The Big Why: What’s behind Donald Trump’s apparent self-sabotage?

His escalating threats of violence and spiraling out of control leave more questions than answers

By Lucian K. Truscott IV


Published July 22, 2023 7:00AM (EDT)

Donald Trump (MANDEL NGAN/AFP via Getty Images)
Donald Trump (MANDEL NGAN/AFP via Getty Images)

Here's a guy, he's in his late 20s, maybe early 30s, he owns a big hotel in midtown Manhattan, he's a millionaire many times over, he's in the papers so much that he's famous just for being who he is, he can have anything he wants in life, he can have any woman he wants. He's on a cross-country flight from L.A. to New York seated in first class next to an attractive woman. So what does he do after they have the first-class dinner service seated side by side?

He leans over, and without asking or even saying a word, he starts kissing her on the mouth and groping her breasts. When he takes his hand and starts reaching up her skirt, the woman picks up her purse and flees through the drawn curtains into the coach cabin.

When several years later he sees the woman at a big charity event in Manhattan, what does he do? Does he turn away and try to avoid her for the rest of the evening? Does he leave the event? No, he strides right up to her and with people all around them in their evening finery, he calls her a "cunt."

He was Donald Trump, of course.

It was the late 1970s. He had a wife and children. He owned real estate all over the New York City boroughs of Queens and Brooklyn. He owned the Miss Universe pageant, where dozens of beautiful young women competed for his attention. If he wanted to be unfaithful to his wife, he could simply pick up the phone and have, as it was said, any woman he wanted. With all his money, all his fame, all the attention he got on a daily basis for doing ordinary things like having dinner at a restaurant or appearing at a nightclub or even walking down the street, why did a man who didn't know the woman sitting next to him on a commercial airplane, in full view of the other passengers and flight attendants, grab her breasts and then attempt to grab her "pussy," as he would later describe the same act when speaking to a reporter for a major television program?

We need your help to stay independent

Years later, while running for the presidency of the United States, 25 other women would accuse him of similar behavior. He knew only one of them personally, his ex-wife, who accused him of marital rape. The others he either didn't know or were casual acquaintances. Many of the acts of sexual assault, like his rape of E. Jean Carroll in the dressing room of a Manhattan department store, were committed either in full view of other people or in public places.


He has to know that the only effects of his personal attacks will be negative.

That has always been the question about this man, hasn't it? We're going to get into what might be called The Big Why in a moment – why he has risked his own freedom by allegedly committing multiple felonies trying to overturn an election he knew for a fact that he had lost, why he took hundreds of classified documents from the White House when he left office and mishandled them and then tried to cover it all up from the FBI and the Department of Justice (DOJ). But for right now, let's consider these other why's, because he did the same thing he did on the airplane again and again throughout the decades that followed. They were sexual assaults, and he's alleged to have committed most of them in public.

In a New York nightclub in the early 1990s, Trump put his hand up the skirt and touched the vagina of the woman sitting next to him. He wasn't talking to her at the time, and she didn't even realize it was Trump who was sitting next to her until he assaulted her.

At his club, Mar-a-Lago, also in the early 1990s, he pushed a woman who was working for him against the wall and forcibly kissed her and put his hand up her skirt and groped her.

In the late 1990s, Trump groped and forcibly kissed a woman who was sitting in his VIP box at the U.S. Open tennis tournament and held her arms and body so tightly, he prevented her from leaving the box and getting away from him. The next year, in the parking lot of the same tennis tournament, Trump approached a woman he didn't know and groped her as she was waiting to be picked up by a car.

In the early 2000s, Trump grabbed a guest at his Mar-a-Lago New Year's Eve gala and pulled her behind a set of curtains and forcibly kissed and groped her breasts and grabbed her pubic area.

In 2005, Trump took a reporter for People Magazine who was interviewing him into an empty room at Mar-a-Lago and forcibly kissed and groped her and told her he wanted to have an affair with her.

Every person with his or her head screwed on right has an instinct for self-preservation — but not Trump.

We could go on. It was the same thing again and again, sexual assaults of women he either didn't even know the name of or was casually acquainted with, like the People Magazine reporter or the guest in his U.S. Open VIP box. And the question is the same: Why?

It's not good enough to speculate that he had an excess of testosterone or an elevated sex drive.  Lots of men have both of those things and do not commit sexual assaults. And almost none of the sexual assaults described by any of the women ended with an actual act of copulation. The assault was the point, not the sex. So, is he just a serial sexual assaulter, like a serial rapist who can't stop himself from committing the same crime over and over?

I don't think so. How do you explain his association or friendship or whatever it was with Jeffrey Epstein? Trump didn't have an apparent fascination with or attraction to underage girls. Several of the women he assaulted were middle-aged. He didn't need Epstein to provide him with targets  Women to assault were all around him. His habit was to just pick one and assault her right there on a plane or in a nightclub or follow her until he could get her in another room or behind a curtain or, in the case of E. Jean Carroll, in a public dressing room, where he assaulted them.

The only pattern was repetition. He explained on the "Access Hollywood" tape that "when you're a star, they let you do it. You can do anything." But they didn't let him do it. He did it without asking. They were not sexual approaches, or sexual flirtations, or sexual seductions. They were sexual assaults.

Want a daily wrap-up of all the news and commentary Salon has to offer? Subscribe to our morning newsletter, Crash Course.

There is a "because I can" aspect to the attitude he evinced on the "Access Hollywood" tape, and that attitude permeates more about his life than his sexual assaults. Trump did things just because he could all the time. He bought the Plaza Hotel in 1988 because he could. He took out loans to do it, of course, and that purchase would go on to lose him about $400 million. Other gambits he engaged in, like his Atlantic City casinos, would cause him to declare six bankruptcies, so it was the banks who lost money, not Trump.

For many years, he got away with what amounted to a series of financial crimes because he could, at least until Manhattan District Attorney Alvin Bragg indicted him in April on 34 counts of falsifying business records stemming from the hush-money payments to Stormy Daniels all the way back in 2016. Those charges, while they don't address the rest of Trump's business scams, such as underestimating property values for insurance purposes and overvaluing them when seeking to use property to secure loans, are serious enough that he goes to trial on the New York charges on March 25, 2024. That trial will follow a second trial for damages in a follow-up lawsuit filed by E. Jean Carroll set to take place in December of this year, and it will precede by two months the trial date set on Friday by Judge Aileen Cannon on the 31 count indictment charging Trump with violating the Espionage Act for the removal of classified documents from the White House, as well as six counts of conspiracy to obstruct justice in the same matter.

And so we find ourselves asking — again — The Big Why.

Why did Trump allegedly commit so many crimes trying to overturn an election he had been told by his own campaign that he lost, that his loss of 61 trials challenging the election results proved that he lost, and that he apparently knew himself that he lost, at least according to reports of prosecutors' interviews with witnesses close to Trump in November of 2020 right after the election had been called for Joe Biden? The whole "stop the steal" business was law breaking based on lies that he knew were lies. If he knew he had lost the election, why risk getting caught for breaking the law so many times? And yet like a serial killer who escalates his crimes over the years in frequency, brutality and risk, Trump forged ahead with one scheme after another. It was, in the end, law-breaking for the sake of law-breaking. 

Imagine yourself in the Oval Office with Rudy Giuliani, John Eastman and Jeffrey Clark. Would you listen to the likes of those three?  Jeffrey Clark, who ran the DOJ environment division, was made fun of in front of the president by his DOJ superiors, who told Clark something like, we'll ask your advice when we have problems with a farm pond. Remember Eastman's get-up on Jan. 6 when he addressed the crowd at the Ellipse near the White House, in some kind of louche cowboy hat and silk scarf? How about New York City mayor turned Trump adviser Rudy Giuliani with hair dye running down his face? They were absurd characters. Listening to them was like taking a tip from a tout to bet on a lame horse.

And now that he is already under indictment by special counsel Jack Smith on the documents case, Trump has kept up with his attacks on Smith, calling him "deranged" in a statement about the target letter he received from the office of the special counsel. Trump cannot think the personal attacks on the man prosecuting him on one indictment will get him anywhere with potential charges for his attempts to overturn the election. He has to know that the only effects of his personal attacks will be negative. 

Then why? The theory that his real defense against the charges against him is to win the election for president doesn't account for the fact that he will go on trial in the documents case next May, and there is a strong possibility that he will be charged in Georgia and face a trial in that state before next November. Nothing Trump is doing is helping him or his lawyers in his defense against any of the charges he faces.

Every person with his or her head screwed on right has an instinct for self-preservation — but not Trump. Every door he opens leads not to a dead end but to a worse place. The motion to dismiss the latest case filed by E. Jean Carroll just gave the judge the chance to write a 59-page decision calling him a liar and a cad and explaining that despite the verdict in the last case, Trump raped Carroll. So why does he keep testing fate?  



The juvenile instinct to do something bad in order to get caught?

Armchair psychoanalysts and real ones both have been trying to read this guy's synaptic tea leaves for years and still the question, why, is unanswered. The fact that he has not until now faced consequences for so many of his actions, from sexual assaults to financial crimes to two impeachments for violations of the Constitution, certainly explains at least some of his serial crimes. It's tempting to think that he has become more irrational as he feels the law's grip, but when you think back to a cross-country flight in the early 1970s and what he did to the random, innocent woman seated next to him, you realize that measuring the level of his irrationality is like measuring his girth: It just grows and grows.

By Lucian K. Truscott IV

Lucian K. Truscott IV, a graduate of West Point, has had a 50-year career as a journalist, novelist and screenwriter. He has covered stories such as Watergate, the Stonewall riots and wars in Lebanon, Iraq and Afghanistan. He is also the author of five bestselling novels and several unsuccessful motion pictures. He has three children, lives in rural Pennsylvania and spends his time Worrying About the State of Our Nation and madly scribbling in a so-far fruitless attempt to Make Things Better. You can read his daily columns at and follow him on Twitter @LucianKTruscott and on Facebook at Lucian K. Truscott IV.

MORE FROM Lucian K. Truscott IV

Related Topics ------------------------------------------

Commentary Donald Trump Trump Crimes