After his daily criminal trial proceedings come to a close, Donald J. Trump typically retreats to the lavish triplex atop Trump Tower, the iconic high-rise he constructed in the early 1980s to establish himself as a prominent builder.
Returning to Manhattan for an extended period since his move to Washington in 2017, Trump spends his days in a dreary downtown courtroom facing 34 felony charges, listening to individuals from his past describe him as a deceitful liar who tarnished the White House. The looming possibility of imprisonment hangs over him.
Nevertheless, those close to him say that in the evenings, he relishes being back in the penthouse apartment that has been his home for four decades. It serves as a constant reminder of a time he considers to be the easiest period of his life.
This period marked the era of “greed is good,” during which Trump portrayed himself as a national industry titan despite his relatively modest real estate holdings. He had just completed the construction of a gleaming tower on Fifth Avenue, which stirred controversy among elites and led to his demand for a tax break from the city. Trump frequently references this era, alluding to 1980s cultural icons like the news program “60 Minutes,” Time magazine, and personalities such as boxer Mike Tyson.
However, this was also the period when Trump’s public image began to crumble. The decade concluded with a heated tabloid feud between him and his first wife, Ivana, with investigative stories exposing his financial struggles and reliance on his father’s assistance. It was during the ’80s that Trump oscillated between seeking acceptance from elites and rebelling against them, exemplified by his decision to destroy Art Deco friezes atop a building he demolished to erect Trump Tower.
Despite claims of disdain from the city’s power players, Trump found some acceptance and support among them. With the help of his father’s connections in Brooklyn’s political circles, he forged relationships with influential figures like publishing magnate S.I. Newhouse and frequented the stadium box of Yankees owner George Steinbrenner.
Trump also cultivated a lasting bond with Manhattan district attorney Robert Morgenthau, a connection that provided him with a sense of security, according to former Trump Organization employees. Trump has asserted that Morgenthau would have never allowed the charges brought against him.
Andrew Stein, former City Council president, remarked, “It’s absolutely true — that was his golden time, no question.” Trump’s presidency, characterized by navigating unfamiliar rules and laws in a resistant establishment, failed to bring him the same satisfaction he experienced holding court at Manhattan’s 21 Club.
The ongoing trial sheds light on aspects of Trump’s character that became evident in the following decade, the 1990s, beyond the facade created by his ghostwritten book “The Art of the Deal” in 1987. The courtroom proceedings reveal his proclivity for retaliation, reliance on fixers, desire to be seen as a playboy, and his unconventional business practices within his family-run company.
Moreover, they underscore the paradox of a man who constructed a persona in the media and on television managing to ascend to the presidency, blurring the lines between reality and fiction under the weight of the Oval Office and a vast government apparatus.
The era that shaped Trump is vividly captured in Tom Wolfe’s “The Bonfire of the Vanities,” where a wealthy banker’s hit-and-run incident in the Bronx amid racial tensions mirrors the societal complexities of the time. This echoes the atmosphere in the courtroom where Trump now spends most of his days, under the harsh glare of fluorescent lights and the phrase “In God We Trust” looming over Justice Juan M. Merchan.
Some days, Trump criticizes his lawyers and privately laments the absence of a figure like Roy M. Cohn, his former fixer and mentor. Similarly born into privilege in the outer boroughs, Cohn played a pivotal role in Trump’s life, teaching him to deny wrongdoing, attack his adversaries, and seek lawyers willing to go to any lengths to defend him.
While Trump initially distanced himself from Cohn as the 1980s began, he later revered him as an ideal for his subsequent legal counsel in Washington.
Mr. Trump eventually distanced himself from Cohn as the latter faced repeated indictments due to illness. Despite Trump’s earlier criticisms, he later idealized Cohn, urging his subsequent lawyers to emulate his mentor’s approach.
During his presidency, Trump seldom returned to Trump Tower, opting for weekends at Mar-a-Lago or Bedminster to avoid Manhattan’s rejection at the ballot box. In 2019, he officially changed his residence to Florida, signaling his detachment from Manhattan’s disapproval. By the end of his term, following the Capitol insurrection, he seemed resigned to prioritizing his own desires over appeasing others.
Recently, the ex-president and presumed Republican nominee has sought to assert his dominance over a city that he left behind, particularly in the post-pandemic era marked by uncertainty.
In a recent rally in the Bronx, Trump addressed a crowd in a predominantly Black and Latino neighborhood, revisiting his past exploits including the construction of Trump Tower. Despite facing challenges, he expressed confidence in his abilities, emphasizing his successful projects such as revitalizing the Wollman Rink in Central Park in the ’80s.
