball knowledge with sharp analytical abilities to deliver clear, insightful perspectives on the complexities of NBA trades and team management.

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