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Donald Trump’s decision to repurchase the West Side Yards in 1985 was perhaps his “easiest business decision” (325). Spanning 100 acres of Manhattan riverfront, it was one of the most valuable undeveloped properties in the US. Trump acquired it for approximately $95 million, a fraction of its potential worth, especially compared to other deals, like the $500 million purchase of the Columbus Circle Coliseum site just four blocks away. Trump originally secured an option for the land in 1974, when New York City was near bankruptcy and real estate values were low. However, due to the lack of government subsidies for middle-income housing, community opposition, and financial constraints, he decided not to exercise his option in 1979. The land was then sold to Abe Hirschfeld, who brought in Franco Macri, an Argentinian businessman.
Macri’s inexperience with New York real estate led to a series of mistakes. He made “far too many concessions to the city” (328), agreeing to over $100 million in giveaways, including subway station renovations, a park, and a $40 million Con Edison smokestack. He also failed to generate excitement for his Lincoln West project and designed uninspiring buildings that resembled public housing. Banks refused to finance the project and, by 1984, Macri was facing financial difficulties.
Trump negotiated with Macri and ultimately purchased the property in 1985 with financing from Chase Manhattan. Trump’s vision for the land was completely different. Instead of Lincoln West, he proposed “Television City,” aiming to lure NBC as its anchor tenant. At the time, NBC was considering relocating to New Jersey for tax benefits. Losing NBC would cost New York 4,000 jobs and $500 million annually, as well as the “psychological loss” (335) of such a well-known cultural institution. Trump’s riverfront site offered spacious studio space and the chance for New York City to retain a major network. To generate excitement, Trump announced that Television City would feature “the world’s tallest building” (337)—a 1,670-foot skyscraper taller than Chicago’s Sears Tower. He hired architect Helmut Jahn, known for his daring designs. Trump envisioned 8,000 residential units, TV and film studios, a massive retail promenade, and parks covering nearly 40 acres.
The media immediately latched onto the skyscraper aspect, overshadowing zoning and density concerns. Dan Rather covered it on CBS Evening News, and Newsweek ran a full-page story titled “Donald Trump’s Lofty Ambition” (341). The New York Times questioned whether Trump’s plan represented “great dream [or] vain illusions” (341). Some critics dismissed the 150-story tower as unnecessary, but Trump countered that its boldness would make it a landmark. Columnist George Will praised Trump’s “brashness, zest and élan” (341), arguing that the skyscraper reflected America’s ambition and energy. Trump believed such a bold structure would attract buyers and elevate the entire project’s appeal.
Ultimately, Trump’s strategic patience, negotiation skills, and ability to generate excitement gave him a second chance at an incredibly valuable property. By focusing on NBC, a landmark skyscraper, and public enthusiasm, he revamped the entire project, turning a failed development into a highly anticipated real estate venture. After the initial controversy over the world’s tallest building in Television City, opposition to it began to fade. Instead, critics, particularly Paul Goldberger of The New York Times, focused on how the development integrated with the surrounding neighborhood. Trump disagreed with the criticism, believing that bold, distinctive projects were more successful than those that merely blended in.
By 1986, Television City had stalled in New York City’s bureaucratic approval process. Trump blamed Mayor Ed Koch’s administration, which he described as “pervasively corrupt and totally incompetent” (343). Several high-profile officials in Koch’s administration were indicted for bribery, perjury, or corruption, and city services were failing. Trump believed that many officials avoided making decisions out of fear of legal trouble, leading to bureaucratic paralysis.
The city planning commission pushed for changes to Trump’s design, including more access to the waterfront, better street connectivity, and relocating the skyscraper further south. Although he initially resisted, Trump reluctantly compromised, moving the skyscraper to 63rd Street and agreeing to more pedestrian walkways and parks. He also replaced architect Helmut Jahn with Alex Cooper, a former City Planning Commission member with a good reputation for urban development. Cooper’s design, which included smaller buildings, townhouses, and more public spaces, led to “positive feedback” (348) from critics and city officials.
Meanwhile, Trump was negotiating with NBC, which was considering moving to New Jersey to save up to $2 billion over 20 years. Trump believed that losing NBC would be a disaster for New York, costing thousands of jobs and significant tax revenue. To keep NBC in the city, Trump offered to build NBC’s headquarters at Television City for $300 to $400 million and subsidize their rent at below-market rates. In exchange, he asked for a 20-year tax abatement and offered the city 25% of future profits from the project. Trump’s own advisors opposed the deal, fearing the financial risk of subsidizing NBC for $30 million per year without guaranteed revenue. However, Trump saw the strategic value of securing NBC as an anchor tenant, attracting investors and boosting Television City’s long-term success.
Despite intense negotiations, Koch rejected Trump’s proposal outright, seemingly out of personal animosity. Koch, who may have been embarrassed by Trump’s swift completion of Wollman Rink, refused to cooperate on Television City. Trump publicly criticized Koch’s failure to offer NBC a competitive deal, warning that the city was driving away major corporations like Mobil Oil and J.C. Penney, which had also left New York for lower-cost states. Koch countered by offering NBC a weak, generic tax break that was not competitive with New Jersey’s incentives. Meanwhile, Hartz Mountain Industries, the New Jersey developer, gave NBC a 30-day deadline to accept their deal, further pressuring New York. Despite setbacks, Trump remained confident that Television City would eventually succeed, with or without NBC. He believed Koch’s incompetence would not last forever and that his project’s time would come. He also kept alternative plans open, including residential development or a major shopping complex, ensuring he would profit regardless of the city’s decisions.
In Chapter 1 of The Art of the Deal, Donald Trump lists various deals from a particular week. In the final chapter, he returns to these deals to explain how they played out over time. Some were highly profitable, while others led to strategic retreats.
Trump sold his stake in Holiday Inn at a significant profit before moving to Bally Manufacturing Corporation, where he acquired 9.9% of its stock. Bally resisted his involvement, buying the Golden Nugget casino at a record price to limit Trump’s influence. Ultimately, Bally settled with Trump, buying back his stake for a $20 million profit. He later acquired Resorts International, despite competing bids, gaining control over the Taj Mahal, a massive casino project that had already gone over budget. Trump planned to complete the Taj Mahal and possibly repurpose the older Resorts facility into a “more efficient operation” (357).
Trump and other USFL owners appealed the court ruling that granted them only $1 in damages, despite proving the NFL’s antitrust violations. Meanwhile, Trump’s renovation of Wollman Rink finished $750,000 under budget and a month ahead of schedule. Despite the city’s predicted losses, the rink earned nearly $500,000 in its first year, “all of which went to charity” (358).
Trump partnered with Lee Iacocca to purchase Palm Beach Towers, a struggling condominium project. They turned it around, selling or leasing dozens of units. Trump also planned to open a high-end restaurant in the space. Although he was a finalist for Australia’s second-largest casino, he withdrew his bid, deciding the 24-hour flight from New York made it impractical. Trump bid on the Beverly Hills Hotel but kept his offer low due to concerns about its condition. The property was sold to Marvin Davis, who later attempted to outbid Trump for Resorts International. Trump secured court approval for his deal, and when asked about Davis, Trump mocked his weight, which reportedly infuriated him. Trump is unapologetic because he does not “go out of [his] way to be cordial to enemies” (360).
During construction of Trump Plaza’s new parking garage, a crane accident nearly caused a disaster, but miraculously, no workers were injured. Once completed, the 2,700-space garage significantly boosted revenue at Trump Plaza’s slot machines. Despite exploring Las Vegas casino opportunities, Trump withdrew his application for a gaming license, choosing to focus on Atlantic City. Trump approved production of two Cadillac limousines under his name, the Trump Golden Series and the Trump Executive Series. He declined to create a real estate investment fund, preferring to manage his own capital rather than risk money from investors or friends. Trump received an invitation from Soviet officials to build a hotel in Moscow. He toured potential sites near Red Square and praises “the ambition of the Soviet officials to make a deal” (364). After reading about a Texas company’s executive perks, he bought their luxury 727 jet for $8 million, far below its market value due to the company’s struggles.
Trump concludes by saying he does not know what is next, only that “it won’t be the same” (366). He intends to keep making “deals, big deals” (367) while also finding ways to give back. He values action over intentions, believing that giving time and leadership is more impactful than just donating money.
Chapter 13 is the final chapter in which Trump describes the intricate details of one of his deals. As in the earlier deals, he walks through the difficult process of acquiring the land and makes note of how earlier developments failed in their efforts to build something profitable. However, unlike the Trump Tower project or the Trump Castle casino, Television City is not actually complete at the time of publication. Instead, Trump’s framing switches from present to future tense, layering the text with a sense of forward motion and continued, almost-fated success. His established projects are described in terms of their immediate profitability and lavish displays of luxury, yet the Television City project is presented in conditional terms. Trump speaks about how it will be rather than how it is. This connects directly to Deals as an Art Form, as it showcases Trump’s ability to shape reality through rhetoric—by speaking about the deal in a way that makes it feel inevitable, he reinforces the idea that business success is about perception as much as execution.
In this way, the Television City chapter—particularly the closing paragraphs of the Television City chapter—gives the audience an insight into the sales technique Trump uses during the construction of his building projects. He is selling the audience on his vision, just as he sells investors and critics. Just as the opening chapter allowed the audience to gain a glimpse into the day-to-day life of Donald Trump, Chapter 13 allows the audience to experience what it is like to be an investor in a Trump project. The ambitious rhetoric and the grand plans are not yet ready for the public, but Trump is offering an exclusive glimpse into the future. This also ties into the theme of No Publicity Is Bad Publicity, as Trump understands that even an unfinished project—if positioned correctly—can generate excitement and momentum that will eventually translate into financial gain. In this sense, the text itself can be considered a marketing tool for Television City, as closing with this project means that it is the final takeaway for the reader. Structurally, this narrative choice is highly strategic and aligns with the major principles of successful people that Trump revisits throughout the text.
In Chapter 14, the structure of the book changes once again. The final chapter looks back to the opening chapter, giving the audience an insight into how the various deals and projects described in Trump’s typical week played out. Rather than giving too much detail, however, Trump treats this section almost as a way to settle scores. Many of the projects are dismissed in a few sentences with the promise of great profits to come, while other entries spend entire paragraphs settling social disputes.
Trump’s comments about Marvin Davis, for example, are probably the most personally insulting in the entire book, even though Davis is not a prominent figure in any chapter. Ed Koch, in contrast, does not make a return in the final chapter even though he has borne the brunt of Trump’s ire for much of the text. Rather, the final chapter is an opportunity for Trump to settle old scores with old enemies. This choice ensures that the reader walks away with a clear sense of Trump’s dominance over both business rivals and personal antagonists. Even when he describes negative interactions, they serve as reminders of his influence and strategic thinking. These disagreements are just deals in another guise, with Trump using his public platform to forward his position.
The closing chapters of the book also look to the future. Just as Trump talks about Television City in the future tense, he ponders positively on the possibility of his future deals. The construction of a hotel in Moscow, for example, is an exciting opportunity for Trump. As the living, breathing embodiment of a certain kind of 1980s hyper capitalism, Trump’s interest in building a hotel in the heart of Soviet Russia is an ironic collision of ideologies. The Soviet Union, built on state-controlled industry and communist economics, represented the opposite of the free-market capitalism and wealth-driven ambition that Trump championed. Whether he acknowledges it or not, his venture into Moscow underscores the waning power of Soviet communism and the creeping influence of Western capitalism.
Similarly, the acquisition of a private jet is another example of Trump associating his name not only with luxury but also with great deals. The plane is not just a flying advertisement for Trump’s lavish lifestyle; he also wants the world to know that he got it at a great price, a more important factor for Trump who is yet to even fly aboard his own plane. Trump’s emphasis on the deal itself, rather than just the purchase, reflects his belief that smart negotiations define success more than mere ownership. In his worldview, wealth is not just about accumulation but about the ability to outmaneuver competitors and secure the best terms. This moment reinforces how Trump consistently turns material acquisitions into brand-enhancing moments, ensuring that every financial move also serves a larger public relations purpose.
The Art of the Deal was published in 1987. In many ways, the closing chapter—brimming with opportunism and braggadocious ambition—represents the high-tide point in Trump’s career as a real estate developer. The closing chapter signposts his hope for the future, which—when contrasted with the struggles which affected him in the following years—add a touch of nuance to Trump’s relentless portrayal of luxurious success. Ultimately, the book ends as it began: with Trump positioning himself as a visionary who is always looking ahead to the next deal. This reinforces the theme of Business, Memoir, and the Making of a Persona, as Trump ensures that his legacy, as presented in the book, is one of perpetual forward momentum, regardless of the obstacles or contradictions that may arise.



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