1장
The Dealmaker's Dark Side: Trump's Rise to Power
Donald Trump's 2015 presidential candidacy announcement wasn't the vanity project most journalists dismissed it as. Having followed Trump intensely since 1988, investigative reporter David Cay Johnston recognized a modern P.T. Barnum selling his own version of Barnum's famous fakes. Trump had been eyeing the presidency since 1985, previously proposing himself as Bush's running mate in 1988, briefly running with the Reform Party in 2000, and testing waters again in 2012. His 2016 run coincided with declining TV ratings that threatened his show's cancellation. What mainstream media missed was Trump's genius at exploiting journalistic conventions while concealing entanglements with cocaine traffickers, mobsters, and con artists. Even those applauding crowds at his announcement? Many were actors paid fifty dollars apiece. Johnston's decades of documentation reveal a man who masterfully deflects investigations, threatens litigation against news organizations, and bluffs rather than admitting ignorance-tactics that would define his political career just as they shaped his business empire.
2장
The Trump Legacy: From Drumpf to Donald
The Trump family's German roots trace back to the war-torn seventeenth century when they were known as Drumpf before simplifying their name in 1648. Their chosen surname would prove prophetic-while "trump" can mean a winning play that outranks others, it also carries definitions like "a thing of small value," "to deceive or cheat," and "to devise in an unscrupulous way."
Donald's grandfather Friedrich Trump established the family's entrepreneurial pattern when he fled Germany at sixteen to avoid military service. In America, he opened The Dairy Restaurant in Seattle with a likely curtained-off whorehouse. During the Klondike gold rush, he "mined the miners" with The Arctic, a bar offering hard liquor and prostitutes. After making his fortune, Friedrich returned to Germany, married Elizabeth Christ, but was ultimately expelled for his earlier draft dodging. Back in New York, he prospered until dying in the 1918 influenza pandemic.
Fred Trump, only twelve when his father died, quickly followed in his entrepreneurial footsteps, starting a garage-building company with his mother at fourteen. His early history included a 1927 arrest during a Ku Klux Klan riot in Queens-an incident Donald would later deny despite clear documentation. After building single-family homes in Queens and running a successful self-service grocery during the Depression, Fred secured lucrative government contracts during and after World War II, becoming notorious for using cheap materials in his 27,000+ subsidized apartments while mastering government financing programs.
When Donald was still in diapers, he and his siblings had trust funds worth about $12,000 annually-roughly four times the typical family income in the late 1940s. Fred ran his business from an austere Brooklyn office, where contractors would present plain envelopes containing cash before discussing contract terms-a common but illegal practice that padded costs passed to the government or tenants.
Donald, described as "maladjusted" in his youth, was sent to military school as a teenager after numerous behavioral problems. He avoided Vietnam through four student deferments and a medical exemption for a bone spur. After graduating from the University of Pennsylvania with an economics degree, Donald began modeling himself after his father, even driving a Cadillac with personalized plates like his father did.
3장
The Trump Doctrine: Revenge and Paranoia
In 2005, Donald Trump delivered a motivational speech in Loveland, Colorado that revealed his core philosophy. Unlike typical inspirational speakers, Trump's unscripted, profanity-laden rant attacked former wives, business associates, and even the Denver airport. His core advice boiled down to two principles: trust no one, especially good employees ("Be paranoid"), and embrace revenge as business policy ("Get even").
Trump expanded on his revenge philosophy in his 2012 book "Think Big," devoting an entire chapter to the subject. "I always get even," he writes, detailing how he destroyed a former employee's career after she refused to make an improper call to a banking friend during his financial troubles. He proudly describes going "out of his way to make her life miserable" and giving her bad recommendations.
This revenge doctrine directly contradicts the biblical teachings Trump claims to revere. While he told a radio host he values "an eye for an eye" from Exodus, he seems unaware that Jesus explicitly rejected this principle in the Sermon on the Mount, instructing followers to "turn the other cheek" and "love your enemies."
Trump's motto-"Always get even. When someone screws you, get them back in spades"-was dramatically demonstrated after his father died in 1999. At Fred Sr.'s funeral, Fred Trump III spoke warmly of his grandfather. Days later, Fred III's newborn son William began having seizures, requiring extensive medical care costing nearly $300,000. Initially, the Trump family business promised to cover all medical expenses.
However, when Fred III and his sister Mary discovered they'd been largely cut out of Fred Sr.'s will (receiving only $200,000 compared to the millions going to Donald and his three surviving siblings), they filed a lawsuit claiming Fred Sr. wasn't of sound mind when signing his 1991 will. Donald's revenge was swift-he terminated all medical benefits for William, potentially endangering the child's life. When questioned about this seemingly heartless act, Donald remained unapologetic: "Why should we give him medical coverage?" and "It's cold when someone sues my father."
4장
The Roy Cohn Connection: Trump's Mentor
In 1970, Donald Trump was still an outer-borough Queens resident yearning to join Manhattan's elite. One of his most significant early connections was with Roy Cohn, the notorious attorney who had served as chief lawyer for Senator Joseph McCarthy's communist witch hunts. Trump described Cohn as becoming "a business mentor and nearly a second father," someone who could be "vicious" and "would brutalize for you."
Their relationship deepened when Trump hired Cohn to fight a federal housing discrimination lawsuit in 1973. The government had conducted tests showing Trump properties were steering minority applicants to certain buildings while telling white applicants about vacancies in others. While most landlords quickly settled such cases, Cohn advised Trump: "Tell them to go to hell and fight the thing in court." Trump followed this advice, holding a press conference where he mischaracterized the racial discrimination case as being about welfare recipients, while Cohn filed a $100 million countersuit against the government.
This wasn't the first such allegation against the Trumps. Two decades earlier, folk singer Woody Guthrie had written pointed lyrics about Fred Trump's rental policies at Beach Haven, his 1,800-unit apartment project where Guthrie lived in 1950. In a song titled "Old Man Trump," Guthrie condemned the "color line" Fred had drawn, writing "Beach Haven is Trump's Tower/Where no black folks come to roam."
When the government tested Trump properties in 1972 under the Fair Housing Act, they found clear evidence of discrimination-at Shore Haven apartments, a superintendent told a white woman she could choose between two units shortly after telling a black woman there were no vacancies. Court records showed minority applicants were routinely steered to buildings that already had high minority occupancy.
Despite Cohn's aggressive tactics, Trump ultimately lost when Judge Edward Neaher dismissed his countersuit and allowed the government's case to proceed. Trump folded and settled, agreeing to run advertisements soliciting non-white tenants and end discriminatory practices including secret coding of applications. Yet he spun this complete loss as a victory, claiming "the government couldn't prove its case."
5장
The Concrete Kingdom: Trump and the Mob
In 1981, Trump negotiated perhaps his most lucrative deal ever-convincing New Jersey Attorney General John Degnan to limit the investigation into his background for a casino owner's license. Despite regulations requiring exhaustive personal history disclosures and investigations typically lasting 18 months, Trump secured a promise to complete the process in just six months by threatening to build in New York instead.
Trump failed to disclose four previous government investigations on his application, including a federal grand jury inquiry into his Penn Central railroad yards deal, an investigation into his Commodore Hotel acquisition, FBI questioning about his dealings with mob associate John Cody, and the 1973 racial discrimination lawsuit. The Division of Gaming Enforcement gave Trump a pass on these omissions, noting in a footnote that he had "volunteered" the information just before their report was completed.
Beginning in 1978, Trump chose to build Trump Tower with ready-mix concrete rather than steel girders, despite other developers pleading with the FBI to free them from a mob-run concrete cartel that inflated prices. This made Trump vulnerable to union work stoppages, as the teamsters controlled concrete delivery, construction unions controlled site access, and concrete workers controlled pouring-all ultimately controlled by the mob.
Trump bought his concrete from S & A Concrete, secretly owned by Mafia chieftains Anthony "Fat Tony" Salerno and Paul Castellano. With Roy Cohn as his fixer, Trump had protection-Salerno and Castellano were Cohn's clients. When cement workers struck in summer 1982, concrete continued flowing at Trump Tower. Witnesses reported seeing Trump meeting with Salerno at Cohn's townhouse, though Trump later denied this under oath.
Federal prosecutors eventually brought a major case against eight mobsters, including Salerno, for inflating concrete prices for Trump's East 61st Street apartment building. In 1986, they were convicted in a racketeering trial that the prosecutor called "the largest and most vicious criminal business in the history of the United States."
6장
The USFL Gamble: Trump's Football Folly
Football, not buildings, brought Trump the national fame he craved. In 1983, he purchased the New Jersey Generals of the fledgling United States Football League for between $5-9 million. While USFL founder David Dixon had envisioned a patient, low-cost spring league that would gradually build to compete with the NFL, Trump had grander ambitions.
The USFL initially showed promise with decent attendance averaging 25,000 per game, television contracts with ABC and ESPN, and fan-friendly innovations like touchdown celebrations and instant replays. But Trump quickly abandoned Dixon's cautious strategy for showmanship and high-stakes gambling that would ultimately destroy the league.
Trump staged media spectacles like cheerleader tryouts judged by celebrities in Trump Tower, sent the "Brig-A-Dears" to bars without security (prompting a walkout), and violated salary caps to sign stars like Heisman Trophy winner Doug Flutie. Most fatally, in 1984 he convinced other USFL owners to sue the NFL for antitrust violations, hiring his mentor Roy Cohn rather than an antitrust specialist.
For the trial, Trump hired Harvey Myerson, a colorful litigator with no antitrust expertise. After a 48-day trial, the jury found the NFL guilty of monopolistic behavior but awarded just $1 in damages (automatically tripled to $3 under law). The USFL promptly folded. The appeals court explicitly rejected Trump's strategy, noting that "new sports leagues must be prepared to make the investment of time, effort and money" rather than seeking "entry into the NFL on the cheap."
Years later, Trump appeared in an ESPN documentary about the USFL's demise, walking out when questioned about his strategy. He later sent the filmmaker a note calling him "a loser"-demonstrating his pattern of dismissing those who don't support his self-image.
7장
The Weichselbaum Mystery: Trump's Inexplicable Loyalty
Among Trump's most mysterious criminal associations was with Joseph Weichselbaum, a three-time felon and major cocaine and marijuana trafficker who operated a helicopter service for Atlantic City casinos. Trump repeatedly risked his valuable casino license to help Weichselbaum for reasons that remain inexplicable, given that associating with known felons could have resulted in the revocation of his gaming permits worth hundreds of millions of dollars.
Despite Weichselbaum's company, Dillinger Charter Services, going bankrupt multiple times and having a questionable safety record, Trump continued paying over $2 million annually for helicopter services when better-financed and more reputable competitors were readily available. The relationship extended beyond business - Trump personally owned apartment 32-C at Trump Plaza condominiums which he rented to the Weichselbaum brothers under unusual terms-$3,000 monthly in cash paid directly to Trump, with the remainder compensated through helicopter services. This arrangement raised red flags among investigators due to its deviation from standard business practices and the cash-only component.
When Weichselbaum faced sentencing for drug trafficking charges in 1985, Trump took the extraordinary step of writing a personal letter to Judge Harold Ackerman (who replaced Trump's sister, Judge Maryanne Trump Barry, after she recused herself) describing the drug trafficker as "a credit to the community" and "conscientious, forthright and diligent." This intervention was particularly notable given Weichselbaum's extensive criminal history, including previous convictions for grand theft auto and embezzlement. While other defendants in the same case received sentences up to twenty years, Weichselbaum served only eighteen months, raising questions about potential influence.
After his release from prison, Weichselbaum moved into Trump Tower apartments worth $2.4 million, despite having declared bankruptcy. He later claimed intimate knowledge of Trump's personal affairs, including details about Trump's relationship with Marla Maples, even suggesting Trump had asked him to accommodate Maples at his apartment. These claims added another layer of intrigue to their already complex relationship.
The extent of their connection became a political issue during the 2016 presidential campaign when Trump claimed he "hardly knew" Weichselbaum. This assertion contradicted extensive documentation, including Trump's character witness letter, the unusual rental arrangements, the continued business relationship despite Weichselbaum's criminal history, and multiple witnesses who attested to their regular social interactions throughout the 1980s and early 1990s.
8장
The Financial Facade: Trump's Elastic Net Worth
Over four decades, Donald Trump has declared wildly varying figures for his net worth, sometimes differing by billions within days. In 1990, when his empire verged on collapse, Trump claimed $3-5 billion while bank reports showed him $300 million in debt.
When sued for defamation by journalist Tim O'Brien who estimated Trump's worth at $150-250 million (not billions), Trump gave remarkable testimony about how he calculates his wealth: "My net worth fluctuates, and it goes up and down with markets and with attitudes and with feelings, even my own feelings." Trump explained that his self-valuation changes based on his emotional state and "general attitude at the time."
The court dismissed Trump's lawsuit, noting his financial statements contained significant departures from generally accepted accounting principles. His accountant Gerald Rosenblum testified he simply accepted Trump's list of liabilities without verification: "I'm not certain to this day that I was aware of all Mr. Trump's liabilities."
Trump routinely overstates asset values while understating or hiding debts. For example, he claimed to have paid cash for Mar-a-Lago, but later testimony revealed Chase Manhattan had loaned him the entire $8 million purchase price via an unrecorded mortgage. Trump contributed just $2,800 cash while receiving $10 million total from the bank on his personal guarantee.
Between 1986 and 1990, Donald Trump took in at least $375.2 million from his business enterprises-averaging $1.6 million weekly or $2.66 per second. Yet by spring 1990, he couldn't pay his bills. Despite claiming to be worth $3 billion, Trump couldn't make a $73 million mortgage payment on Trump's Castle Casino or pay contractors for his newly opened Trump Taj Mahal.
The Kenneth Leventhal accounting firm, hired by Trump's 70 creditor banks, determined his actual net worth was negative $295 million. With Trump facing imminent collapse, the Casino Control Commission effectively deemed him "too big to fail" by threatening to withhold casino licenses from banks if they foreclosed. This government intervention saved Trump from bankruptcy, allowing him to pay back less than he owed while receiving $60 million in new loans.
9장
Trump University: Education or Exploitation?
In 2004, Michael Sexton pitched Donald Trump on licensing his name for online real estate courses. Trump instead decided to own the company outright, giving Sexton a 5% stake and $250,000 salary to run it. In promotional videos, Trump claimed "At Trump University, we teach success" and promised "professors and adjunct professors that are absolutely terrific" who would be "handpicked by me."
These claims were false. The operation wasn't a university in either the common understanding or under New York law, which prohibits unauthorized use of the term "university" in business names. Despite being ordered to stop using the name "university," Trump ignored these demands for five years. The "faculty" weren't professors but commissioned salespeople, many with no real estate experience. When deposed in 2012, Trump couldn't identify a single instructor, contradicting his claim of handpicking them.
In Texas, undercover state consumer fraud investigators found Trump University taught outdated information "of little practical value" and used high-pressure sales tactics to push students into purchasing the $35,000 "Gold Elite" package. Students were instructed to call credit card companies during sessions to increase their credit limits. Despite investigators recommending a $5.4 million restitution demand and permanent ban from Texas, Attorney General Greg Abbott took no public action. Three years later, Trump donated $35,000 to Abbott's gubernatorial campaign.
Similarly in Florida, Attorney General Pam Bondi announced considering joining New York's fraud investigation against Trump University, but dropped it after receiving a $25,000 check from the Trump Foundation to her campaign. This donation violated federal law prohibiting charities from making political contributions. When questioned, Trump's foundation claimed the donation was mistakenly reported as going to a Kansas charity with a similar name.
10장
The Master of Deception: Trump's Alter Egos and Marketing Tactics
After destroying the Bonwit Teller building's art facade, Trump avoided direct criticism by inventing "John Baron, a vice president of the Trump Organization" who spoke to The New York Times explaining why preserving the sculptures would have been too costly and dangerous. For years, Trump called journalists posing as John Baron (or Barron), planting stories about women being in awe of him or upcoming business deals.
In June 1991, NBC's Today Show reported that Trump had ended his relationship with longtime girlfriend Marla Maples and begun dating Italian model Carla Bruni. When People magazine reporter Sue Carswell called for an interview, she received a call back from "John Miller," a supposed new publicist who detailed Trump's relationships with beautiful women. Carswell immediately recognized that Miller was actually Trump himself. When confronted, Trump initially admitted the deception to Carswell, but years later on Howard Stern's show, he continued to imply he had dated Bruni, even after she became France's First Lady. Bruni later told the Daily Mail, "Trump is obviously a lunatic. It's so untrue and I'm deeply embarrassed by it all."
Trump relies on two core strategies to manage his public image: exploiting news reporting weaknesses through legal threats, and distorting information while blocking inquiries into his conduct. When confronted with the "John Miller" tape on the Today Show, Trump flatly denied it despite previous admissions. His strategy turns hard facts into uncertainty, as demonstrated when CBS News framed the clear evidence as "mysterious audio tapes" with lingering doubt.
The Trump Organization, Donald Trump, and his children Ivanka and Donald Jr. aggressively marketed the Trump Ocean Resort in Baja, Mexico as a transformative luxury development. The project was promoted as part of the "Trump Portfolio" with Trump himself appearing in promotional videos saying "I am very, very proud of the fact that when I build I have investors that follow me all over." Ivanka claimed in marketing materials that she was personally buying a unit.
After the 2007 Wall Street crash, buyers received devastating news: neither Trump nor the Trump Organization were actually developers or investors-they had merely licensed the Trump name to the real developers. Outraged buyers filed lawsuits alleging fraud, misrepresentation, and unfair business practices. Similar licensing deceptions occurred with Trump projects in Waikiki and Tampa, where buyers only discovered Trump wasn't the developer in "micro-script that can barely be read without a magnifying glass."
11장
The Making of a President: What It All Means
No book could capture Donald Trump's entire seventy-year life, but Johnston has focused on aspects of his conduct most relevant to voters, drawing from direct knowledge and thousands of collected documents spanning decades of business dealings and public appearances. The pattern that emerges reveals Trump's obsession with money and wealth, evidenced by his constant references to his net worth and his tendency to inflate his financial success. His objectification of women, demonstrated through numerous documented comments and actions at his beauty pageants and in business settings, along with his extensive relationships with criminals-con artists, swindlers, mobsters, and drug traffickers-paint a complex picture of his character and associations.
Trump's constant attacks on journalists and threats to sue help shield him from scrutiny, a tactic he's employed consistently since his early days in New York real estate. He regularly files lawsuits against critics and journalists, often not to win but to drain their resources and discourage future scrutiny. He dismisses those who don't see him as he sees himself-the mark of a world-class narcissist-and has consistently shown an inability to accept criticism or acknowledge mistakes. His ability to deflect criticism, rewrite history, and project an image of success despite numerous failures and ethical lapses has been the defining characteristic of both his business career and his political rise, from the bankruptcy of his Atlantic City casinos to his controversial Trump University venture.
What emerges from Johnston's decades of reporting is a portrait of a man who has masterfully crafted his own mythology through careful media manipulation and brand building. He's a figure who values revenge over reconciliation, as demonstrated by his public feuds and refusal to apologize, appearance over substance, shown through his focus on ratings and crowd sizes, and personal loyalty over ethical conduct, evidenced by his treatment of both allies and opponents. The question for voters becomes whether the qualities that made Trump a controversial but sometimes successful businessman-his aggression, showmanship, and willingness to push legal and ethical boundaries-are the same qualities needed in a president of the United States.
As Johnston notes, Trump is compelled by money; while others might value honor, he sees wealth as the ultimate measure of success. This fundamental difference in values has shaped his decision-making throughout his career. Once lost, honor might never be regained, while more money can always be earned-a philosophy that has guided his numerous business reinventions and comebacks. The making of Donald Trump reveals not just the creation of a business empire built on licensing deals and media attention, but the careful construction of a persona that has proven remarkably resilient despite decades of controversy, questionable dealings, and broken promises, from contractor disputes to political reversals.
