President Donald Trump said he’d take a plan to rebuild Penn Station and relocate Madison Square Garden seriously if the arena’s influential owner is willing to play ball, according to sources familiar with the talks.
A delegation of politically connected Trump supporters floated the plan during a closed-door Oval Office meeting in September that has not been previously reported. If approved, their proposal would transform Midtown by moving the Garden from its location atop Penn Station, which serves 600,000 daily riders.
The meeting took place months before Amtrak, which owns the massive transit hub, announced the nonprofit’s plan as one of three finalists for the station’s overhaul.
The meeting and decision to move the proposal forward signal the president is considering the option to move the storied arena, according to four sources who have knowledge of the Oval Office meeting but asked not to be named because they were not permitted to disclose details.
The group represented the Grand Penn Community Alliance, a nonprofit financed by wealthy conservative donor Thomas Klingenstein. The attendees told the president their proposal would restore the station to its former glory, before it was torn down in the 1960s to make way for the Garden, the sources said.
The proposal, made public last March, would redesign the train hall’s entrances with Greco-Roman columns, install a large clock and deck the space with a glass roof that lets in natural light.
Under the nonprofit’s proposal, the arena’s current site would be replaced by a fountain and green lawn between the new Penn and Moynihan Train Hall. The 19,000-seat arena would move across Seventh Avenue.
A public plaza would be put in place of Madison Square Garden under the proposal from the Grand Penn Community Alliance.
Courtesy Grand Penn Community Alliance
The sources said Trump was well aware the plan couldn’t move forward without approval from James Dolan, the billionaire owner of the Garden and New York Knicks, who has for years publicly refused to relocate. But the president didn’t write off the idea, the sources said.
The sit-down is an example of the behind-the-scenes campaign taking place ahead of the selection of a “master developer” for Penn Station. Amtrak said a winner will be picked in May. While the Grand Penn plan is the only one that proposes moving the Garden, federal transportation officials say they expect to invest billions into the project.
Trump, who made his name in Manhattan real estate, is widely thought to be fixated on leaving a legacy far beyond his second term. Last year, his administration seized control of the Penn Station rebuild from the MTA, turning the project over to Amtrak and the U.S. Department of Transportation.
One of the sources close to the process said everyone involved with the project understands that the president will make the final decision.
White House spokesperson Kush Desai said that “as a New York native, President Trump is personally invested in revitalizing New York Penn Station.”
A historic plan, shrouded in secrecy
Because the groups behind the three competing Penn Station plans have all agreed to a gag order imposed by Amtrak, there have been few public details about the process for the multibillion-dollar project. The finalists were announced in January, but the overall secrecy has left politicians representing the area uneasy.
U.S. Rep. Jerry Nadler was among several elected officials who sent a March 16 letter to Andy Byford, who’s leading the project for Amtrak, criticizing the lack of transparency. The letter requested a memo “identifying the specific legal basis, if any, for withholding the RFP [request for proposals] from public disclosure.”
Penn Station has lacked natural light since the 1960s, when it was buried beneath the Garden.
Stephen Nessen / Gothamist
Nadler said he’s concerned about how the selection of such an important plan would be made, and questioned the objectivity of the procurement process.
“We don’t know how it’s going to be financed … President Trump is involved and maybe he’ll select the winning bidder. On what criteria? We don’t know,” Nadler said. “What are the criteria for selecting the winning proposals? How much money you gave to the Trump campaign?”
“The whole thing is secret,” he said.
U.S. DOT spokesperson Danna Almeida said, “Amtrak has a strong, objective and detailed rubric that will score each proposal on their own merits to determine the Master Developer” for Penn Station. She added that “procurement and legal rules allow the firms to meet with the White House.”
The plan to move the Garden is the most ambitious of the three finalists being considered.
According to the Grand Penn Community Alliance, the plan comes with an estimated price tag of $7.5 billion, which includes the cost of moving the Garden.
Amtrak officials previously told finalists the station will be rebuilt using a “public-private partnership.”
That model was used for the redevelopment of LaGuardia Airport. Private companies covered the cost of construction and, in exchange, control revenues from concessions at the terminals.
Klingenstein, a conservative hedge fund manager and chair of the Clairemont Institute, an influential right-wing think tank, said in an interview at his Upper West Side apartment that he spent $4 million on the Grand Penn plan.
Federal election filings show he donated more than $13 million to Trump and other Republicans during the 2024 election cycle.
Klingenstein noted there were three other “Madison Square Gardens,” each at a different location in Manhattan. The previous incarnation was at 50th Street and Eighth Avenue.
“The name is iconic,” said Klingenstein. “This one doesn’t stand out. In fact, it’s a little bit bland. It’s old.”
“I think Dolan would want to turn a new Garden into something like his Sphere,” he speculated.
Renderings of the Grand Penn plan show a new Madison Square Garden wrapped in a large digital screen, similar to Dolan’s state-of-the-art Sphere in Las Vegas.
Dolan’s view of the redevelopment of Penn Station remains unclear. Representatives for Madison Square Garden did not respond to multiple requests for comment.
The Grand Penn Community Alliance envisions a brand new Madison Square Garden on the other side of Seventh Avenue from the current venue.
Courtesy Grand Penn Community Alliance
Justin Shubow, the president of a Washington, D.C.-based advocacy group called the National Civic Art Society, is also involved in the project. He helped draft an executive order signed by Trump last year requiring all new federal buildings to be constructed with “the classical architecture of ancient Athens and Rome.”
An Amtrak document guiding the finalists said any proposed design for Penn Station must “be cognizant of” the executive order on architecture that Shubow helped draft.
U.S. Transportation Secretary Sean Duffy appointed Shubow to an infrastructure design council last year. In an interview, Shubow acknowledged Grand Penn Community Alliance had ties to the Trump administration.
“We certainly have some advantages. Admittedly, it seems that other master developers… also have a lot of power and influence,” Shubow said of the Grand Penn plan. “This is a huge multibillion-dollar project and I would expect all the parties involved to have aces up their sleeves.”
Justin Shubow helped draft an executive order signed by President Donald Trump last year that mandates “classical” architecture for new federal buildings.
Ramsey Khalifeh / Gothamist
The Grand Penn plan was submitted by Grand Penn Partners, a business venture that’s technically separate from the nonprofit Grand Penn Community Alliance, even though they’re pitching the same design. A White House spokesperson said the nonprofit arm did not violate any rules by lobbying directly to Trump.
Desai, the White House spokesperson, said that “any notion that the president is putting his finger on the scale unfairly is completely baseless.”
Moving MSG
Since the original Penn Station was torn down in the 1960s to build Madison Square Garden, groups have called for the arena to be moved so the transit hub can be restored to its former glory.
“It was one of the greatest buildings we’ve had in this country, and it’s astonishing that we decided to tear it down,” said Richard Cameron, an architect who worked with Shubow on an earlier plan to restore the original Penn Station. “People think of it as an architectural crime that we wouldn’t have figured out the value of that building before destroying it is just extraordinary.”
The Grand Penn Community Alliance wants Madison Square Garden to move across the street to an empty lot where the Hotel Pennsylvania once stood.
Stephen Nessen / Gothamist
Now, the people behind Grand Penn Alliance see a once-in-a-generation opportunity to revitalize the notoriously dreary and labyrinthine station.
They want Dolan to build a new arena on the east side of Seventh Avenue between West 32nd and 33rd streets — potentially with taxpayer subsidies — atop the former site of the Hotel Pennsylvania, which was demolished in 2023.
That lot is owned by real estate giant Vornado, which owns the bulk of the land around Penn Station. The company is also a partner in a competing proposal vying to run the Penn Station project that was first pitched in 2022 by the construction company Halmar. That plan would rebuild the exterior of the Garden, as well as add a new entrance on Eighth Avenue. The ceilings in Penn Station would be heightened. New skylights and windows would let in natural light.
Like Klingenstein, Vornado CEO Steven Roth also has ties to Trump. He has done business with the president on real estate ventures, including purchasing office towers in New York and San Francisco. Vornado did not respond to a request for comment.
A Penn Station plan backed by Halmar and Vornado would leave Madison Square Garden in place.
Courtesy ASTM
The third proposal comes from a group called Penn Forward Now, which is backed by Canadian finance management company Fengate. That pitch has not yet been made public. Representatives for the project declined to comment, citing Amtrak’s order not to speak to the press. One of the sources familiar with the proposals said the Penn Forward Now would also leave the Garden in place.
New York City officials have recently mulled allowing the arena’s operating permit to expire, forcing a move. The Garden’s location above Penn Station has for decades hindered plans to overhaul the train hub, in part because the columns supporting the arena sink into its platforms.
Dolan has publicly rejected the notion of moving the Garden, which is marketed as “the world’s most famous arena.”
“No, I’m not going to move Madison Square Garden,” Dolan said in an interview with FOX5 New York in January 2023, the last time the permit was up for renewal.
The Garden’s operating permit expires in 2028.
The columns supporting Madison Square Garden sink down onto the platforms and tracks at Penn Station.
Stephen Nessen / Gothamist
Dan Garodnick, the former head of city planning, who oversaw the most recent permit extension, said moving the venue would come with a huge price tag.
“Everything would be better if Madison Square Garden was not physically located on top of one of the region’s most important transit centers,” said Garodnick. “This is a complicated proposition. Not only does the Garden need a plan to go, but there are significant costs to moving it and perhaps disruptions to its operations for a period of time. Nobody is moving a massive check [right now.]”
New sports arenas typically come with major controversy as billionaire team owners seek taxpayer subsidies for the project. Gov. Kathy Hochul faced criticism in 2022 when she pushed through $850 million in taxpayer money for a new Buffalo Bills stadium.
And Madison Square Garden already gets a good deal from taxpayers: The venue is exempt from paying property taxes due to legislation approved by state lawmakers in 1982.
Almeida, the federal transportation spokesperson, said the Trump administration is prepared to invest a tremendous sum into the project.
“The federal government will invest billions in taxpayer dollars to revitalize New York Penn Station and has a strong interest in ensuring it meets the American people’s expectations,” Almeida wrote in a statement.
Trump administration officials — as well as Klingenstein — have floated renaming a rebuilt Penn Station as “Trump Station.”
Trump donor Thomas Klingenstein believes classical architecutre embodies conservative values.
Ramsey Khalifeh / Gothamist
Klingenstein said his proposal for the new train station would evoke conservative values.
“We [conservatives] believe in such a thing as great men, which liberals tend not to,” he said. “So I think there’s a natural connection between classical architecture and conservatism, and I think it makes sense for Trump, who’s trying to Make America Great Again. He, too, is looking backwards.”
Klingenstein’s office is filled with memorabilia honoring other people he considers “great men,” like Abraham Lincoln and Frederick Douglass. He said Trump should be held in the same regard.
“This is the kind of thing that not only would Trump want to put his name on it, but should put his name on it,” he said. “If it comes to pass, it will be an example of one man — because Trump is the only one who can make this happen — doing a great thing.”
