What 'The Apprentice' Gets Right (And Wrong) About The True Story

Answer: According to him, no; according to everyone who knew him, yes.

The Full Story: Cohn was famously bigoted and “anti” the very things he himself was. POLITICO's Michael Kruse described Cohn as: 

[A] lawyer who hated lawyers, a Jewish person who hated Jewish people, and a gay person, fiercely closeted if haphazardly hidden, who hated gay people.

In addition to his espoused homophobia, Cohn actively fought against gay rights. To those who knew the truth, he rationalized that while he slept with other men, he was too powerful to be classified as gay. And when he was diagnosed with HIV, he pretended it was liver disease. 

According to a former boyfriend Wallace Adams:

Even at the end, he refused to admit that he was gay, and he refused to admit that he had AIDS.

Answer: Yes, though at a different time than the movie showed.

The Full Story: One of the most heartbreaking moments in The Apprentice occurs during a dinner at Mar-a-Lago, when the ailing Roy Cohn proudly tells Ivana that Trump gave him diamond cuff links - only for her to inform him they’re cheap knock-offs.

While the timing and delivery of this news was fictionalized - Cohn wasn’t informed by Ivana Trump during a dinner at Mar-a-Lago - Trump did gift his lawyer “a pair of diamond-encrusted cuff links and buttons in a Bulgari box,” on a different occasion, after a big legal win.

It’s doubtful Cohn even knew the cuff links were fake, though; his lover, Peter Fraser, revealed this after having them appraised following Cohn’s passing.

Answer: Basically, yes. Roy Cohn had a three-part philosophy for success similar to what he tells Donald Trump in The Apprentice, if not verbatim.

The Full Story: In The Apprentice, Roy Cohn passes along a three-point success strategy “for winning” to young Donald Trump, which we see Trump adopt and parrot by the end of the film: 

(1) Attack, attack, attack; (2) admit nothing, deny everything; and (3) no matter what happens, claim victory and never admit defeat.

The words may vary slightly, but the sentiment holds true to what Cohn preached in real life. According to author Sam Roberts: 

Roy was a master of situational immorality… He worked with a three-dimensional strategy, which was: 1. Never settle, never surrender. 2. Counter-attack, counter-sue immediately. 3. No matter what happens, no matter how deeply into the muck you get, claim victory and never admit defeat.

It probably will sound familiar to anyone who's watched Trump's political career, and that's probably because Cohn did sign on as Trump's lawyer on a lawsuit in the '70s, and he did develop a close relationship with Trump, who became something of a protégé. 

Cohn, a man described as snakey, savage, amoral, abrasive, and “a new strain of son of a b*tch,” earned his own rise to power through his aggressive “by whatever means necessary” approach, unabashedly throwing out ethical and legal considerations. Cohn and Trump were undoubtedly close, and many would (and do) argue, as The Apprentice does, that Cohn was the pivotal influence of Trump becoming Trump. As columnist Liz Smith put it, “Donald lost his moral compass when he made an alliance with Roy Cohn.”

But of course, whatever historians or filmmakers may surmise, it's impossible to know the exact level of influence and impact Cohn had on Trump. It was famously reported, however, that amidst a flustering moment in his presidency, frustrated with the lack of efficient, trustworthy advisors, Trump asked, “Where's my Roy Cohn?”

Answer: Yes. While we don’t know the entire ins and outs of Donald and Ivana Trump’s courtship and whirlwind engagement, what we do know lines up with many elements shown in The Apprentice, specifically regarding the prenup.

The Full Story: Ivana Zelníčková was in New York with a group of models when Trump first spotted her at Maxwell’s Plum, a famous bar, and used his pull to get her a table. The following year they signed an “antenuptial agreement” and married that April.

Roy Cohn was on the scene with an “onerous prenup,” though in reality Ivana had a lawyer present as well. Screenwriter Gabriel Sherman says, however:

It was a lawyer that Roy arranged to have for her. So the lawyer was basically in on it with Roy. It was so corrupt.

As for the fight about a line that insists she’s to give back all gifts in the event of their divorce, according to Ivana’s 1990 divorce deposition, this was present in an early draft of the agreement, and Trump had to chase her out to the sidewalk and convince her to return. According to The New York Times:

Sensing her sorrow, Mr. Trump apologized, Ivana Trump later testified in a divorce deposition. He said it was his lawyer’s idea. “It is just one of those Roy Cohn numbers.”

As for the rest of their marriage, friends of the couple speak to a deterioration similar to what’s shown in the movie - as Ivana became more helpful as a business partner, Trump’s romantic interest dwindled, and he may have been jealous of his wife’s success:

Donald thought he made her. He put her there, but he couldn’t stand it. The student surpassed her master.

Answer: Yes. Frederick “Freddy” Trump Jr., Donald’s older brother, passed of a heart attack linked to alcoholism at age 42.

The Full Story: As the eldest son, Fred Jr. was expected to fill his father’s shoes in the real estate business, but chose to be a pilot instead. As shown in the movie, this did cause tension in the family, specifically with Fred Sr. and Donald, with the Trump patriarch labeling his son “a chauffeur in the sky," and his younger brother reportedly telling him “you're wasting your time.”

Donald Trump admitted as much in various interviews, telling Playboy in 1990, “Our family environment, the competitiveness, was a negative for Fred.” He reflected in a CBS interview the same year:

Perhaps it was my fault and perhaps my father’s fault for egging him on to business because he wasn’t good at it, because he didn’t like the business.

Freddy Jr. married and had children, but after developing alcoholism in the ‘60s, by the ‘70s he stopped flying, got divorced, and moved back in with his parents before his passing in 1981. Trump has cited his brother’s alcoholism as impactful to his life and a reason he doesn’t drink, while according to Freddy’s friends:

The president has too often told the story in a way that put Fred Jr. in the harshest light while painting himself as the virtuous brother who avoided alcohol.

The Apprentice shows Trump turning away his brother in his hour of need. Trump has stated that he would visit with his brother during his final years but that “there [wasn’t] much we could do at the time.”

Mary Trump, one of Freddy’s two children, has described her grandfather as a “high-functioning sociopath” and said Donald Trump was seeing a movie the night his brother passed. Mary and Fred III have a fraught relationship with the family after being cut out of their grandfather’s will and ensuing legal battles.

Answer: Yes. Donald Trump, his father, Fred, and Trump Management were sued by the federal government for racial discrimination in their New York housing developments.

The Full Story: In 1973, the Justice Department brought a lawsuit against the Trumps based on evidence gathered by testers for the New York City Human Rights Division. The testers would investigate racial bias by seeing if white customers seeking a service would receive the same treatment as someone of color who was denied. In this case, a Black man apartment hunting was told the unit was no longer available, while the white tester was shown the apartment. Further investigation suggested building superintendents were turning down Black tenants at the behest of Trump Management.

After a two-year legal battle, the government offered a settlement, which the Trumps accepted. (While the film shows this as a win after bringing Cohn into the fold, it was actually a slightly worse settlement than the Trumps were first offered.) It required them to take actions to welcome Black applicants and familiarize themselves with the Fair Housing Act, though they did not have to admit wrongdoing, a point Trump mentioned when the case was brought up in the 2016 presidential debate:

Yes, when I was very young, I went into my father's company — had a real estate company in Brooklyn and Queens… And we, along with many, many other companies throughout the country — it was a federal lawsuit — were sued. We settled the suit with zero, with no admission of guilt.

According to Washington Post reporter and Trump biographer, Michael Kranish, while there were other cases brought, the lawsuit against the Trumps specifically was “one of the largest cases of the time” and one that was not easy to fight. Moreover,

It was a suit that was directly against them, and it is one that Donald Trump to this day clearly is upset about.