WASHINGTON — During the debut episode of “The Apprentice” in January 2004, Donald Trump made a rare admission he would be unlikely to repeat today.
“It wasn’t always so easy,” Trump narrated in a voice-over, acknowledging that during the late 1980s, “I was seriously in trouble” and “billions of dollars in debt.”
This represents one of the rare occasions when Trump has publicly recognized failure. However, even then, he was following a script designed to showcase his comeback story for television audiences, foreshadowing the confrontational appeal that would fuel his political ambitions years later.
“I fought back,” Trump declared. “And I won. Big league.”
According to Trump’s narrative, he never experiences defeat.
He proclaimed success just days after the Iran conflict began and continued making such claims throughout the crisis, even as Tehran launched attacks against American and allied forces while blocking the Strait of Hormuz, creating worldwide economic disruption.
Now that a ceasefire has been established, Trump maintains the United States achieved its objectives.
The president is celebrating a leadership transition following the death of Iran’s supreme leader, Ayatollah Ali Khamenei. However, his replacement is his son, Mojtaba Khamenei, who holds more extreme positions. While Trump insists Iran will be prevented from obtaining nuclear weapons, Tehran continues to maintain uranium stockpiles. The strait is reopening, but under Iranian military oversight.
After The Wall Street Journal’s editorial board criticized Trump for declaring premature success in Iran, the president responded on social media Thursday, stating, “Actually, it is a Victory.”
On Saturday, he posted that media outlets “love saying that Iran is ‘winning’ when, in fact, everyone knows that they are LOSING, and LOSING BIG!” When questioned later about ongoing Iranian negotiations, Trump replied, “Regardless what happens, we win.”
This tendency to claim victory has characterized Trump’s mindset since his youth as a New York property developer. The pattern continues across both significant and minor matters.
From golf tournaments at his properties where he consistently emerges as champion, to unfavorable court decisions he portrays as favorable, to business deals he announces but never finalizes.
“He has this fictional narrative in his head” and is “like a screenwriter,” explained David Cay Johnston, who wrote “The Making of Donald Trump.” “When you need to change the narrative, you just change it.”
The most dramatic example remains Trump’s refusal to accept his 2020 election loss to Democrat Joe Biden, despite confirmation through more than 60 court cases and his own attorney general. Yet Trump’s repeated victory declarations have convinced his supporters. He understands the influence of persistence and volume.
This defines Trump’s reality — as both promoter and president, crafting his narrative and others’, using slogans throughout his second term. One baseball cap he wears and sells summarizes this philosophy in five words: “TRUMP WAS RIGHT ABOUT EVERYTHING.”
“It’s much easier to lead when you’re successful and you’re winning,” Trump told a recent Saudi investment conference in Florida, where he also mentioned, “I always like to hang around losers, actually, because it makes me feel better.”
“People follow you if you win,” Trump added.
While White Houses have traditionally attempted to present negative developments positively to minimize unfavorable political assessments, Trump has elevated constant winning as central to his presidency.
When the Supreme Court overturns his key tariff policies, Trump promises to circumvent the decision so his import taxes can be “used in a much more powerful and obnoxious way, with legal certainty.” When promised American investments he promoted fail to materialize, he simply claims they occurred while sometimes exaggerating their imaginary value.
His Justice Department initially stopped challenging court rulings that blocked executive orders targeting major law firms, then reversed course because failing to appeal might appear as accepting defeat.
This alternative approach has become both a governing philosophy and a Trump family principle.
Eric Trump, one of the president’s sons, stated his father “has never needed to project a ‘winning image.’”
“He IS the definition of a winner,” the younger Trump declared in a statement, “based on what he has built and accomplished.”
Sarah Matthews, a former deputy press secretary from Trump’s first term who resigned following the January 6, 2021 Capitol riot by Trump supporters, said the president’s “ego won’t allow him to acknowledge defeat” and that “reality just kind of bends” to accommodate it.
“That was the messaging strategy,” Matthews explained. “It was, ‘How can we redefine this loss as a victory?’”
She admits regret now, but explained that previously, there was “always a way to find an excuse to justify that loss and defend his position.”
Recently, Trump’s second-term administration celebrated his first year back in office by compiling “365 wins” across the same timeframe. These included some repetitive and inflated claims while highlighting rising stock markets, declining gas prices, and robust job growth that have largely reversed since the Iran conflict started.
White House spokesman Davis Ingle said Trump “proudly projects the unmatched greatness of our country consistently in his public comments.”
John Bolton served as Trump’s first-term national security adviser and initially supported American and Israeli strikes against Iran. However, he said Trump’s victory declaration regarding Iran was always “baked in the cake” regardless of actual results.
“The world for him is divided into winners and losers,” Bolton observed. “And he’s always a winner.”
In 1973, federal officials sued Trump and his father for alleged racial discrimination in apartment rentals at their Brooklyn and Queens properties. Roy Cohn, the infamous attorney who aggressively promoted Senator Joseph McCarthy’s anti-communist hearings during the 1950s, encouraged the Trumps to file a countersuit.
Both parties reached a settlement two years later that prohibited the Trumps from “discriminating against any person.” The future Republican president called it a victory, emphasizing there was no guilt admission — despite the Justice Department describing the settlement as “one of the most far-reaching ever negotiated.”
Trump first encountered Cohn in 1973 at Manhattan’s exclusive Le Club, and Cohn is credited with teaching key principles, including never acknowledging wrongdoing or defeat and counterattacking anyone who attacks you.
Cohn “taught Donald, you never concede as much as a comma,” Johnston explained.
“Whatever position you’ve taken, that’s the position, and anybody who challenges you, they’re wrong. They’re disgusting. They’re incompetent. They’re idiotic,” Johnston continued. “If they’re law enforcement, they’re corrupt.”
Throughout the years, Trump consistently lost money, launching unsuccessful product lines bearing his name including steaks, bottled water, vodka, a magazine, an airline, a mortgage company, and online education. His Trump Plaza Hotel declared bankruptcy, his New Jersey Generals football team folded, and the Tour de Trump cycling event never became America’s equivalent to the Tour de France.
Barbara Res, who worked at Trump’s company for nearly twenty years, recalls him enjoying creating competition among top executives to ensure he remained the dominant voice, even as losses accumulated.
Regarding today’s Trump, she said, “Nothing is wrong to him, if it helps him.”
“He wasn’t always like that. He understood the difference before,” said Res, author of “Tower of Lies: What My Eighteen Years of Working With Donald Trump Reveals About Him.” “I can’t say why he changed. It could be because he has so much power. Or because he never really believed it.”
None of these setbacks damaged Trump’s self-promoted image as wealthy and famous, which was amplified by the television success “The Apprentice.”
However, Robert Thompson, a Syracuse University professor specializing in television and popular culture, said that success built upon earlier elements, including the appealing arrogance reflected in Trump’s 1987 book title “The Art of the Deal,” his aggressive pursuit of media coverage, and his fixation on naming ventures after himself.
This helped Trump become the “stock character of billionaire,” earning appearances on shows like “The Jeffersons,” “The Fresh Prince of Bel-Air,” “The Nanny,” and the movie “Home Alone 2,” Thompson noted.
“When you need someone to quickly and efficiently represent ‘American Rich Guy,’ Trump has kind of cast himself in that position,” Thompson said, “and everybody goes along with it.”
Trump refused to acknowledge his substantial losses. After his three Atlantic City, New Jersey casinos filed for bankruptcy, he told The Associated Press in 2016 that Atlantic City had been “a great period for me.”
Beginning in 2007, he became regularly involved with WWE executive Vince McMahon, whose wife Linda now serves as Trump’s education secretary. The future president enjoyed dramatic, televised events where his chosen wrestler always emerged victorious.
Trump also started addressing crowds, developing the “sketch and the rhythm” that would later become his political strength, Thompson explained: “The rallies are born in wrestling,” he said.
“Winning is an attitude, not a collection of facts,” Thompson observed. “Winning is, in this case, always defined by the person doing the winning.”
Trump brought this never-lose perspective into his political career.
Following his loss in the 2016 Republican Iowa caucus, he posted that winner Ted Cruz “illegally stole it.” Trump claimed victory in the popular vote against Democrat Hillary Clinton that November, “if you deduct millions of people who voted illegally.” Beyond his false assertions about the 2020 election being stolen, he alleged widespread fraud in the 2024 election, despite winning all crucial swing states.
Russell Muirhead, a Dartmouth College professor who has studied Trump’s chaotic leadership approach, said the president has practiced long enough “to live in a world where you make your own reality” with no actual world “outside your own mind.”
Even Trump’s golf playing involves accumulating victories — at least at his own courses.
Trump claims 38 victories at golf clubs he owns. This includes a 2018 tournament in West Palm Beach, Florida, where he didn’t participate but defeated the winner in a later match, one where he missed the opening round, and another where he posted a final-round 67 — a score that would impress even professional golfers.
Matthews said during her White House tenure, she couldn’t remember Trump ever admitting error, even privately.
“When it’s obvious that it looks like a loss on paper, you have to kind of spin this somehow into a victory,” she explained. “Because that’s what Trump would want.”
