Pre-Election Trump

For a more detailed list of Trump's major business failures, please see the "Major Fails" section.

School Years

(Page numbers refer to: 'Trump Revealed' by Michael Kranish and Marc Fisher. (WaPo))

  • Childhood neighbor in Jamaica Estates recalls seeing Donald jump off his bike one afternoon and pummel another boy. (Kranish, p.34)
  • As a second grader, Donald admits punching his music teacher Charles Walker in the face because “I didn’t think he knew anything about music.” (p.34)
  • In military academy as a teenager, once grabbed a boy named Ted Levine and tried to shove him out of a second-story window, but two other cadets intervened. (p.42)
  • To avoid service in the Vietnam War, achieves four draft deferments, the first of which was given on July 28, 1964. (p.45)
  • In college, drove his squash teammates to games in his sports car, but required them to chip in for gas even though the coach gave Donald gas money. (p.46)
  • Despite claiming being a top student at Wharton School of Business, was never listed in the honor roll printed in the Daily Pennsylvanian school newspaper. “I don’t think he ever studied for an exam,” said Louis Calomaris, a classmate. (pp.47-48)
  • 1973 Gets sued by the Justice Department for systematically discriminating against blacks in 39 different buildings. Under the advice of Roy Cohn, countersues the government for $100 million. (Salon) Settles out of court two years later without admitting guilt. (NYT) Admits to destroying company documents while under subpoena to save space. (PoliticusUSA) In Feb 2017 FBI releases hundreds of pages of notes from the investigation. (the notes via

Slumlord Years     

(Pages numbers refer to Trump Revealed by Michael Kranish and Marc Fisher)     

  • 1971 At age 25, becomes president of Trump Management, overseeing the rent collection and management of fourteen thousand apartments throughout the New York City outer boroughs. (p.52)
  • October 1973 Donald and father sued by the Justice Department for a “constant pattern and practice of discrimination,” basing residential availability and pricing on race. (p.57) Settles the case after two years and forced to change their practices. (p.67)
  • 1975-1978 Accosted along with father by the Justice Department for not complying with the 1975 settlement regarding racial discrimination of renters. (pp.68-69)
  • 1976 A New York Times profile claims that Donald is worth more than $200 million, whereas he reported an income that year of $24,594 and owed $10,832 in taxes. (p.69)
  • 1985 Sued by New York City for using illegal tactics to force tenants out of a property he intended to demolish. (source) Settled out of court ten years later. (Wikipedia)

Manhattan Years   

  • 1973-1986 Trump grows close to client, mentor and close personal friend Roy Cohn, who: (NYT)
    • Served as Senator Joseph McCarthy's Red-baiting attorney (1952-1954).
    • Prosecuted Julius and Ethel Rosenberg of espionage, wherein they were executed by electrocution.
    • Represented crime boss Anthony (Fat Tony) Salerno.
    • Introduced Trump to the social and political elite of Manhattan.
    • Spoke with Trump by phone up to five times each day, and taught him to viciously counterattack every attack.
    • Arranged a prenuptial agreement between Trump and his first wife Ivana Winklmayr that was later ruled invalid due to lack of proper legal representation for Ivana.
    • Helped Trump obtain zoning variances and tax abatements critical to the Grand Hyatt Hotel and Trump Plaza. Trump awarded him with diamond cufflinks that were later discovered to be fake.
    • Disbarred for flagrant ethics violations weeks before his death in 1986, including improperly coercing a multimillionaire client on his death bed to amend his will make Cohn executor.
  • 1988 Sued by the Justice Department for stock purchase violations. Pays $750,000 to settle. (Wikipedia)
  • 1988 Purchases Eastern Air Shuttle, an airline composed of 17 Boeing 727s, and rebrands it Trump Airlines. It defaults on its debts in 1992. (BostonGlobe)
  • 1989 Spends $85,000 in four major papers calling for the state execution of five black suspects in a Central Park rape, and says that everyone should share his hatred for them. (NYT)
  • 1990 Is sued for $2 million by a business analyst and settled out of court. The analyst predicted the demise of Trump’s Taj Mahal and Trump coerces his firm to fire him. The analyst’s firm is forced to pay him $750,000 and Trump also pays him an undisclosed amount in a settlement. (NYT)(
  • 1991 Fined $230,000 when it is discovered that Trump’s father bought $3.5 million in chips he gave to his son Donald as an “interest-free loan.” (WaPo)
  • 1992 Wins a gag order enforcement suit against ex-wife Ivana, whose memoir details his forcible assault and rape of her during their marriage. (
  • 2000 Pays $250,000 in fines to the NY State Lobbying Commission for illegally lobbying against plans for an Indian-run casino that would have competed with his casinos. (NYDailyNews)
  • 2001 Cited by the Securities and Exchange Commission for a financial-reporting case involving misstated earnings from Trump Hotels and Casino Resorts, Inc. (
  • 2008 Approached by Deutsche Bank for a $40 million personal guarantee by Trump on a $640 million loan. Trump responds by suing Deutsche Bank for $3 billion. Deutsche Bank then sues Trump for the $40 million and they settle out of court with a loan extension for Trump. (Wikipedia)(Atlantic)
  • 2008 Sues a small town in California for $100 million for fraud and civil rights violations when his luxury home and golf course development shows to be prone to landslides. (LATimes) He withdraws the suit in 2012 for multiple permit concessions. (
  • 2009 Sues a former law firm for $5 million for them mentioning his name and providing links on their website. Suit is dismissed. (PublicIntegrity)
  • 2009 Sued by investors of condos at Trump Ocean Resort Baja Mexico, which failed to launch. Trump disavows responsibility since he was only the spokesperson and brand behind the project. (LATimes)(NYTimes) He settles with over one hundred plaintiffs in 2013. (Wikipedia)
  • 2010 Sues Palm Beach County over airport noise near his Mar-a-Lago estate and loses. (Wikipedia)
  • 2011 Sues the nation of Scotland for building a wind farm near a golf course of his. Loses the suit in 2015. (WSJ)(BBC)
  • 2015 Sues Palm Beach County over airport noise near his Mar-a-Lago estate for the third time. (USAToday)
  • 2015 Sues the town of Ossining, NY to devalue a property he reported to the FEC as being worth $50 million. He seeks a $1.4 million valuation as to reduce his property tax bill by $424,000. (Guardian)
  • 2011 Decision is upheld to dismiss Trump’s $5 billion defamation suit against a book author who claimed in TrumpNation that Trump was only worth between $150-$250 million. (NYTimes) The appellate court cited probability of truthfulness as the basis for dismissal. (HollywoodReporter)
  • 2011 After filing his fourth bankruptcy, says “I do play with bankruptcy laws – they’re very good for me.” (Newsweek)
  • 2013 Sues Bill Maher for $5 million after producing his birth certificate. Maher had challenged him on Jay Leno that he (Maher) would pay $5 million if Trump could prove his mother had not mated with an orangutan. (Forbes) He drops the suit two months later. (Reuters)
  • 2014 Settles $5 million arbitration with former beauty pageant queen Sheena Monnin after she alleged that the Miss USA 2012 pageant was rigged. As part of the settlement, Monnin was not required to retract her statement. (DailyBeast)
  • 6/23/14 Expresses outrage that the Central Park Five suspects (see 1989) settled a wrongful conviction settlement for $41 million, tweeting "Tell me, what were they doing in the Park, playing checkers?" (NewYorker)(HuffingtonPost)(op-ed by Trump)
  • March 2016 Sued under a class-action for severely underpaying up to 250 foreign fashion models hired by Trump Model Management and another Trump company. (CNN) The class action could expand by another 750 workers to include waitresses, cooks, vineyard workers, laborers, managers and superintendents, 850 of which are from Mexico. (Reuters)
  • As of 2016 Trump and businesses have been involved in about 3,500 legal cases: (USAToday)
    • 1,900 Trump and/or company as Plaintiff
    • 1,450 Trump and/or company as Defendant
    • 150 Third party, filer of bankruptcy or other
    • Named personally in 169 suits in federal court
    • 500 cases dismissed against Trump in civil court
    • 451 wins, 38 losses, hundreds more unclear from public record