Confidence Man

1. Trump's Rise: A Blend of Bravado and Calculated Moves

Even without embellishment, there was plenty of power for Trump to soak up that day.

Early ambition. From a young age, Donald Trump aspired to be a star, a desire that shaped his approach to business and politics. He learned from his father, Fred Trump, the importance of cutting corners, making political connections, and treating the government as a tool for personal gain.

Embellishing the narrative. Trump often embellished stories to cast himself in a more favorable light, demonstrating a willingness to distort reality to suit his ambitions. His version of the Verrazano-Narrows Bridge dedication ceremony, for example, was a confection of half-truths and outright falsehoods.

Show business in real estate. Trump brought a showman's flair to the real estate business, conceiving of excessively grand projects and winning press for both completed and uncompleted ventures. This blend of ambition and artifice became a hallmark of his career.

2. Cohn's Influence: Emotional Terrorism as a Strategy

A central lesson Trump would take from his mentor was that literally everything could be treated as a transaction.

Cohn as mentor. Roy Cohn, a lawyer known for his ruthlessness and connections, became a key figure in Trump's life, teaching him how to navigate the complex world of New York power. Cohn's influence extended beyond legal matters, shaping Trump's approach to conflict and negotiation.

Emotional terrorism. Cohn's singular talent was for emotional terrorism, using intimidation and aggression to achieve his goals. This approach, combined with a disregard for rules and regulations, became a defining characteristic of Trump's behavior.

Everything is a transaction. Cohn taught Trump that everything could be treated as a transaction, even seemingly neutral roles like that of an attorney. This transactional view of relationships and power would inform Trump's approach to politics and governance.

3. Navigating New York: Power, Politics, and Profit

For a businessman like Trump, trying to win public backing for his projects at a moment of intense vulnerability for New York, the cynical epithet Fear City would prove more useful.

Exploiting vulnerability. Trump capitalized on New York City's fiscal crisis in the 1970s, using his connections and aggressive tactics to secure tax breaks and approvals for his projects. He was adept at charming and threatening public officials to get what he wanted.

Political connections. Trump understood the importance of political connections in New York real estate, cultivating relationships with figures like Abe Beame and Stanley Friedman. These connections helped him navigate the city's complex bureaucracy and secure favorable deals.

The Commodore deal. Trump's transformation of the Commodore Hotel into a Grand Hyatt showcased his ability to leverage government assistance and political connections to achieve his goals. The deal delivered him forty-two years of property tax relief.

4. Race, Fear, and the City: Trump's Divisive Tactics

Trump was very comfortable navigating the changing waters.

Racial tensions. Trump emerged from a New York City rife with racial tensions, where tribal politics dominated aspects of public life. He capitalized on these divisions, using them to fuel his rise and advance his agenda.

The Central Park Five. Trump's response to the Central Park Five case, in which he called for the death penalty for the wrongly accused Black teenagers, exemplified his willingness to exploit racial fears for personal gain. He never apologized, even after the men were exonerated.

Limited interactions. Trump had few meaningful interactions with people of color, save for those who succeeded in entertainment or sports. His views on race were often shaped by stereotypes and a transactional approach to ethnic and racial groups.

5. The Apprentice: From Real Estate to Reality TV Star

A quarter century later, Trump experienced the ultimate high: in the White House, he received as much attention as the world can offer a single human being.

Obsession with fame. Trump's lifelong desire to be a star led him to pursue opportunities in show business, even as he built a career in real estate. He understood the power of media attention and cultivated relationships with journalists and public relations executives.

The Art of the Deal. The publication of The Art of the Deal elevated Trump from a local developer to a national symbol of success. The book became a bestseller and helped him cultivate an image as a business genius.

The Apprentice. Trump's role as the take-charge billionaire on The Apprentice solidified his image as a successful businessman and propelled him to new levels of fame. The show provided him with a platform to showcase his brand and connect with a national audience.

6. The Price of Power: Scandals, Setbacks, and Survival

By any objective measure, Trump had already led a remarkable life by the time he got there.

Housing discrimination suit. Trump's response to the HUD suit set a behavioral template for nearly every fight he faced: defend himself with falsehoods and claim to be the true victim. He countersued the federal government for $100 million.

Financial challenges. Trump faced numerous financial challenges throughout his career, including bankruptcies and government investigations. He often relied on his father's wealth and connections to bail him out of trouble.

Reinventing himself. Trump was adept at reinventing himself just when he approached the brink of personal disaster, often owing to his own behavior. This ability to adapt and survive became a defining characteristic of his career.

7. The 2016 Campaign: Anger, Enemies, and the Media

A core tenet of the Trump political movement has been finding publicly acceptable targets to serve as receptacles for preexisting anger.

Capitalizing on anger. Trump found his moment by fueling and benefiting from the collapse of cultural and political identities into one another as the country cleaved along the lines of whom you hate, or who hates you back.

Media as enemy. Republicans’ rejection of the mainstream media intensified during the Obama presidency and then dovetailed with Trump’s anger, except for him it was all more personal than it was to his copartisans.

Testing limits. The 2016 campaign was shaped by Trump's impulse for control, his drive to test the limits of transgressive behavior, and his dangerous disregard for democracy and civil rights. He treated the country like a version of New York City’s five boroughs.

8. Presidential Reality: Limited Power, Endless Grievances

Most of the powers that come with the presidency did not actually interest him; he alternated between unfocused involvement in minutiae and appearing to pass the time.

Disinterest in governing. Trump discovered that the powers of the presidency were not commensurate with the grand title. He alternated between unfocused involvement in minutiae and appearing to pass the time.

Recreating his world. Without understanding how the federal government worked, and with little interest in learning, he recreated around him the world that had shaped him. He treated the country like a version of New York City’s five boroughs.

Old models and rivalries. Trump was guided by old models, such as Norman Vincent Peale and George Steinbrenner, and motivated by dated rivalries and grudges. He constantly dragged a deep raft of old grievances into the present.

9. The Aftermath: Defiance, Division, and a Lingering Legacy

After he left office, some of his closest aides and supporters privately described themselves and his political movement as having been held hostage to his refusal to cede the stage.

Refusal to concede. When eighty-one million voters rejected him, revoking the job that brought the most sustained attention he had ever experienced, Trump attacked the democratic processes that brought him to power in the first place.

Scorched-earth strategy. Trump pursued a scorched-earth strategy even as his private actions after the election conceded the bleak reality of his situation. He encouraged his supporters to march to a branch of the federal government that was beyond his control.

Hostage to his refusal. Some of Trump's closest aides and supporters privately described themselves and his political movement as having been held hostage to his refusal to cede the stage. The only thing that would change the situation was Trump’s passing.

Last updated: April 16, 2025