Donald Trump’s Life of Failure and the Art of the Pivot
The Apprentice received significant attention for portraying a young real estate heir’s transformation into the gargantuan sociopolitical brand we have come to know as Trump. Roy Cohn, one of the most powerful lawyers in the history of New York, was a character who shaped the business philosophy of the future president. One of the first things the audience sees is Cohn teaching Trump his three rules for winning. Rule one was “attack, attack, attack.” Rule two was “deny everything.” Rule three was “no matter what happens, never admit defeat.”
David L. Marcus, a journalist and — regrettably, in his eyes — cousin to Cohn, wrote a piece for Forward in reaction to the film, describing it as “chillingly accurate.” In particular, he singled out those three golden rules as making up a very real philosophy that Cohn followed intently. When surveying Donald J. Trump’s history as a public figure, his application of this philosophy is apparent.
Trump has had a pervasive impact on America, as a citizen and as a president. It’s impossible to completely reduce Trump to one quote, one story, or one statistic, but there are a few memorable moments that have shaped Trump’s place in American culture, and one instance that particularly stands out is from just last month.
It was a sunny afternoon in our nation’s capital. A gaggle of reporters had congregated in front of a lineup of Teslas. The CEO of the EV manufacturer, Elon Musk, stood proudly in front of the vehicles, but he was not the initial focus of the press. Another man swayed beside Musk, giving what can only be described as a sales pitch. “It’s a great product,” he said, “as good as it gets!” He continued, excitedly sharing his desire to purchase one of the cars, and even remarked on how he already bought a Tesla Cybertruck for his granddaughter. The salesman touted the benefits of the vehicle, calling it “safe” and “strong” and noting its stainless steel–plated exterior. “I happen to love the product,” he said. He closed his pitch by commenting on the Cybertruck’s price of $35,000—it is, in fact, more than twice that number—before passing the baton to Musk.
That salesman was Donald Trump. In reality, this was a press conference in front of the White House just 3 weeks ago. Almost every question reporters asked was redirected back to Tesla's current importance to America and the future of the company.
Donald Trump has always been a salesman at heart, and like any good salesman, he has no problem shifting what and how he sells, even when he’s been met with failure. The pivot has always been a crucial element to his non-political career. Many such pivots can be found in his numerous ill-fated attempts in the 1980s and 90s to get tax breaks for gratuitous projects such as the revealingly named “Trump City.” Over the years, he has become particularly adept at flipping his failures into victories.
The cult of personality around Trump is a clear result of his ability to turn his short-term losses into long-term wins. For example, that “Trump City” project? It ultimately failed slowly and painfully, due to conflicts with the community surrounding the build site and then-New York mayor Ed Koch. But Trump’s pivot from this project represents a turning point in his life.
This failure of what a 1985 New York Times op-ed deemed “his bid for immortality” made Trump’s vulnerability at the time all the more clear. By the 1990s, he was over $3 billion in debt — mainly from the loans he used to fund his failed Atlantic City casinos. Backed into a corner and with nowhere to go, Trump compromised on Trump City, acquiescing to city demands for reduced scale and more citizen-friendly architecture.
It was a business disappointment but a massive boost to his reputation, which had been historically marred by marriage scandals and misgiving about his financial situation. The public rehabilitation that this compromise provided, despite the fact that it was essentially his only choice, was key to launching him into reality TV stardom as the host of The Apprentice.
Another example of a famous pivot was how Trump navigated one of his most enduring ambitions. A common thread that ran through his real estate career, TV career, and the beginning of his political career was Trump’s desire to own a team in the National Football League. In the early 80s he attempted to acquire the Baltimore — now Indianapolis — Colts twice and at times expressed interest in the Dallas Cowboys.
When all three ventures crashed, Trump decided to take an alternative path to NFL ownership. He invested in the New Jersey Generals of the new, up-and-coming United States Football League and set the league on a collision course with the NFL by pushing to play in the fall instead of the spring.
Moving to the fall resulted in an antitrust lawsuit against the NFL. Trump led the charge, encouraging a merger so he could gain access to the NFL franchise he so desired. The trial ended in a technical victory for the USFL, but the jury only awarded three dollars and seventy-six cents in damages, and the league folded soon after. The NFL had violated antitrust laws, but the USFL’s growing financial issues were mostly self-inflicted.
Even after he essentially destroyed the USFL, Trump’s pursuit of an NFL continued for three more decades. A failed attempt to acquire the Buffalo Bills in 2014 may have been what pushed Trump — who had expressed a passing interest in public office in the 1990s — to fully pivot to positioning himself for a presidential run.
It’s impossible to fully essentialize his shocking wins in 2016 and 2024. However, it’s fair to say that one reason for his control over his base is how he has used almost every criticism against him to ignite a persecution complex among a certain subset of voters. Trump has had a consistent answer to every indictment, every unseemly, displeasing quote, and every federal court injunction. Essentially every single failure he has been confronted with, he has presented a defensive response. His go-to retorts include “fake news” or a claim of “the deep state” scheming to undermine him.
The image of himself that Trump has implanted in his supporters, of a man crusading against dark forces, is a particularly attractive idea for conservative Christians, his strongest supporters. A 2016 pre-election report from the Public Religion Research Institute and the Brookings Institution found that three-quarters of Republicans and almost 80 percent of Protestant evangelicals believe that Christians face just as much a discrimination problem as racial minorities do. In effect, Trump has managed to tap deep into his base’s already existing persecution complex, feeding off of it.
Trump has been able to turn the greatest defeat of his entire life into the highest favorability of his political career. Everyone knows this one — Trump lost the election in 2020, then claimed he didn’t. Most of his supporters bought the lie, not because the evidence was on his side — it wasn’t — but because it played into the image of Trump as a martyr. The implicit message Trump sent with his election denial was that they screwed me, and they’ll screw you too.
“The Big Lie,” as it has become known, served its purpose. It’s doubtful that Trump, even with the immense amount of audacity the man has, truly believed that he could successfully challenge the election results. However, the message that the election was rigged became the single greatest piece of evidence of the establishment going out of their way to undermine Trump. Since his loss in 2020, Trump’s favorability rating has reached its highest level since his inauguration eight years ago.
In order to attack Trump’s character, actions, and policies, his opponents must understand that it’s not enough to simply list his failures. He will squirm, spin, and blame his way out of whatever is thrown at him. The only way to overcome Trumpism, as a country, is to address the real issues that non-MAGA voters chose him for. For example, union members and Latino voters are two groups who clearly felt disenfranchised by the Democratic Party, so this year they switched parties. Successful opposition of Trump-endorsed GOP candidates in the 2026 midterms should and will need to focus on a disastrous first term riddled with authoritarianism. However, opposition must also present something tangible to voters, not just a movement to normalcy, but a movement towards a better America — a movement away from the country that created Trump.