How Donald Trump felt 20 years ago
He says he feels better than he did then, even with Covid. But even if that's true (which it probably isn't), maybe that's not saying very much. A Backbencher investigation.

President Donald Trump today tweeted "I feel better than I did 20 years ago!” Even though he has Covid and is spreading it like so much confetti across the United States, he feels better at 74 than he did at 54.
What was Trump doing 20 years ago? In those days, only two newspapers in America were interested enough in Donald Trump to cover him regularly: The New York Daily News and the New York Post.
The Daily News reported exactly 20 years ago today, on Oct. 5, 2000, that Trump was paying a $250,000 fine to NY state for secretly lobbying against a Native American tribe that wanted to open a casino in the Catskills (a threat to Trump's Taj Mahal). Till then the highest fine ever imposed by NY state lobby regulators was $75,000. Roger Stone lurked in the background of this characteristically tawdry episode.
The New York Post reported on Oct. 5, 2000, under the headline “Payback Time For Trump?” that the Donald was dealing with his former top casinos guy Nick Ribis taking over Resorts International next door to the Taj. There was the usual dispute about whether Ribis got fired or quit. Today Ribis is still running RI and RI's hotel is still there. The Taj went bust some time ago. It's now a Hard Rock International property.
Both tabloid news stories strongly suggest that Trump wasn't feeling all that great on Oct. 5, 2000. "The Apprentice," which revived his business a little and paved his way to the presidency, didn't premiere until four years later.

Trump had planned to run for president in 2000 on Ross Perot’s Reform Party ticket, but he didn’t get the nomination; he lost it to Pat Buchanan, whom he called a “Hitler Lover.” Trump had left the Republican party because it was (his words) “too crazy right.” A few months later he’d register as a Democrat.
Trump’s 26 year-old girlfriend Melania, wearing a red bikini, posed suggestively in 2000 across the presidential seal for Tina Brown’s Talk magazine, which clearly thought the idea of Donald Trump wanting to be president was too deliciously idiotic not to write up. (For more on Trump’s 2000 presidential campaign, I recommend this droll remembrance in the Guardian.)

Perhaps when Trump says he feels better than he did in 2000 he means that he felt bad in 2000 because he couldn’t win a presidential nomination even from the mickey-mouse Reform Party, and what press coverage he received for it contained a strong undertone of mockery. Today Trump is able to win a presidential nomination, twice, from the Republican Party, and even to become president. That’s definitely an improvement. Don’t even try to explain this to your 20-years-younger self, because that person won’t believe you.
Or maybe Trump says he feels better because in 2000 his politics were to the left of Joe Biden, and being a conservative better suits his temperament. Trump was in those days in favor of a one-time wealth tax of 14.25 percent on fortunes that exceeded $10 million. It was, Stone told the Los Angeles Times, “something he feels strongly about.” Trump also favored single-payer health care and, as a transitional strategy, a policy involving “health marts” that resembled Obamacare. I wrote about all this four years ago for Politico. Trump, or at least his ghostwriter David Shiflett, wrote it up in Trump’s 2000 book The America We Deserve. It never seems to come up when Trump rages against taxes or socialized medicine or Obamacare.
Or maybe when Trump says he feels better than he did 20 years ago he doesn’t mean that any more than he means many of the other things he says. Maybe he’s just trying to persuade people that he feels really great, which is pretty unlikely, actually, because he’s caught a deadly virus less than a month before Election Day, and the election wasn’t looking that great for him even before that happened, and he’s really sick, and he’s trying to pretend he isn’t really sick, and nobody believes him, and he knows that, too, because he’s been watching even more television lately than usual, and now he’s gone and checked himself out of Walter Reed.
Maybe that’s what’s going on.