Timothy L. O'Brien is a senior columnist for Bloomberg Opinion. Read more opinion SHARE THIS ARTICLE Share Tweet Post Email

Photographer: Alex Wong/Getty Images North America Photographer: Alex Wong/Getty Images North America

Hanging on a wall behind the omelet bar at President Donald Trump’s golf club in West Palm Beach, Florida — where the commander in chief apparently stopped for a bite on Saturday after declaring a national emergency the day before — is an old, framed poster. It’s from an ad campaign Walgreens once ran featuring the president back when he was the sorcerer of “The Apprentice.”

In white block letters on the poster, next to a photo of Trump cocking his index finger at the camera and shouting in full “You’re fired!” mode, is a question: “CAN YOU WALK THE WALK?”

It’s likely that versions of this query still run through the president’s mind — and that he often finds himself coming up short, despite his public bravado and the loopy, ill-informed self-assurance he displays during pivotal moments such as his national emergency speech in the Rose Garden. That explains why he constantly spins his narratives toward success even in the face of obvious failures. To admit defeat is to admit he’s not walking the walk.

To that end, the White House released a document on Friday titled “President Donald Trump’s Border Security Victory” a day after Congress passed a spending bill that didn’t fund the border wall Trump demanded. The memo described the bill as a “legislative win” for Trump and outlined his intention to take executive action (and end-run Congress and the Constitution) by raising funds for the wall unilaterally.

It was inevitable that Trump would refuse to be stymied by Congress, and that he would take a victory lap regardless of what happened in the real world. In that context, his border-wall machinations are only partially about appeasing conservative pundits or his political base; for the most part, they’re about appeasing his sense of himself. He’s been doing this sort of thing his entire life: Spinning victory yarns from incontrovertible losses was a hallmark of his troubled business career.

Back in the early 2000s, his casino company, Trump Hotels & Casino Resorts, was in familiar territory: mismanaged, saddled with debt it had trouble repaying, and ultimately forced into bankruptcy. The enterprise had to be restructured, and Trump saw his stake in the company reduced. “I don’t think it’s a failure; it’s a success,” he told the Associated Press after his casinos filed for bankruptcy protection in late 2004. “It’s really just a technical thing.”

None of that amounted to failure, he also assured me at the time, because he still had a (much smaller) ownership stake after the bankruptcy. “It’s a successful deal,” he told me. “You’ll never write that, but it’s a great deal.”

"The only thing bad about it is I get some unsophisticated press that says, ‘Trump went into bankruptcy,’” he added. “Somehow the B-word [bankruptcy] never caught on very well in this country. But the smartest people in the country call me and say, ‘How the [expletive] did you pull that off?’”

Warren Buffett, who actually is one of the smartest people in the country, made fun of Trump’s business failures during a film and a live skit he performed in at Berkshire Hathaway’s annual meeting in 2005. An actor played a sobbing Trump, distraught over bad headlines about his bankruptcy, and he was gently consoled on stage by a sympathetic Buffett — until Buffett realized that someone as self-made and successful as he is actually has nothing in common with Trump, and the skit ended.

Trump told me he wasn’t insulted by Buffett’s satire: “It’s kind of an honor to be included in one of his movies.” He also told me that he didn’t think that Buffett’s vast wealth and investment prowess made him any more successful than him. “Yeah, well, he’s running a public company and he’s, like, a hundred years old,” Trump explained. “You know, I’m a [expletive] smart guy.”

This kind of stuff can be found even further back. In 1983, Trump bought into the nascent United States Football League. Although the USFL was trying to avoid a head-on confrontation with the National Football League by playing in the spring and was trying to keep a cap on salaries to keep its budgets reasonable, Trump pushed the league into fall play, began tossing out lavish salaries, and spearheaded an unsuccessful antitrust lawsuit against the NFL. The USFL, and Trump’s franchise, the New Jersey Generals, collapsed in 1986.

“The USFL wasn’t a big deal,” Trump told me several years after his football franchise cratered. “It was a small deal. I didn’t lose.”

Trump blamed his fellow USFL owners for the debacle rather than acknowledging any of his own missteps, in much the same way he has blamed others in the GOP for his lack of border wall funding. He also was indifferent (then as now) to the impact his fumbling had on those around him.

“None of it ever seemed to matter to Trump. It was just a little investment that didn’t work out too well, so he moved on to the next thing,” said Mike Tollin, who made a documentary about the USFL, in an interview with the Washington Post. “Didn’t matter that hundreds of people lost hundreds of jobs, from the peanut vendors to ticket takers on up.”

In a similar fiasco, Trump overpaid for the Eastern Air Lines Shuttle in 1989, using borrowed money and bringing no previous experience running an airline to the deal. He rechristened it the Trump Shuttle and then proceeded to make a number of operational errors, including installing gold-plated fixtures and other private-jet features that made little sense for a no-frills airline. Trump lied in one of his books, 1990’s “Trump: Surviving at the Top,” that the Shuttle under his management was profitable. “I’m glad I saved it. I’m proud of the way it’s been improved. It is now the best,” he also wrote

The Trump Shuttle went bankrupt in 1992.

“I got out at a good time. I walked away saying, ‘I’m smart,’” Trump later told the Boston Globe of his ill-fated Shuttle venture. “It was a great experience. I enjoyed it.”

And then there was Television City, a major Manhattan project that Trump torpedoed because he was mired in debt and couldn’t effectively negotiate with local residents and city officials. “I’ll sit back and wait until things get bad in the city, until construction stops and interest rates go up,” Trump bragged to the Chicago Tribune in 1989 about his standoff with local officials, foreshadowing the certitude he would later project about his border wall. “And then I’ll build it. But I will build it.”

Because Trump was unable to develop Television City or pay the property’s debt back, his banks forced him to sell it in 1994. He wound up with a lucrative stake in property someone else controlled, but he missed out on becoming a truly major New York developer.

“That was one of the great deals that I made,” Trump told Maine’s Press Herald in 2016 in an interview about Television City. “One of the best real estate deals.”

Trump brought this same brio to his presidential run. “If I’m president, there won’t be stupid deals anymore,” he said during one of the Republican debates in early 2016. “We will win on everything we do.”

You only really succeed at things by working hard and focusing on details, however, and as the Wall Street Journal’s Michael Bender noted Friday in a meticulously reported account, Trump and his team neither prioritized building a border wall nor assigned someone to be the White House’s point person on the project for most of the president’s first two years in office. Bender’s reporting pulls the legs out from one section of the White House victory proclamation issued Friday, which noted that Trump “was elected partly on his promise to secure the Southern Border with a barrier and, since his first day in office, he has been following through on that promise.”

It was only after Trump recognized in January that he was being consumed by a government shutdown he set in motion — and that he had been politically emasculated by a woman to his left (House Speaker Nancy Pelosi) and to his right (pundit and firebrand Ann Coulter) — that he fully embraced a border wall as his last stand. Now that he’s declared in a Rose Garden speech that building such a thing actually might not be due to an emergency (“I didn’t need to do this, but I’d rather do it much faster,” he said) but that he’s wiser in the ways of the world (“I never did politics before, now I do politics,” he said), what can we expect next?

Trump is cornered and outmaneuvered, so we’re likely to get more of the same as he continues to test the Constitution and the boundaries of presidential authority: constant spinning about winning, even when the losses are apparent.

This column does not necessarily reflect the opinion of the editorial board or Bloomberg LP and its owners.