Andrew Sullivan is one of America’s best known political observers and writers. He is an independent-minded conservative who supported Obama, was a leader of the gay marriage movement, and has since argued forcefully against Donald Trump. His Substack is one of the most popular in the world. He recently did that rare thing among public intellectuals and revisited his earlier opinions about the former president. I wanted to know: which ones does he now think were wrong?


Andrew Sullivan: When I went back and looked at that big essay I wrote in 2016, I asked myself: what were the things I was specifically worried he would do, and did he actually did those things? To me the most promises that he made in 2016 were authoritarian in nature: the pledges to round up and deport 11 million unauthorised immigrants, to ban all Muslim immigrants from the United States. He threatened his opponents with either killing them or prosecuting them, including Hillary Clinton. And of course, he was also a huge enthusiast for war crimes. He loves torture. He’s a depraved human being. But nonetheless, all those things he didn’t do. Did he violate a supreme court order? No. Did he exceed his authority? Yes — he did send the military down to the border with funding that wasn’t allocated by Congress. But that is not exactly the kind of terrifying thing that one feared back in 2016. 

FS: So the authoritarian rhetoric didn’t materialise. Do you think that’s because it was always just talk, part of a tough guy image? Or do you think he just wasn’t capable of executing it?

AS: I don’t think he actually likes the exercise of power. He’s not that interested in controlling the lives of everyone around him, or indeed most Americans. He’s concerned primarily with his own ego, with his own glory, and with his own sense of being right in a particular moment. And so when it comes to difficult things, like rounding up 11 million people, he didn’t even try. There was some increased enforcement from ICE, but not much. We know how much wall he built, which is about a few hundred feet; we know how much Mexico paid for it, which was zero.

The worry was that he could declare a state of emergency when faced with a crisis, assume all sorts of powers and run the country like a dictator. Well, there were two moments when that was possible. The first was when Covid happened — in fact, his instincts were not to assume all the powers, and in fact, he did rather conventional things. Then, after the Floyd riots in 2020, half the country’s cities went up in flames, but did he take the opportunity to send tanks into the streets? No — if anything the police were under-enforcing the law in that period and there was mayhem. So all the great fears and panics about him seizing total power turned out to be overblown. And I think it’s worth saying that.

FS: Some people have accused you of “Trump derangement syndrome” for the level of your concern. In retrospect, do you feel like you had a mild case of it?

AS: No. The former President Donald Trump is himself deranged, that is where the source of the derangement is. All we’re doing is responding to what he says and what he does. And what he said was: I intend to upend the entire Constitution of the United States and run it as a dictator. He didn’t do it. Now, the question is, why didn’t he do it? And some people say, well, he was checked by others. And he was. But my sense is he doesn’t actually want that kind of control. It’s too much responsibility.

FS: It’s an incredibly important point that, isn’t it? That, contrary to those fears, there is something intrinsic to Donald Trump that is un-serious, or even, as you wrote recently, almost comic.

AS: It’s always been hard to wrap your head around him because on the one hand he’s talking like Mussolini; on the other hand he’s talking like a cable news host. And you’re not quite sure whether he’s commenting on the news or aiming to be a dictator. But there is one element in which he is dangerous, very dangerous to a constitutional republic, which is that he really doesn’t believe that law applies to him.

In fact, he has recently been calling for total immunity for the President for everything he does in office, including murdering political opponents. That’s his public position, that he wants total immunity. Whenever he has been caught out personally, whenever he has been investigated personally, he has responded unconstitutionally: he attempted to obstruct justice, he attempted to get rid of various attorneys general. He clearly tried to rig the election by using foreign policy to get Biden in trouble with Ukraine. Of course, the ultimate example is January 6th, where he sits there and allows the Capitol of the United States to be ransacked and a riot to take place in order to slow and defer the certification of the election.

FS: We actually spoke two days after January 6th, on January 8 2021. And I remember very clearly at the time that you were very exercised by it. I was making the case that maybe it was more performative, or maybe it wasn’t a full attempt at revolution. And you were saying: don’t downplay this, Freddie, don’t make light of it. Do you now, in retrospect, feel that January 6th was as Republic-ending as it seemed at the time?

AS: Well, it didn’t end the Republic did it? That’s the main conclusion we have. All this was an attempt, not to seize power, but to appease his ego. He didn’t have links in the military to allow a coup to take place; he had no support in the Senate or the House to initiate some kind of coup. It was, in the end, kind of an empty gesture. But what it showed was that he was prepared to take the Republic to the very edge of the cliff, dangling over it, and then, according to his whim, whip it back to safety — or not. And that is an unacceptable level of risk for any society to tolerate. 

FS: The critique that you’re now making is basically that he’s fundamentally unserious, and craven in his own self-defence to the point where no rules are worth obeying if he can cheat them to get out of a sticky situation. Those traits aren’t unique to him as a politician. But the rhetoric that has come from the Democrats ever since 2016 — and still from Biden — is that he is an existential threat to the Republic, he’s a fascist, he’s a source of incredible danger. It’s a huge shift if we no longer think that that’s a risk.

AS: But we do think it’s a risk, for the following reason. The entire constitution of the United States is based upon the rule of law. The rule of law has to be applied and be seen to be applied, as far as possible, equally. He has openly stated that the President should be above and outside the law. If he is convicted of crimes, some of which are quite serious with respect to his political position, he doesn’t care. He will seek to be re-elected to overturn the rule of law with respect to himself. In other words, we will have an election in which he will say: it’s me, or it’s the rule of law.

FS: So is that is your biggest fear looking forward? That some kind of constitutional break might happen either at the end of his time in office, if he wants to stay longer or something along those lines?

AS: Yes. He has never accepted the result of an election he didn’t like, whether it was his own, or anybody else’s: you can go through the record. He just doesn’t believe that he needs to play by the rules. And he believes that if he loses, it’s because it’s rigged. Now, when a President stands up and says, “The entire system is rigged, you shouldn’t trust it, you should only trust me,” are you really saying it’s a responsible thing to support that person? When he’s already shown that he is indifferent to a peaceful transfer of power? Once already he has tried to stop himself being removed from office. He’s told us in advance that he won’t even recognise the results of this coming election if he loses. So we’re headed for a constitutional crisis if he doesn’t win outright, clearly.

FS: We’re possibly headed for a constitutional crisis if he does win also. You may get all sorts of constitutional tinkering being proposed by governors of states who reject a President Trump. We might start seeing the reverse of what we’re now seeing in Texas — blue states defying the President. There’ll be people on the streets if Trump is re-elected, surely?

AS: Yes, I think that there will be. And he has already said that he’s prepared to invoke the Insurrection Act if such violence takes place. Of course, he won’t be able to in November because he won’t be president till January. So martial law will have to wait. But nonetheless, it’s a slightly alarming prospect. And the fact that we’re at a point where both sides are beginning to say they don’t trust this election at all, and will inflict violence or demonstrate against it afterwards, just shows you the lengths to which we’ve gone. I think it is simply not fair to blame others for this. Others do bear some of the blame, but the chief driver in the delegitimisation of the American constitutional order is Donald J. Trump, because he cannot bear a system that might in any way at any point overrule his own wishes and his own interests.

FS: Let’s posit that he wins anyway. What do you think would happen policy-wise? Everyone here in Europe is discussing the risk of isolationism: the sense that if Trump wins, Nato is imperiled and support for Ukraine will either just stop abruptly or gradually fade away, and Europe will pretty much have to fend for itself. Do you think that’s true?

AS: I do, pretty much. Not just because he feels that way, but because a large majority of his own party believes that too (at least the base of the party, not the elites that are still part of the 20th-century architecture of international law). No, I think if he’s elected, then Ukraine will be partitioned. And I think at some point, Taiwan will be given over to China. And I think a large number of Americans will regard that as a pretty sensible, sane way of moving forward in the world.

FS: And would you be one of that large number of Americans?

AS: I’d be pretty close to them, yes. I don’t think there is a desire in the United States, nor has there really been for the last 20 years, for long engagement in conflicts far away. The people whose kids go to fight those wars don’t want their kids to go fight those wars. And a lot of people just simply look at the state of the US-Mexico border and say: why are we spending billions of dollars on the border between the Russian-dominated provinces in Ukraine and the rest of it? Why, when we can’t do it for our own border? That’s an incredibly potent argument.

FS: The world order is certainly going through a seismic shift, one that may involve war or will conflict being evaded and a deal being struck. The argument of those who support Trump would be that he’s not so deeply ideological, he likes a deal and, as you say, he’s not seriously attached to a particular set of principles. And they say: that’s the kind of leader we need right now to smooth things over. 

AS: Yes. There are plenty of reasons, policy-wise, why I’d be happier with a Trump administration than a Biden one. There’s immigration, which I think the Democrats have completely screwed up. The numbers of people coming over are extraordinary at this point. And I think if he got a majority in the House and the Senate, he could easily pass immigration reform, and this time, unlike in 2016, he won’t be bamboozled by people like Paul Ryan into thinking that the most important thing is a tax cut for the super-wealthy.

I also think that regarding the wokeness stuff, even though I really find Trump horrid on so many levels, if he’s the only thing that can stop this stuff from being imposed across the country and across the United States Government, then you can see why I might prefer him over Biden, who is giving in to woke at every level. The federal government is involved in systematic DEI: in all of its capacities it now has putting equity at the heart of everything as a policy. He would remove that and there would be support for ending DEI in corporate America and in universities. He’s clearly taken out a position — even if he’s not interested in that stuff, he’ll find someone who is. And that’s a huge thing for the base. It would happen, I think.

FS: And meanwhile, he’s not homophobic especially is he?

AS: I don’t think there’s much evidence that he’s anti-gay. I don’t think any of the core civil rights that we’ve won — the right to marry, the right to be in the military — are in any way in doubt. What is in doubt is whether we should fast-track children for sexual transition, which is a hugely controversial and difficult issue. And I think he might help put the brakes on that.

FS: By your account, it’s sounding pretty good so far! What’s not to like about Trump II?

AS: The end of the rule of law and the end of the American Constitution, which are far, far more important.

FS: What about the Left? Just as you are evolving and looking again at some of his traits, do you think the Left will learn from the mistakes of 2016-2020, when they only exacerbated the polarisation by completely freaking out about Trump’s victory?

AS: No, they’ll go absolutely bonkers. But let’s talk about which elements. The upper-middle class white people will go bonkers. But what’s fascinating is that on the policy measures, African Americans, Latinos, Asians, even some gays, are moving in the direction of Trump in ways that could be truly devastating. It is perfectly possible Trump will win in a landslide. I think that’s more likely than any other actual scenario.

But what the Biden people say is that when push comes to shove, the idea of four more years of that kind of chaos is all the argument that they need. Just don’t vote for chaos. Stay where you are. Things are actually improving: the economy has done better in the United States than anywhere else in the world over the last few years and we are making progress on climate. There’s all sorts of things they can say. But they have a doddering, ancient guy who can’t really command the public’s attention. You have the impact of inflation, you have the failure on immigration. I think it’s Trump’s for the taking, I really do. 

FS: It feels your heart and head are pointing in different directions. I asked about all the policy areas and you’re basically on board. But there’s this one principle, which you believe is most fundamental, which is that he doesn’t respect constitutional process. 

AS: But that is the core question. In our democracies, policies come and go. All sorts of things change. All sorts of governments get things wrong. But the constitutional process allows us to change government to sustain a pluralistic democracy, to have a system where everyone respects the rule of law. Those things are what ultimately matter in a society. 

FS: I’m going to leave it there because you’ve summed it up perfectly.

AS: Thank you for having me unspool all my conflicts in public. I do think it’s important for writers to do that occasionally. Because I don’t think my judgement was totally off, but I think it missed a few nuances, which you’ve now learned about. But I still cannot vote for Donald J. Trump.

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