News & Politics

Trump vs. Oprah: The Matchup We Deserve?

Barack Obama, Oprah Winfrey

Back in May 2011, President Barack Obama devoted a good chunk of his White House Correspondents’ Dinner speech to roasting an unsmiling Donald Trump about the whole “birth certificate” thing.* Obama bashed the guy, right to his face, over and over. Take a look:

And all of Obama’s minions and acolytes rejoiced. Another glorious success for President Lightbringer! #YAAAAAS #KWEEN #SLAYYYYYYYY

Five and a half years later, Trump was elected the 45th President of the United States. And I have to wonder: Would he have decided to run at all if the most powerful man in the world hadn’t publicly humiliated him like that? Would he have been so driven to prove everyone wrong? Would he have so desperately craved such sweet, sweet revenge?

Obama made a big mistake that night. Previous presidents had used the WHCD as a platform for folksy self-deprecation, but that wasn’t Obama’s style. His overweening pride and thin-skinned narcissism got the better of him, and he abused his power over one of his own constituents for petty personal reasons. He used the WCHD as just another bludgeon to smash his domestic enemies over the head. And in this case, it blew up in his face spectacularly. Just a few years later, Obama had to grit his teeth and hand over the reins of power to the guy he had taken such pleasure in mocking before the whole world. He thought he’d left Trump in the dust, but nnnnnnnope.

Obama gave us Trump. That’s his legacy.

But did Trump learn anything from the whole experience? Does he understand that using the bully pulpit to bully his critics can backfire?

Of course not.

What’s he so angry about? This:

I don’t know why Oprah is on 60 Minutes either, but I thought it was a heartening story. It showed that people of wildly varying political beliefs can still get along, and maybe even become friends. It reminded viewers that a person is an individual, not just a series of checkboxes (white☐ Christian☐ Trump voter☐). I don’t agree 100 percent with anybody at that table, but they’re all human beings. They’re not just straw men to beat up. No, not even Oprah!

That’s not what Trump saw, though. Trump is all about Trump. He can only gauge people and events in the outside world by their effect on his own ego. In that way, he’s much like his predecessor. I didn’t like it between 2009-2016, and I don’t like it now. I didn’t like Obama’s stupid speeches, and I don’t like Trump’s stupid tweets. But a lot of Republicans are glad to finally have their own Obama, so that’s nice for them.

Many, many liberals begged the GOP to nominate Trump, for the same reason I begged them not to nominate Trump. We both thought he didn’t have a chance of winning, and we both were wrong.

Oprah has repeatedly insisted she won’t run for president. It’s not in her DNA, she says. Which, in politics, is a solid Maybe. If she runs, I don’t think she can win. But then, that’s what I said about the last upstart.

If she ends up deciding her DNA is up to the challenge after all, if she decides to prove Trump wrong, she’s already got a 2020 cheering section. Like this guy:

As a wise man once said: “So you’re tellin’ me there’s a chance!”

*No, Obama was not born in Kenya. When he made that claim, he was lying.