Donald Trump, loser: He now has to own the insult he most loves to hurl at others

Donald Trump appalling character and personality — impulsive, combative, dishonest, narcissistic — are so darkly powerful that even four years in the White House had little visible effect. Where others have been humbled and inspired, he felt only affirmation for his view that life is a vicious battle and that all that matters in the end is that he escapes the label he dreads the most: loser.

“Loser” is the insult Trump has hurled at so many people and institutions that his obsession with the word, and the status it confers, is obvious. This lifelong fixation explains, in large measure, his to-the-death struggle against vote counts that turn against him and his tendency to attach the loser label to everyone and everything he dislikes.

Before he ran for president, Trump filled his loser hall-of-infamy with roughly equal numbers of businesspeople, entertainment figures, politicians and journalists. The main thing that bound them together was that they either denied Trump something he wanted or challenged the “I’m-a-beloved-winner” fantasy he spun about himself.

U.S. President Donald Trump speaks in the briefing room at the White House on November 5, 2020 in Washington, DC.
U.S. President Donald Trump speaks in the briefing room at the White House on November 5, 2020 in Washington, DC. (Chip Somodevilla/Getty Images)

Rosie O’Donnell, comic, actor and talk show host, was peppered with Trump’s loser tag after she dared to speak the central truth about Trump, that he’s not the great businessman he claims to be on national television.

“He’s been bankrupt so many times!” said O’Donnell on “The View” way back in 2006. “The people that he owed money to got shorted out, but he got to try again and again.”

O’Donnell also challenged the Trump claim that he had gotten little help from his immensely wealthy father, and she named the game he has played with regard to his own success story. “He’s a snake oil salesman,” said O’Donnell, referring to Trump’s lifelong effort to sell himself as one of America’s great winners.

As she spoke, O’Donnell was one of few Americans who publicly challenged the Trump myth which he had created on the foundation of privately held business organizations that almost never released reliable documentation of their profits, losses, assets and liabilities. One of the few who joined her was journalist Tim O’Brien, who punctured Trump’s claims in a scathing book called “Trump Nation.” Trump branded O’Brien a “loser” too, and also sued him in federal court.

Donald Trump vs. Timothy O’Brien marked one of the few times in Trump’s life that he dared to enter an arena where mere talk is not enough to prevail. The trial produced a defeat for Trump — in other words, he was the loser — and substantial evidence that O’Donnell had been correct. These facts didn’t deter Trump from attacking others as losers.

Trump then focused his loser laser on those less able to fight back with facts. He picked on showbiz folks including actor Richard Belzer, producer Danny Zuker, comedian Russell Brand, comic Bill Maher, Cher and Howard Stern, labeling all of them losers. During this time, Trump also began going after entire media organizations, including the New York Daily News, Huffington Post, Politico, Deadspin and New Hampshire’s Union Leader.

Only those with real knowledge of the media landscape would understand why Trump felt compelled to go after websites and newspapers. When he targeted a bunch of political types, he ran into the same issue. Did the general public really care that he thought consultants like Karl Rove, Frank Luntz and Ana Navarro were losers?

Turns out, Trump’s turn toward these supposed enemies came in 2013, as he began to consider running for president. These “loser” bombardments were, it now seems, a way for Trump to damage and discredit certain critics before his run began.

In office, Trump couldn’t resist using the loser epithet even when it was certain to backfire. When The Atlantic reported that he had called America’s war dead “suckers” and “losers,” the president was revealed to a meanspirited child. In fact, his use of the word loser might be traced to his upbringing in a family where his father demanded constant winning and the mentorship of a childhood coach who posted on the locker room wall, Vince Lombardi’s motto: “Winning isn’t everything, it’s the only thing.”

In 2018, Trump made it clear that he thinks winning is required of him by the entire nation. “We love winners,” he famously observed. “We love winners. Winners are winners.”

As he joins the small club of presidents who tried and failed to win reelection, Trump is a loser at the greatest contest he ever waged. This time, he is unable to keep the numbers secret, which he did as a private businessman, and he won’t benefit from the strange workings of the Electoral College, which let him prevail in 2016 as he lost the popular vote count by 3 million.

Trump’s loser status will be written in the history books. He is, officially, the thing he dreaded most.

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