Trump's Chances

On Election Day in 2016, Washington Post columnist, Henry Olsen, bravely took to Twitter with a bold proclamation: Trump could win! Four years later, Olsen is less bullish on Trump’s chances.

Earlier this week I had Washington Post columnist Henry Olsen on the podcast. During our conversation, Henry discusses why Trump has an uphill battle—and what would have to happen for Trump to pull off another miracle.

Click here to listen to our full conversation.

Here’s a lightly edited excerpt:

Matt: What do you make of the current state of the conservative movement and the Right—and I would include in that, you know, like Never Trumpers?

Henry: The Right needs to rethink and reform. It's needed that for decades. It tried to deny it. And Trump ran through that blindness to the nomination—and then to the presidency. If Trump is out of the picture, that need is still there, but there's still a willful blindness among many elements of the party. I think the first thing to understand is the conservative movement was always a minority of the Republican Party. That's something the conservative movement did not want to recognize. And it still doesn't want to recognize it. And within the conservative movement, the largest vote getting element of the conservative movement, is the people concerned about religious liberty and moral issues—not the ones concerned about economic issues. Another thing that people have tended to downplay is: what does conservatism mean in the modern age, and what does movement conservatism mean? With respect to Never Trumpers, Bill Kristol, has pretty much acknowledged, he's not coming back to the Republican Party. Others are in that similar boat. Others will try and come back— and they may have influence or leadership roles—but very few of them seem willing to seriously rethink them, which means that they'll basically be cast in what I call the ‘restorationist wing of the Republican Party’—people who want to [change] a couple of bells and whistles changes, but otherwise want to return to what they envision the state of the party was pre-Trump. And I think that is a politically losing gambit. And so consequently, that simply would prolong Democratic rule. 

Matt: Speaking of Republicans who could kind of carry the Trump mantle potentially. You recently went to New Hampshire to watch Kristi Noem, the Governor of South Dakota, at an event. Talk about that. 

Henry: Well, I would have liked to have watched her just that her swab Svengali, Corey Lewandowski, Trump's former campaign manager, kicked me out of the event that I had been admitted to, because he didn't want to see…let her be observed. Now, you know, take that for what you will, as I wrote. Usually, when your chief strategist doesn't want you to deliver a simple meet and greet stump speech, that's a problem. I think the way to think about the Trump legacy is there'll be people who are competing for different ways to interpret it. And you will try to see people who try and emulate that angry ‘drain the swamp’ mentality. I think part of his appeal, particularly towards the end, was that he was an unorthodox carrier of an orthodox message of Republicanism, and you'll see people like Mike Pence try to do that. Both of those wings I call the “Imperial Successors” and their basic mantra is “more Trump less tweets,” even if they disagree on what “more Trump” means. And then there are people who I label as the ‘young reformers’ who will be taking a more substantive look says, “look, what we will need to do is downplay the personal elements, and certainly excise any racially charged language, but up play the way in which he was trying to define nationalism in a way that redefines what it means to help people in the 21st century.” Those are people like Tom Cotton, or Marco Rubio and Josh Hawley. And when you're looking three years out, one thing I know, in American politics is that lots of the underlying factors tend to change slowly. But the who's, the people who co-opt the leadership of those factions change rapidly. You know, if you were asking me, in 2011, I could tell you that there was going to be a strong candidate, you know, trying to win the Tea Party base, and particularly after 2012. I would not have said Ted Cruz would have been that person. But over 2013 in the first half of 2014, he made himself into that person. So I think the who will find itself—

Matt: Ted Cruz wasn't even elected until 2012 to the U.S. Senate. Yeah, you would never have come up with him. 

Henry: That my point. We're talking here and on the eve of an election in 2020, about who's going to basically be national figures by the time of 2024. And there are some people who we can feel comfortable will be there. And there will surely be people we've never heard of. Just like you mentioned Kristi Noem. A year ago, nobody would have said Kristi Noem. But the fact is she's done an excellent job of profiling herself as a new type of an old, hard-right, conservative. And so, consequently, she's getting attention. There will surely be people like that. Much as Chris Christie got elected in 2009, and by 2011, was being begged by people to get in the race to stop Mitt Romney, because they thought he wasn't electable. And Christie was no-- 

Matt: Christie should have done it. As it turns out, he should have, he should have run for it, then. 

Henry: Yeah, well, you know, it's like I wrote in the conclusion of the Noem piece, Shakespeare says, “There is a tide in the affairs of men / Which, taken at the flood, leads on to fortune.” Now Christie should have said, “I'm not ready. But this is my chance” and get on the boat while we wanted him. And there's going to be people who do that. They'll feel they're not ready, and they'll pass their chance. And then there'll be people who will jump on and they've not ready, and they'll go farther than they should, but they'll sink anyway.

Matt: What do you think of this hunter Biden New York Post saying, Is this gonna have any legs or, or not?

Henry: Not unless something else comes out. Because we're just in such a state where if you're partisan on one side or another, you believe what you want to believe. You know, partisans on the Republican side, see this and say, “See, this proves to me what I already believed that Joe Biden's family is corrupt.” And Democrats look at it and say, “See, this is thinly sourced, it's Russian disinformation,” and so forth. There's very few people in the middle, who will look at it, and try and weigh it. And there's very few people who are the traditional gatekeepers who will actually try and weigh it fairly, because so much of the people who comment on these things are locked into those viewpoints. You know, we've seen so many of these things over the last five years of this outrageous allegation—much of them against Trump and his coterie of buddies—but some of them against Democrats and Biden. And I think the swing voter has just kind of like, checked out of that. You know, it's now just noise, unless there's some reason for it to break through and it has not reached that level of breaking through.

Click here to listen to our full conversation.