'We’re not even close to how bad it’s going to get': Why Trump will never, ever admit he's failing
Donald Trump makes a pointing gesture toward the media during a speech to a large crowd at a Thank You tour rally held at the Giant Center (Shutterstock)

President Donald Trump's first 100 days are -- by any measurable standards -- looking an awful lot like a failure to many observers, but Trump himself insists that everything is running perfectly.

According to a feature in Politico magazine on Sunday, Trump's constant insistence that everything is great -- even in the face of bankruptcies, closings and collapsed ventures -- is a key to his success and always has been.

"How, wonder people who are even fleetingly familiar with presidential history, can Trump look back at the past three months and seriously say they were the best ever?" asked Politico's Michael Kruse. "To others, though, who have worked with him, have been watching him for decades and know him well, nothing could be more familiar."

“I just shake my head,” one former Trump casino executive told Kruse, “and I say, ‘Well, that’s Donald Trump.’”

Kruse compiled a record of the many, many times the president -- when faced with business closings, the collapse of his airline, his steak brand, his bottled water brand, his sports team ownership and on and on -- has simply said, "Things are great. Business is great" and somehow gotten away with it.

These statements, Kruse wrote, "are potent shots of unadulterated, time-tested Trump --

short, confident declarations of success, in spite of objective evidence of failure, uttered with total disregard for the parsing and fact-checking that constitutes so much of the coverage of him and his administration. Biographers, ex-employees, veteran New York City gossip columnists, public relations professionals and political operatives from both major parties say recognizing this well-established pattern of behavior—stumble, proclaim victory, move on—is imperative to understanding Trump."

Trump never feels like he's failing as long as his bottomless need for attention is being met. Furthermore, the president "has perfected a narrative style in which he doesn’t merely obscure reality -- he tries to change it with pronouncements that act like blaring, garish roadside billboards... (H)e has defined himself as a success no matter what -- by talking the loudest and the longest, and by insisting on having the first word and also the last."

The approach has worked at every turn thus far in Trump's adult life, Politico said. Many people who are familiar with Trump and have watched him in the long term say that he may well pull it off, powering through his actual failures and missteps with a relentless barrage of PR.

“He creates his own reality,” former Trump Organization vice president Barbara Res said. “He created the reality that he was this big, successful businessman, and now he’s creating the reality that he’s a big, accomplished president.”

Republican strategist Rick Wilson, one of Trump's fiercest critics, said, "He’s gotten away with this game his whole life."

“We’re not even close to how bad it’s going to get,” Wilson said. “It’s going to get substantially more difficult to keep selling this crap. He’s not dealing with some random vendors in New Jersey. He’s dealing with the American people. But I will say this: His cult has shown a great willingness to be a cult.”

Jack O’Donnell -- the former casino executive -- told Kruse that Trump will use the approach for as long as it works.

“If you or I were sitting there,” he said, “we would have trouble staring into the camera and lying. He doesn’t.”