65 pages • 2-hour read
Trump: The Art of the Deal
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Chapters 10-12Chapter Summaries & Analyses
Chapter 10 Summary: “Low Rent, High Stakes: The Showdown on Central Park South”
At 100 Central Park South, Donald Trump’s attempt to demolish two buildings and build a luxury condominium faced intense resistance from tenants. Although the tenants succeeded in delaying him, real estate values soared during the legal battle, ultimately making his project more profitable than originally planned.
In 1981, Trump purchased 100 Central Park South, a rent-controlled residential building, and the Barbizon-Plaza Hotel next to it, securing “one of the best pieces of real estate anywhere in the world” (250) at a favorable price. The buildings were not generating much profit, but Trump saw immense real estate potential. His plan was to vacate both buildings, demolish them, and build a luxury tower. However, he underestimated how fiercely tenants would fight to keep their below-market-rate apartments in a high-end location. Rent control laws made evicting tenants “almost impossible” (252). Wealthy tenants had the most to lose and organized a legal battle, hiring top attorneys and contributing thousands of dollars to block Trump’s project. Trump later researched the tenants’ finances and found that many were affluent professionals or celebrities, including fashion designers, attorneys, and stockbrokers, enjoying massive rent subsidies. Even Ed Koch, the Mayor of New York and longtime Trump antagonist, had a rent-controlled apartment. He argued that rent-control laws were outdated, benefiting the rich instead of those in need.
Instead of personally negotiating, Trump hired Citadel Management to relocate tenants. However, the tenants formed a committee, resisted relocation offers, and framed Trump’s efforts as harassment. While Trump provided all essential services, minor cost-cutting measures—like removing doormen’s uniforms and replacing hallway lights with energy-efficient bulbs—were twisted into evidence of harassment. The tenants’ attorneys exploited these tactics, tying up the eviction process in legal disputes. Trump also attempted a bold PR move, offering vacant apartments to the homeless to pressure tenants into leaving. However, the media criticized his motives, and city officials declined the offer. Trump later backed out after realizing that once occupied, evicting anyone would be legally impossible. He uses this as evidence for his advice: “don’t act on impulse—even a charitable one—unless you’ve considered the downside” (264).
Legal battles continued for years. In 1984, tenants officially filed harassment charges with the state, despite, Trump claims, lacking evidence. Many complaints were minor or fabricated, Trump says, but the politically charged dispute put Trump on the defensive. Wealthier tenants orchestrated a media campaign, labeling Trump a “modern-day Scrooge” (264), even though some had been using similar legal tactics for decades to reduce their rent. Despite these setbacks, Trump remained resilient. He refused to be blackmailed into a settlement, preferring to fight the legal battles. Ultimately, although the original demolition plan failed, Trump adapted and developed a more profitable project than initially planned.
The lesson Trump took from the experience was that tenants, especially wealthy ones, will fight fiercely to protect a great deal. More importantly, he learned not to act impulsively, whether with tenant negotiations or charitable gestures like the homeless housing offer, without considering potential legal and PR consequences. In the end, persistence and market timing worked in his favor, turning what seemed like a loss into a victory. Donald Trump’s legal battle over 100 Central Park South initially seemed like a loss, but delays caused by tenants ultimately boosted his profits. Real estate values soared during the prolonged fight, making his project far more lucrative than originally planned.
Zoning laws also forced a design change. If he demolished the Barbizon, the new building had to be smaller. Instead, Trump opted for renovation, enlarging windows and modernizing the interior while preserving its classic exterior. This decision saved $150 million compared to constructing a new tower and aligned with shifting architectural trends favoring historical elegance over sleek modern designs. At the same time, Trump acquired the St. Moritz Hotel, across the street from the Barbizon, from legendary real estate figures Harry Helmsley and Lawrence Wien. By closing the Barbizon, he moved its best staff and guests to the St. Moritz, increasing its occupancy and profitability. Banks backed this deal, giving Trump $6 million more than his purchase price, meaning he bought it with zero investment.
The harassment lawsuit dragged on, but when Trump abandoned demolition plans, most tenants dropped their claims. Eventually, an appellate court ruled in his favor. With legal obstacles cleared, Trump rebranded the Barbizon as Trump Parc and launched sales before renovation was even completed. Within eight months, 80% of the units sold, generating over $240 million in revenue. In the end, Trump made over $100 million, tenants kept their apartments, and the city gained higher tax revenues. Ironically, the delays he fought against ultimately worked in his favor, turning a seemingly “total loser” (272) of a project into one of his most profitable real estate deals.
Chapter 11 Summary: “Long Shot: The Spring and Fall of the USFL”
Donald Trump purchased the New Jersey Generals football team in 1983, seeing it as a fun challenge with high-risk, high-reward potential. The United States Football League (USFL) was struggling against the dominant NFL, but Trump believed it could succeed with the right strategy, including moving its season from spring to fall and signing top players. Trump quickly pushed for a fall season, arguing that football fans and TV networks were only willing to pay big money for fall games. The NFL’s television contracts were worth $359 million annually, while the USFL received only $1 million from ABC for spring games. Trump believed moving to fall would either force a lucrative TV deal or provide grounds for an antitrust lawsuit against the NFL.
Trump also studied previous leagues that competed with the NFL. The American Football League (AFL) spent heavily, signed top players, and eventually merged with the NFL, while the World Football League (WFL) lacked funding and vision, leading to bankruptcy in two years.
Trump invested heavily in the Generals, bringing in NFL-level talent to build excitement. His biggest signing was quarterback Brian Sipe from the Cleveland Browns, to whom he offered $800,000 per year. He also lured Gary Barbaro, Kerry Justin, Willie Harper, Bobby Leopold, and Dave Lapham. He even attempted to recruit Don Shula, legendary coach of the Miami Dolphins, but refused Shula’s demand for a Trump Tower apartment.
Trump’s boldest move was signing Lawrence Taylor, the NFL’s top linebacker, to a futures contract. The New York Giants panicked, offering Taylor $6.55 million to stay, and Trump agreed to release him for a $750,000 penalty fee, a huge win for the USFL’s credibility. Encouraged by Trump’s “aggressiveness” (280), other USFL teams signed top college players, including Heisman Trophy winners Mike Rozier and Steve Young. However, the league still struggled, with weak teams in Chicago, San Antonio, and Oklahoma dragging down its image.
At a 1984 league meeting, Trump forced a vote on moving to the fall, winning a two-thirds majority. This antagonized the NFL, which secretly strategized to crush the USFL. Leaked documents revealed a plan to pressure TV networks not to sign USFL deals. Seeing no TV contract, the USFL sued the NFL for $1.32 billion, accusing it of monopoly tactics.
With the USFL’s financial situation worsening, Trump made one last high-profile signing: Doug Flutie, the Heisman-winning quarterback from Boston College, offering him $1 million per year. His first game drew massive TV ratings, proving his marketing value. The Generals thrived, Trump says, with Herschel Walker breaking the all-time professional rushing record (2,411 yards). However, Flutie’s late-season injury cost them a chance at the championship.
Trump’s strategy of moving to fall and suing the NFL put the USFL on the brink of success or total collapse. The league’s future depended on winning in court or forcing the NFL to settle.
In February 1986, the USFL reduced its teams from 14 to 8, consolidating its strongest franchises. The New Jersey Generals merged with the Houston Gamblers, creating an elite backfield with Herschel Walker and Jim Kelly. The league’s future depended on its antitrust lawsuit against the NFL, which was set for trial in May 1986.
During the trial, USFL lawyer Harvey Myerson aggressively attacked NFL Commissioner Pete Rozelle, exposing his contradictions and making him seem “flustered” (291). Myerson presented evidence showing the NFL pressured networks to block a fall TV contract for the USFL. He also revealed a secret Harvard seminar where the NFL strategized to destroy the USFL. The trial seemed to favor the USFL, with Sports Illustrated reporting that it had won the “first round” (294). However, the jury’s sympathy shifted toward the NFL, as Rozelle’s weak testimony and NFL attorney Frank Rothman’s illness “elicited further sympathy” (295) from the jury. Trump also believed he was unfairly portrayed as a ruthless billionaire, while the NFL positioned itself as the underdog.
In July 1986, the jury ruled that the NFL had violated antitrust laws but awarded the USFL just $1 in damages, effectively killing the league. Many jurors later admitted they misunderstood the legal process, with some believing the judge would adjust the damages. With no TV contract and massive losses, the USFL suspended operations. Many of its best players, including Walker and Kelly, transitioned to the NFL. Though disappointed, Trump saw the USFL as a learning experience. He remained open to future football ventures, even considering joining a new fall league. However, the USFL’s collapse secured the NFL’s monopoly, preventing competition in professional football. As a result, Trump believes that “the biggest losers” (297) are the football fans, though he managed to treat the venture as an expensive opportunity to learn.
Chapter 12 Summary: “Ice Capades: Rebuilding Wollman Rink”
In 1986, Donald Trump took over the long-delayed renovation of Wollman Skating Rink in Central Park after the city had failed for six years and lost $13 million. Upon reading a New York Times article stating that the city planned to start over and take two more years, Trump offered to complete the rink himself in four months. Initially, his offer was rejected by Parks Commissioner Henry Stern, and Mayor Ed Koch “belittled” (304) it. However, once Trump’s offer became public, media backlash forced the city to reconsider. With public pressure mounting, officials agreed to let Trump handle the project, funding it himself and being reimbursed upon completion.
Trump quickly discovered major mismanagement. The city’s Freon-based cooling system was flawed, and the rink had been built on an uneven slope, making ice formation impossible. He hired Canadian experts from Cimco, a top ice-rink builder, who advised using a brine-based system, a proven and durable alternative. Instead of tearing out the botched foundation, Trump decided to build on top of it, saving time and costs. With strong leadership, Trump visited the site daily, ensuring efficiency and accountability. The project moved at record speed. Trump noted that the press played a key role in forcing the city’s hand, as public pressure is the only real motivator for politicians. He also criticized the city’s bureaucratic inefficiency, where no one was held accountable for the disastrous mismanagement.
One symbolic incident epitomized city incompetence: a crew of six workers attempted to plant a tree in Trump’s honor but destroyed freshly planted sod by driving over it. This, Trump said, was “a perfect metaphor” (315) for the city’s dysfunction. The Wollman Rink became a success story, proving that “effective private enterprise” (317) could outperform government bureaucracy. Trump later operated the rink, ensuring it remained profitable and well-maintained. His experience reinforced his belief in strong leadership and efficiency in business and politics. After completing the Wollman Rink renovation, Trump received a “gracious” (320) letter from former Parks Commissioner Gordon Davis, who acknowledged his past mistakes and praised Trump’s success. In contrast, Henry Stern and Mayor Ed Koch downplayed Trump’s accomplishment. The media harshly criticized the city’s six-year failure, which likely made Koch defensive.
Despite publicly promising to learn from the Wollman Rink success, Trumps says, city officials never followed up to apply its lessons to other projects. Trump believed the city’s failures stemmed from “incompetence” (321) and lack of leadership rather than legal constraints like lowest-bid contract laws and the Wicks law, which divided projects among multiple contractors. He suggested objective standards for selecting qualified contractors and rewarding good performance. The real issue, Trump argued, was accountability. Contractors overcharged the city, and officials lacked the knowledge or willpower to challenge them. The Wollman Rink debacle illustrated this. One official, Bronson Binger, promised to resign if the rink was not completed but was later promoted to oversee prison construction. Trump lamented the decision to “reward failure” (323).
The rink’s grand opening featured world-class skaters and, to avoid delays, Trump was asked to operate it temporarily. He chose Ice Capades to manage the rink, ensuring quality and profitability. In its first year, revenue jumped from $100,000 to $1.2 million, with $500,000 in profits going to charity. Trump took pride in revitalizing the rink, watching skaters from Trump Tower, though he noted he avoids skating himself, as too many people wanted to “watch [him] fall” (324).
Chapters 10-12 Analysis
The Art of the Deal describes many of Donald Trump’s greatest successes throughout the 1980s, but this section discusses failures that are carefully framed by Trump as a coauthor. This pattern also reinforces the theme of Business, Memoir, and the Making of a Persona, as Trump carefully curates the narrative of his career, ensuring that even setbacks are framed as learning experiences or stepping stones to greater success. In previous chapters, Trump presented himself on an almost-constantly upward trajectory. In Chapter 10 and Chapter 11, however, he delves into two of his highest profile failures. The struggles to redevelop a rent-controlled apartment block and the difficulty of setting up a rival football league each merit a chapter in which Trump delves into why he failed. Yet even in these chapters—which seem designed to soften Trump’s brazen attitude and introduce a chastening element of humility to his persona—Trump flips failures into successes, whether by highlighting a lesson learned, a failure laying the groundwork for a later success, or by presenting the failures of others’ as a contrast.
In the case of the rent-controlled apartment block, Trump introduces a secondary narrative halfway through the chapter which enjoins the struggles against the tenants with a nearby property that he is also redeveloping. While he loses against the tenants, this second project emerges as very profitable, allowing Trump to present his big failure alongside a success story. This reframing ties into the theme of No Publicity Is Bad Publicity, as Trump ensures that even controversial or negative situations ultimately contribute to his image as a dealmaker who always finds a way to win, even if the success, as in this case, is a matter of happenstance rather than intentional planning. This refusal to allow failure to be presented alone is a rhetorical strategy that defines failure in the text to mean delayed success.
The failure of the USFL is different. Unlike his other projects, Trump is not the sole lead on the USFL project. This is not a real estate deal or a property development; he is one among many other team owners, many of whom are also wealthy and successful. When the league fails to win its case against the NFL, the USFL is a failing proposition. Yet Trump is not willing to concede defeat. The court’s ruling was in his favor, he claims, even though the amount awarded was a token gesture and far lower than what the USFL sought. Trump blames the other owners for the failure: They failed to adhere to the doctrines of Trump, so their failure became inevitable. This shift in blame aligns with the theme of Deals as an Art Form, as Trump portrays himself as possessing a unique, instinctive business acumen that others lack. By presenting himself as the only person who could have made the USFL successful, he implicitly reinforces the idea that dealmaking is a rare skill that sets him apart from the rest. In effect, this stark failure becomes a pronounced validation of The Art of the Deal itself, suggesting that Donald Trump cannot fail, he can only be failed. If the other owners had abided by Trump’s business strategies, then the USFL, Trump suggests, may have been a success.
After two chapters dedicated to apparent failures, Chapter 12 reverts back to the stories of success. The account of Trump’s involvement in the Wollmann ice rink is markedly different to the earlier stories, however. The building of Trump Tower, the construction of luxury apartment blocks, and the growing involvement in the casino industry are designed to personally enrich Donald Trump and enhance the Trump brand. The rebuilding of the ice rink, however, is different because it purports to be in the interest of the public above all else. Trump insists that he does not stand to commercially benefit from the project, offering to give any profits to charity. Instead, he frames his involvement in terms of disgust with the government’s inefficiency. This chapter plays directly into No Publicity Is Bad Publicity, as it functions as a public relations success story, allowing Trump to present himself as a civic-minded businessman who steps in where the government fails. As the ultimate dealmaker, he is personally appalled at the government’s failure to get a deal done. As a real estate developer, he is professionally disgusted by the way in which the project is being run. As a New Yorker, he insists, his pride in his city is hurt every time he walks by the unfinished ice rink. His ability to frame his intervention as both a business decision and a civic duty demonstrates the advantage of a hybrid memoir form, as he transforms what could have been an ordinary construction project into a masterful display of business acumen, leadership, and strategic publicity.
The Wollman ice rink is a small-scale project for Donald Trump, but perhaps it is the most personally satisfying deal in the book. Not only does it allow him to show the audience how his talents can be used for the public good as well as personal enrichment, it allows him to frame himself as a high-level humanitarian. This moment reinforces Business, Memoir, and the Making of a Persona, as Trump positions himself as both a businessman and a problem-solver whose instincts are superior to government bureaucracy. After his failure with the USFL and his castigation in the press while trying to evict tenants from rent-controlled apartments, the Wollmann ice rink is more than just a small project: Trump is not just rebuilding the ice rink; he is rebuilding his public image.
As well as rebuilding his public image, the ice rink project allows Trump to delve into his more ideological rhetoric. Throughout the book, Ed Koch is presented as the embodiment of government overreach, inefficiency, and corruption. The Mayor of New York represents everything that Donald Trump dislikes, so that he credits the mayor with personally intervening to curb his ambition, thus hurting the city in many ways. This moment underscores Trump’s marketing approach, as Trump ensures that his public feud with Koch remains a central narrative in the book, reinforcing his outsider status and positioning himself as the more competent figure in contrast to government officials. Ed Koch is denying the people of New York the opportunity to enjoy Trump’s beautiful buildings and recreation activities that only he can deliver, the book suggests.
In the Wollman ice rink, Trump lists anecdotes from the site, showing the audience the ways in which the project was run inefficiently. Each anecdote adds weight to Trump’s rhetoric, especially when contrasted against his almost immediate success. As well as rebuilding the ice rink and rebuilding his image, the Wollmann project is a big success for Donald Trump because it validates his belief in the supremacy of private enterprise over government inefficiency. The project is central to the text because it merges a successful deal with the failure of government and the power of public support—three key ideas that Trump reiterates across the text.
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