WASHINGTON (AP) — In the January 2004 pilot of “The Apprentice,” Donald Trump said something he would never admit now.
“It wasn’t always so easy,” he said in a voice-over, noting that by the late 1980s, “I was seriously in trouble” and “billions of dollars in debt.”
It is one of the few times Trump has ever publicly acknowledged failure. Even then, he was reading a script meant to promote an against-the-odds credentials for viewers — previewing the combative charisma that propelled a political career a decade later.
In his telling now, Trump never loses.
Even when he clearly has been defeated — as he was in the 2020 election — Trump declares victory so often that his supporters believe him. He knows the power of repetition.
“The world for him is divided into winners and losers. And he’s always a winner,” said John Bolton, who was one of Trump’s national security advisers during his first term.
The Supreme Court strikes down his signature tariffs? Trump vows to work around the court, ensuring import taxes can be “used in a much more powerful and obnoxious way.”
His Justice Department stops appealing court rulings blocking executive orders aimed at punishing big law firms, then reverses course and renews those legal fights after coverage of the non-appeals looks like an admission of defeat.
One of the president’s sons, Eric, said his father “has never needed to project a ‘winning image.’ He IS the definition of a winner, based on what he has built and accomplished.”
But for the Republican president, the stakes for winning have never been greater than the war with Iran where he declared victory within days. He has repeated that assertion constantly even as Tehran continued to strike U.S. and allied targets and choke off the Strait of Hormuz, spreading economic pain around the globe.
With a ceasefire now in place, Trump is saying the United States has accomplished its goals. But reality does not substantiate that.
“Whether or not things are going well, that’s not going to detour him from declaring victory. That’s baked in the cake,” Bolton said.
’That was the messaging strategy’
Sarah Matthews, a former first-term Trump White House deputy press secretary who resigned when a mob of Trump supporters rioted at the Capitol on Jan. 6, 2021, said the president’s “ego won’t allow him to acknowledge defeat.”
“That was the messaging strategy,” Matthews said of her time at the White House. “It was, ‘How can we redefine this loss as a victory?’”
Current White House spokesman Davis Ingle countered that Trump “proudly projects the unmatched greatness of our country consistently in his public comments.”
Trump’s framing of setbacks as wins can be traced to his early days as a real estate developer. In 1973, federal authorities sued Trump and his father, alleging racial discrimination in renting apartments their company built in Brooklyn and Queens, two New York City boroughs.
The Trumps were urged to countersue by Roy Cohn, the notorious attorney who rose to fame as an aggressive promoter of Sen. Joseph McCarthy’s “red scare” hearings of the 1950s.
The case was settled after both sides signed an agreement two years later, prohibiting the Trumps from “discriminating against any person.” Trump declared victory, noting that there had been no admission of guilt, despite the Justice Department calling the settlement “one of the most far-reaching ever negotiated.”
David Cay Johnston, author of “The Making of Donald Trump,” said Cohn “taught Donald, you never concede as much as a comma.”
“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 said.
Bankruptcies didn’t dent Trump’s image
Through the years, Trump consistently lost money in his business ventures, launching failed lines of namesake products that included steaks, bottled water, vodka, a magazine, an airline, a home mortgage concern and online classes known at Trump University.
Barbara Res, who worked for the future president for nearly two decades, remembers him pitting top executives against one another to ensure he remained his company’s most powerful voice, even as losses mounted.
Those experiences informed today’s Trump, she said, where “nothing is wrong to him, if it helps him.”
Robert Thompson, a Syracuse University professor of television and popular culture, said the success of “The Apprentice” was built on earlier factors. Those included the hubris built into the title of Trump’s 1987 book, “The Art of the Deal,” as well as his aggressive courting of media attention and obsession with naming buildings after himself.
“When you need someone to quickly and efficiently represent ‘American Rich Guy,’ Trump has kind of cast himself in that position and everybody goes along with it,” said Thompson, who added, that, once that occurred, “the actual ups and down of his portfolio doesn’t matter that much.”
After his three casinos in Atlantic City, New Jersey, failed, Trump insisted to The Associated Press in 2016 that “Atlantic City was a great period for me.”
’You make your own reality’
After he lost the 2016 Republican Iowa caucus, Trump posted that Texas Sen. Ted Cruz “illegally stole it.” Trump went on to win the presidency but lose the popular vote to Democrat Hillary Clinton that November, and said he had actually captured that, too, “if you deduct millions of people who voted illegally.”
Russell Muirhead, a professor at Dartmouth College who has written about Trump’s chaotic governing style, said Trump has been at the practice long enough “to live in a world where you make your own reality.”
Even the way Trump plays golf means racking up wins — at least at his own properties, where he boasts of many club championships and no second-place finishes.
Trump says he has won 38 times at his golf clubs. That includes a 2018 tournament in West Palm Beach, Florida, where he did not play and only claimed victory after topping the winner in a subsequent match. Trump also claimed the same course’s senior championship in 2023, despite missing the event’s first round, instead listing a score shot on the same course earlier.
Johnston said Trump “has this fictional narrative in his head” and is “like a screenwriter. When you need to change the narrative, you just change it.”
___
EDITOR’S NOTE: Will Weissert has covered politics for The Associated Press since 2011 and the White House since 2022.
Copyright © 2026 The Associated Press. All rights reserved. This material may not be published, broadcast, written or redistributed.
