Trump: The Art of the Deal summary

In the 1970s, Donald Trump was just beginning to make his mark in Manhattan real estate. One of his first big moves was acquiring an option to purchase the Penn Central rail yards. Initially, his plan was to build middle-income housing with government financing. But when the city’s financial problems derailed public funding, Trump didn’t dwell on the setback. 

Instead, he shifted his focus to a new idea: promoting the site as the future home of a convention center. His persistence paid off, and the city ultimately built its convention center on that very site. This ability to adapt and maximize options became a hallmark of Trump’s deal-making strategy.

When Donald Trump first considered the Commodore Hotel, many saw it as a lost cause in a declining part of New York City. Positioned next to Grand Central Station, the hotel was run-down, and the surrounding area was struggling. Where others saw decay, Trump saw opportunity. He noticed the steady stream of affluent commuters passing by daily and believed that with the right vision, the Commodore could be transformed into a thriving success. Trump saw potential for a complete transformation.

He quickly moved to secure an option on the Commodore, allowing him time to put together a deal without risking too much of his own money. His plan involved renovating the old, gloomy building and covering it with a sleek glass façade to give it a modern appearance. To bring this vision to life, Trump partnered with architect Der Scutt and secured the backing of Hyatt Hotels, who were looking to establish a flagship location in New York.

At a time when Donald Trump was still establishing himself as a developer, he set his sights on one of New York City’s prime real estate locations: the Bonwit Teller building at 57th Street and Fifth Avenue. 

It was the early 1970s, and Trump, though young, recognized the potential to transform the site into something iconic. His initial approach to Franklin Jarman, head of Genesco – the company that owned Bonwit – was quickly dismissed. But Trump’s persistence was unwavering. Over the next few years, he continued to follow up, staying on Jarman’s radar until financial troubles forced Genesco to sell assets. This opened the door for Trump to secure the property.

In 1975, a news report about a strike in Las Vegas caught Donald Trump’s attention. Despite Hilton Hotels owning more than 150 properties, just two of their casinos in Las Vegas accounted for 40 percent of their profits. That moment revealed the immense potential of the casino industry to Trump – prompting him to investigate the opportunities in Atlantic City, which was considering legalizing gambling at the time. When the referendum passed in 1976, property values skyrocketed, but Trump waited, choosing patience over speculation.

By 1980, a prime piece of Boardwalk property became available, and Trump saw his chance. The site was strategically located near the convention center, but it came with complications – legal disputes, fragmented ownership, and holdout owners. Where others saw obstacles, Trump saw opportunity. He negotiated long leases and purchased the remaining parcels, ensuring that the entire site was his before moving forward.

Donald Trump scoffed as he read a New York Times article reporting that New York City was restarting the renovation of Wollman Rink after six years of failed efforts and millions of wasted dollars. Frustrated by the city’s inefficiency, Trump compared the ongoing failure to his own successful completion of Trump Tower in the same timeframe. He felt compelled to take action and wrote to Mayor Ed Koch, offering to personally finance and rebuild the rink at no cost to the city.

Koch initially brushed off Trump’s offer, saying the city didn’t need his money and couldn’t accept it even if they wanted to, citing legal hurdles. But this only fueled Trump’s determination. With media support building, the mayor quickly reversed course, granting Trump control of the Wollman Rink project.