
Trump
9 minThe Art of the Deal
Introduction
Narrator: An elderly widow in Georgia, Mrs. Hill, was on the verge of losing her family farm. Her husband had taken his own life, hoping the insurance money would settle the farm's debts, but it wasn't enough. The bank was unsympathetic and foreclosure was imminent. Then, a news report about her plight caught the attention of a New York real estate developer. He made a call, not to offer a simple donation, but to confront the bank directly. He threatened legal action and public exposure, forcing the bankers to reconsider. Within an hour, they called back, ready to negotiate. The developer then used his media connections to help raise the remaining funds, and a mortgage-burning ceremony was scheduled for Christmas Eve. This wasn't just a business transaction; it was a display of leverage, media savvy, and aggressive intervention.
This story offers a glimpse into the operational mindset detailed in Donald J. Trump's seminal 1987 book, Trump: The Art of the Deal. Co-authored with Tony Schwartz, the book is not a traditional business manual but a series of high-stakes case studies that reveal a philosophy where deals are an "art form," driven by instinct, ambition, and an unyielding focus on the present moment.
Think Big, But Trust Your Gut
Key Insight 1
Narrator: Trump’s philosophy begins with a simple but powerful premise: "If you’re going to be thinking anyway, you might as well think big." He argues that most people are held back not by a lack of ability, but by a fear of success and the pressure of making significant decisions. However, this ambition is always tempered by a deep reliance on intuition. He describes his deal-making style as loose and imaginative, avoiding rigid structures and plans in favor of instinct.
A defining example of this principle is the oil deal he chose not to make. A trusted friend from Texas presented him with a seemingly perfect opportunity to invest $50 million in a small oil company, promising to double or triple the money within months. On paper, the deal was flawless. Yet, Trump felt a gut-level unease. He was a real estate developer, and the oil industry was foreign territory, lacking the creative element he thrived on. Despite the persuasive pitch and the paperwork being drawn up, he called his friend and backed out. Several months later, oil prices plummeted, the company went bankrupt, and the investors lost everything. Trump’s intuition saved him $50 million, reinforcing a core lesson: sometimes the best and most profitable deals are the ones you walk away from.
The Power of Relentless Persistence
Key Insight 2
Narrator: More often than not, Trump argues, the difference between success and failure is "sheer persistence." Many of his most iconic deals were not quick victories but the result of years of patient, strategic pursuit. The story of acquiring the Bonwit Teller site on Fifth Avenue, which would become the location for Trump Tower, is a masterclass in this approach.
In the mid-1970s, he identified the site as the perfect location for a luxury skyscraper, but the parent company, Genesco, refused to sell. For three years, Trump persistently wrote letters to the company's head, Franklin Jarman, only to be repeatedly rejected. Instead of giving up, he waited. His moment came when he read that Genesco was in financial trouble and had installed a new CEO, John Hanigan, a turnaround artist tasked with selling assets to save the company. Trump immediately seized the opportunity, leveraging his connections to secure a meeting. He negotiated a deal and, crucially, obtained a letter of intent to prevent Genesco from backing out. This persistence was the foundation of the entire project, proving that a "no" is often just a "not right now."
Transform Decay into Gold
Key Insight 3
Narrator: A central theme in Trump's real estate strategy is his ability to see immense potential where others see only decline and decay. He actively sought out undervalued or dilapidated properties in prime locations, confident in his ability to transform them. His first major Manhattan project, the renovation of the Commodore Hotel, perfectly illustrates this vision.
In the mid-1970s, New York City was near bankruptcy, and the area around Grand Central Station was blighted. The Commodore Hotel itself was a failing, rundown property. While his own father warned him that buying it was like "fighting for a seat on the Titanic," Trump saw a prime location with enormous potential. He embarked on a complex, multi-front negotiation. He convinced the city to grant an unprecedented 40-year tax abatement by arguing it was the only way to spur investment. He partnered with Hyatt to bring in hotel management expertise and secured financing from skeptical institutions. The result was the Grand Hyatt, a gleaming, modern hotel that became a symbol of New York's resurgence and revitalized the entire 42nd Street area. It demonstrated his core belief that with vision and bold negotiation, it's possible to turn a liability into a landmark.
Leverage Everything: Media, Politics, and Perception
Key Insight 4
Narrator: For Trump, leverage is not just about money; it's about using every tool available to shape a deal in his favor. This includes the media, political pressure, and public perception. His rebuilding of the Wollman Skating Rink in Central Park is a prime example. For six years, the city had tried and failed to repair the rink, spending over $12 million with no end in sight. The project became a symbol of government incompetence.
Trump saw an opportunity. He publicly offered to take over the project and rebuild the rink in under six months for a fraction of the cost. He used the media to champion his cause, creating a public relations storm that pressured the mayor's office to accept his offer. Once in charge, he completed the project in just three and a half months and $750,000 under budget. The rink became a massive success, and Trump donated the profits to charity. The victory wasn't just in the construction; it was in demonstrating that his private-sector efficiency could succeed where public bureaucracy had failed, a narrative he masterfully controlled through the press.
Controversy Sells
Key Insight 5
Narrator: Throughout the book, Trump acknowledges the power of publicity, subscribing to the idea that "bad publicity is sometimes better than no publicity at all." The demolition of the Bonwit Teller building to make way for Trump Tower provided an unforgettable lesson in this principle. The building featured two large Art Deco sculptures that a museum had expressed interest in preserving.
During demolition, the crew determined that safely removing the heavy sculptures would be prohibitively expensive and cause costly delays. Trump made a swift, bottom-line decision: he ordered them destroyed. The next day, the New York Times ran a front-page photo of the demolition, sparking public outrage and painting him as a developer who prioritized profit over art. While he later expressed regret over the decision, he also noted its paradoxical effect. The controversy generated enormous, worldwide attention for the Trump Tower project. The building was suddenly famous, and this notoriety, he claims, led to a significant upsurge in apartment sales. It was a stark lesson that in the world of high-stakes real estate, controversy can be a powerful, if blunt, marketing tool.
Conclusion
Narrator: The single most important takeaway from The Art of the Deal is that deal-making, in Trump's world, is not a rigid science governed by spreadsheets and formulas, but a fluid, opportunistic, and deeply personal art. It is a performance that requires a blend of grand ambition, street-smart intuition, relentless persistence, and the masterful manipulation of perception. His success is built on a foundation of challenging conventional wisdom, whether it’s buying a failing hotel, taking on a government project, or trusting a gut feeling over a sure-thing investment.
Ultimately, the book leaves the reader with a challenging question about the nature of success. It presents a blueprint for a style of negotiation that is undeniably effective but also unapologetically aggressive and self-serving. It forces us to ask: In the pursuit of a great deal, where is the line between brilliant strategy and ruthless tactics, and what is one truly willing to do to win?