In 1999, President Bill Clinton stood across the street from New York’s Pennsylvania Station with the state’s governor and its senior senator to announce plans for transforming the area into a modern gateway for the nation’s biggest city.

Presidents do not often appear at news conferences about train stations. But Penn Station, in Midtown Manhattan, was the busiest transportation hub in North America, and Mr. Clinton had made public transit a priority. He and Gov. George E. Pataki posed beside a miniature model of a grand new train hall, while Senator Daniel P. Moynihan extolled its future grandeur.

“Penn Station is the start,” Mr. Moynihan said, “and we will find — when we complete this project — that suddenly all will seem possible.”

More than 25 years, five presidencies and four governors later, the plan to rebuild Penn Station is nowhere near completion.

For the 600,000 people who pass through every day, Penn Station is indispensable. It remains the busiest transit hub in the United States, with nearly double the number of daily passengers as the busiest airport, Hartsfield-Jackson Atlanta International. Much of the Eastern Seaboard might grind to a halt without it.

It is also widely abhorred. Passengers descend into a gloomy, dimly lit warren of overcrowded concourses, much of it layered in grime and corroded by decay, sitting above an array of subterranean tracks whose age creates regular snarls and delays that cost New York millions of dollars in lost productivity each day.

More broadly, it is a stagnant symbol of something deeper in America, a condition that afflicts so many attempts to get big things done: inertia. Again and again, when America undertakes big projects, politics and government get in the way.

Countless ideas for making Penn Station grander and more commuter-friendly have been floated and shelved over the decades. The conversion of the James A. Farley Building across Eighth Avenue into Moynihan Hall for passengers was an exception, if one that ran wildly over budget and beyond schedule. But Moynihan, named for the senator, is mostly ornamental. With each attempt to restart work on the larger underground station, progress has been torpedoed by a political rivalry or a powerful billionaire or infighting among transit agencies with their own priorities.

As yardsticks of American progress go, Penn Station does not inspire pride. Since Mr. Clinton’s appearance there 26 years ago, China has constructed nearly 30,000 miles of high-speed rail tracks and built more than a thousand new stations.

There have been other bright spots, such as the renovation of LaGuardia Airport in New York. But that took more than eight years. Saudi Arabia built an entire transit system in Riyadh in a little over 10 years.

In the United States, the investment of billions of dollars in taxpayer money and the extraordinary undertaking of renovating century-old infrastructure are among the many reasons large projects stall before they even get off the ground.

But the failure often starts and stops with politics. Some critics blame multiple layers of federal, state and local regulations that deter investment. Some blame a progressive inclination to spread authority to community groups and individuals. Others point to extreme partisan politics as the root of the paralysis.

“We’ve got a system that doesn’t have anyone who can actually make the decision,” said Marc J. Dunkelman, a research fellow at Brown University and the author of “Why Nothing Works.” The stasis at Penn Station is a “microcosm of why generally government doesn’t work,” he said.

Eliot Spitzer, a former Democratic governor of New York, said Penn Station was “a classic example” of how “fractured decision-making” leads to delays and conflicting priorities.

“When you have that many entities involved, it makes it nearly impossible to get a resolution,” he said.

Penn has long been a station divided, carved up into fiefs occupied and maintained by railroads whose managers constantly compete for authority and resources.

The tension among those three agencies has been compounded by the intransigence of James L. Dolan, the billionaire whose company owns Madison Square Garden, which has squatted atop the station for more than 60 years. Their failure to collaborate on a solution has left Penn mired in a sorry state that has been lamented by a generation of everyday commuters.

In New York, a long line of strong-willed elected officials — Mr. Spitzer included — have pledged that a makeover of Penn Station was on the way.

In 2006, Mr. Pataki, the Republican governor, spoke of creating “a visionary new Pennsylvania Station.” His successor, Mr. Spitzer, said in 2008 that he was committed to a revamp of Penn that would “redefine Midtown Manhattan.” In 2016, Gov. Andrew M. Cuomo likened the station to “seven levels of hell” and, rolling out his own $3 billion plan, vowed, “This will get done.”

Most recently, the current governor, Kathy Hochul, said that “New Yorkers do not deserve what they have been subjected to for decades at Penn Station” and presented a revised version of Mr. Cuomo’s proposal with an estimated cost of more than $6 billion.

After all of that talk about all of those visions, Penn Station remains a confusing, overburdened labyrinth of hallways and stairwells buried beneath a 20,000-seat entertainment venue.

Its century-old infrastructure takes frequent bites out of the metropolitan economy: Every hour of delay for commuters from Long Island or New Jersey costs the city’s employers nearly $20 million, according to an inflation-adjusted estimate from the Partnership for New York City, a business group.

Kathryn S. Wylde, chief executive of the partnership, said in 2017 that “Penn Station is a symbol of the failure of America to keep up with the escalating demands on urban public transportation.”

She reiterated that sentiment in September: “Nothing has changed.”

Community advocates agree. “We really do have a tragic level of institutional dysfunction with warring entities,” said Lynn Ellsworth, who in 2020 co-founded the Empire Station Coalition, which called for a redesign that would render Penn Station more efficient, more welcoming and easier to navigate.

The railroads that coexist within the station, Ms. Ellsworth said, “don’t have the managerial competence to rise above their parochial self-interests.”

Penn Station is a layer cake of inadequacy, with three levels that complicate all efforts to improve service for the thousands of people passing through every day.

New York officials have frequently likened a trip through Penn to a descent into hell. Andy Byford, the Amtrak executive recently put in charge of overhauling the station, described the platforms as a “dark, gloomy, boiling-hot, narrow and cramped situation.”

Right now, Amtrak is focused on the construction of a new two-track rail tunnel under the Hudson River, a $16 billion project known as Gateway. (This fall, the Trump administration suspended federal funding for the project and threatened to terminate it in an apparent attempt to pressure Democrats amid a government shutdown.)

The Gateway project would significantly increase train capacity across the Hudson and would require big changes at Penn Station.

The Garden’s owners, who own the air rights for any development above the station, have resisted recent attempts to arrange the arena’s relocation. In 2023, city officials renewed the Garden’s operating permit for an additional five years.

At the time, Mr. Dolan, the chairman of MSG Entertainment, said in an interview: “Another five years and there’ll be some changes in the political structure and we’ll go at it again. Nothing is going to happen.”

In that 2023 interview, Mr. Dolan expressed doubt that the station’s stakeholders would agree on a comprehensive plan to improve it any time soon.

“We never get to the finish line, and it’s because of all the politicking and bureaucracy and because of all the different constituencies,” he said. “I mean, there’s New Jersey Transit, there’s Amtrak, there’s the M.T.A., there’s the governor’s office, there’s the city. And everybody has to say yes. And everybody’s got a stick in the fire.”

The roots of all this dysfunction can be traced back more than a century.

In 1901, Alexander J. Cassatt, the president of the Pennsylvania Railroad, was a frustrated train traveler. To get from Philadelphia to New York City, he had to transfer at his company’s easternmost terminal in Jersey City to a ferry that would carry him the last mile across the Hudson River.

At the time, the country’s rail system was a robust collection of independent companies vying for prominence on the most popular routes. Collaboration was never in their DNA.

His railroad’s main rival, the New York Central Railroad, had already built itself a terminal in the heart of Manhattan, which later became Grand Central Terminal. Mr. Cassatt burned for a competitive foothold in the nation’s largest city.

“We must find a way to cross,” he said, according to “Conquering Gotham,” a 2007 book by Jill Jonnes.

Within 10 years, Mr. Cassatt’s company had completed the unprecedented feat of digging a tunnel under the Hudson to connect to a station it had created west of Seventh Avenue in Midtown: the new Pennsylvania Station.

The Pennsylvania Railroad, commonly known as the Pennsy, declared that the station would have “the character of a monumental gateway and entrance to a great metropolis.”

Originally, Penn Station was the province of the Pennsy’s intercity trains and Long Island Rail Road commuter service.

That centralized control could have continued after the mid-1960s if not for one critical error, said Mitchell Moss, a professor of urban policy and planning at New York University.

In 1965, Gov. Nelson A. Rockefeller had New York buy the struggling L.I.R.R. for $65 million and created the Metropolitan Transportation Authority to manage it. William J. Ronan, the man Mr. Rockefeller hired to run the authority, told Mr. Moss that Rockefeller had passed up the opportunity to also acquire Penn Station for a price that would seem like a screaming bargain today, Mr. Moss recounted.

“He felt that was a terrific mistake,” Mr. Moss said, recalling their conversation at the Everglades Club in Palm Beach, Fla., about 12 years ago.

“The fundamental original sin was not buying Penn Station,” said Mr. Moss, a critic of how Amtrak has managed the station. “That’s the key error, and that has created a lack of clarity about who controls Penn Station.”

Instead, the M.T.A. wound up as a tenant of Amtrak, the federal corporation that inherited many of the Pennsy’s assets after a 1970 bankruptcy.

Like NJ Transit, the L.I.R.R., the busiest commuter railroad in the country, has carved out its own separate and unequal territory within Penn Station.

The dividing lines are clear, at least to those who understand the station’s entrenched rules of engagement, as Janno Lieber, the chairman of the M.T.A., does.

Standing beneath a tangle of exposed pipes and wires in a corridor known as the Hilton Passageway, Mr. Lieber explained that each of the railroads is responsible for maintaining its own turf, including the platforms and tracks that only it can use.

North of the passageway, his agency handles the waxing of the floors and the cleaning of the restrooms. Its police force patrols the concourses.

South of the passageway, those burdens fall on NJ Transit, a perennially struggling state-run corporation. Its workers, clad in fluorescent green T-shirts, replace lightbulbs and scrub the metal prison-style toilets.

Each railroad has its own dedicated entrance at the front of the station on Seventh Avenue.

NJ Transit’s leads to a waiting area that is cooled by a fleet of large, portable air-conditioners whose exhaust is vented through white ducts that snake up to the ceiling. The cramped area is known to commuters as “the pit” because of how crowded it gets during evening rush hour.

L.I.R.R. customers enter through a broad concourse that was recently widened, brightened and filled with cafes and fast-food shops. Mr. Lieber called it “a much more functional environment” that had come about because the transportation authority chose not to wait for an agreement with the other railroads and, on its own, overhauled just the areas it managed.

“We kind of took control of our destiny and said this can’t go on any longer,” Mr. Lieber said.

Untangling the knot of Penn Station’s shortcomings is a challenge that has long stymied New York’s most powerful elected officials.

In 2005, Gov. Eliot Spitzer came as close as any governor ever has to clearing the way for a more majestic rebuild of Penn Station when Mr. Dolan agreed, in general terms, to the relocation of the Garden across Eighth Avenue.

But the plan met opposition from preservationists. Mr. Dolan wanted to back out, but Mr. Spitzer, who called himself a “bulldozer,” plowed ahead. In March 2008, the two men had a tense meeting that Mr. Dolan later recounted to a New York Times reporter. “He was tough,” Mr. Dolan said of the governor.

A week later, Mr. Spitzer was caught up in a prostitution scandal and resigned. By the end of the month, Mr. Dolan’s company announced that the Garden was “not moving,” effectively killing any hopes for Mr. Spitzer’s plan.

Several years passed before another brash Democratic governor, Andrew M. Cuomo, took on the challenge of fixing Penn Station — without trying to move the Garden.

In 2016, Mr. Cuomo unveiled a $3 billion plan to “dramatically renovate” Penn Station, starting with a long-stalled idea to convert the neighboring Farley Building, which had been the General Post Office, into a train hall that would serve as an annex for Penn.

That idea, first broached by Senator Moynihan, had “languished because of a lack of financing, political inertia, squabbles with transportation agencies and the developers’ ambitions,” The Times reported in early 2009.

Mr. Cuomo’s plan centered on a partnership between the state and two of the country’s biggest developers, Related Companies and Vornado.

The governor became intensely involved, even threatening at one point to replace the private partners because they were not moving fast enough. He drove that project over the finish line at the end of 2020, more than 25 years after it was first proposed.

“Moynihan is a really good Phase One; it’s the appetizer,” said Vishaan Chakrabarti, a New York architect who has been calling for a radical overhaul of Penn Station since 2016. “But the main station in the subbasement of the Garden is the entree.”

Transportation experts give credit to Mr. Cuomo, who resigned as governor in 2021 amid sexual harassment allegations and ran unsuccessfully for mayor this year, for applying his famously abrasive personality to get Moynihan Train Hall finished.

But they also note that the project was much less costly and less complicated than renovating Penn Station. New Jersey had little say in the design of Moynihan, and the fact that many NJ Transit trains are accessible from its glass-roofed hall goes virtually unmentioned inside the building.

As soon as Kathy Hochul succeeded Mr. Cuomo, she made improving Penn Station a priority. Within months of taking office, she stood at a lectern in the station and promised it would be transformed from a “hellhole” into a world-class transit hub.

The M.T.A., which the governor controls, would take the lead on managing a rebuilding plan with an estimated cost of close to $7 billion, she said. Amtrak and NJ Transit accepted supporting roles in the planning.

“It’s going to right the wrongs of the past,” Ms. Hochul said. “It’s going to jump-start something that should have been done a long time ago.”

Ms. Hochul indicated that the state was open to suggestions for how Penn should be improved, and proposals began to roll in. A private developer, ASTM North America, teamed up with Mr. Chakrabarti’s studio, PAU, to propose a design that would require the acquisition and removal of a theater attached to the Garden along Eighth Avenue. Amtrak officials supported the concept, but Mr. Lieber rejected the idea of paying a large sum to Mr. Dolan’s company.

Other architects put forward different ways of renovating the station. Some revived the idea of building a new home for the Garden nearby. Others centered on reorganizing the region’s rail service so that Penn would not have to be expanded at all.

All of them awaited word from New York officials about how and when the project would get rolling.

After Donald J. Trump was elected president again last November, Ms. Hochul asked him to have the federal government cover most of the cost of a new station, she said. She even floated the idea that it could be renamed after him.

Rather than bankrolling New York’s plan, the Trump administration announced this spring that it had lost faith in the state’s ability to manage the project and reassigned it to Amtrak. Sean P. Duffy, the transportation secretary, appointed Mr. Byford, who earned the nickname “Train Daddy” when he oversaw the city’s subway system from 2018 to early 2020, to take charge of the “transformation” of Penn Station.

Some advocates of the renovation said they worried that Mr. Trump’s involvement would set the project back to square one. But others said that having decision-making power concentrated in a president who sees himself as a builder might be the best recipe for a better Penn.

“He just took over Penn Station,” Mr. Cuomo said in a recent interview. “The M.T.A. was working on it for years and had a whole plan.” The former governor added that he expected that Penn was “going to wind up being Trump Station, in the heart of Manhattan.”

Ms. Hochul responded to the federal intercession by withdrawing New York’s financial commitment.

In a recent interview, Ms. Hochul said she was not abandoning the project. “I’m just happy that I don’t have to put money in it,” she said.

Recounting a conversation with Mr. Trump, she said she had pointed out that Amtrak owned the station. “Why should we have to pay for a building that’s owned by this other entity?” Ms. Hochul said she had asked Mr. Trump.

Still, she told the president: “We have the possibility of getting this underway before you leave office. Let’s make that our goal,” she recalled. “He agreed.”

Now the future of Penn Station rests with Mr. Byford, who said he had been told to get construction started before the end of 2027. He laid out an accelerated schedule that included a solicitation of bids from private companies that want to serve as the project’s master developer. Amtrak will make a decision by May 2026, he said.

Mr. Byford said the bidding would be “an open and fair competition with no preconceived notions of the outcome, but it will be conducted to a very aggressive timeline.”

He said Amtrak’s longstanding plan to expand the station by taking over all or part of a neighboring block of Midtown was “on hold” to focus attention on the makeover. In the meantime, he said, federal transportation officials will study whether having commuter trains pass through Penn and continue on to stations outside the city instead of turning around — a practice known as through-running — could accommodate projected growth in rail traffic in the region.

Ms. Ellsworth, a proponent of running the L.I.R.R. and NJ Transit trains through the city and into each other’s territory, said she had been calling for the federal government to put an end to the infighting and red tape that had thwarted all hopes for an improved station.

“We need a parent to come in here and knock heads between the various entities,” she said.

Mr. Dunkelman of Brown University was skeptical that “you’re somehow going to bring in a czar who can wrangle all the separate interests.”

“Maybe the Train Daddy will figure it out and get it done, but the fundamental issue here is not one of personality or incompetence,” he said. “It’s a political octopus built to fail.”