In March 2015, William Kristol put a photograph of a young and artfully scruffy Bob Dylan on the cover of The Weekly Standard — “the neocon Bible,” as the magazine he co-founded and edited was dubbed. The photo illustrated a cover story, provocatively headlined, “Bob Dylan, Traditionalist.” 

As a lonely wanderer in the political wilderness in these days of Trump and Trumpism, an iconic Dylan lyric may capture best Kristol’s no-direction-home predicament:

“How does it feel? To be without a home

Like a complete unknown, like a rolling stone.”

The son of “the godfather of neoconservatism,” and a traditionalist in his own right, Kristol has spent his career making the case for conservative policies and politicians. He spent the last five years trying to rally his fellow Republicans to support his “Never Trump” cause. 

It didn’t work. 

The longtime editor of the now-defunct Weekly Standard could not convince enough Republicans to oppose former President Donald Trump, who remains immensely popular among Republican voters nearly a year after losing his reelection bid. And many of Kristol’s fellow Never Trumpers have begun to return to supporting the party, seeing a more palatable opening to support Republican candidates again now that Trump is out of office.

Not Kristol. He raised eyebrows inside the Beltway last month when the McLean, Va., resident endorsed Democrat Terry McAuliffe in Virginia’s gubernatorial race. 

McAuliffe, a fellow McLean resident who served as governor from 2014-2018, is facing Republican Glenn Youngkin, a former CEO at The Carlyle Group who is viewed by some Republicans as a return to the party’s moderate roots. But Kristol isn’t swayed: “Youngkin fundamentally is unwilling to break with Trump and Trumpism,” he told Jewish Insider in a recent interview. 

Best known for his proud support for interventionism and the Iraq War, Kristol, who is now editor-at-large of The Bulwark, decided that it would be disingenuous not to weigh in on the heated governor’s race in his home state. Not to mention that the McAuliffe campaign asked for his support. “I just felt like once I got asked my opinion, it seemed a little ridiculous to say, ‘Well, I’m staying out of it,’” he explained. 

In conversation with JI, Kristol discussed whether he still identifies as a Republican (no, not really), what he makes of the growing contingent of Democrats who are hostile to Israel (“it’s very foolish to just write off the Democrats”) and whether Iraq was really worth it (“I’m uncertain about Iraq”). 

This interview has been edited and condensed for length and clarity.

Jewish Insider: I’m curious how you would define yourself politically these days. Would you call yourself a Democrat? Or was the endorsement of McAuliffe purely candidate-based?

William Kristol: Some of each, honestly. Virginia doesn’t have party registration, so I always use that as a way of avoiding the ‘What party are you now in’ question. But Pete Buttigieg said during the campaign that he hoped he would appeal to, and that he hoped Biden would appeal to if Biden was the nominee, what he called ‘future former Republicans.’ I’ve used that term a few times to describe myself now. As a friend pointed out, there’s only so long you can be a future former Republican. At some point, you have to decide, Are you a former Republican, or are you still? I guess I’m more on the former side. 

Even the mainstream Republicans are not willing to repudiate Trump and Trumpism. If the Republican Party were where [Rep.] Liz Cheney [R-WY] was, I would be in a different place. I would still disagree, and I’d probably still be more moderate, or liberal, if you want to compare me to someone like Liz Cheney or even [Rep.] Adam Kinzinger [R-IL]. As a party, no one would have criticized them for not seeing the threat earlier. But most of the Republican Party refuses to come to grips with it and at best is just kind of quiet about it, and at worst endorses it. I think the Republicans I would support today are more the exception than the rule. 

I’ve lived for a long time in Virginia. As I recall, [McAuliffe] was a pretty good governor. He’s a moderate Democrat. The Democrats have governed the state for the last two years with control of the state legislature. The state’s in pretty good shape. I have no big objections, I would say, to the McAuliffe Democrats running Northern Virginia and to McAuliffe himself, who I think is a serious guy and was a good governor. Youngkin fundamentally is unwilling to break with Trump and Trumpism. Some people can say in response, well, that’s just rhetoric. And I think it’s a fair point. I think it’s easier to vote for a Republican for governor than for Congress, because if you’re going to be in Congress, you’re going to be supporting [House Minority Leader] Kevin McCarthy. If you’re in the Senate, you’re going to be voting in conjunction with various Trumpists. That’s a more immediate referendum on Trump; obviously, a state-level race is different. If I were in Massachusetts I would vote for [Republican Gov.] Charlie Baker for reelection. Of course, Baker didn’t support Trump. 

JI: Before Trump was president, were there Republicans of whom you were skeptical? Or did you start to separate out each Republican candidate only after Trump came onto the scene?

Kristol: A little bit of the first, I would say, but much more after Trump came on the scene. I really don’t remember what I did in [the 2013 gubernatorial race]. I might have just sat it out. There were other times I didn’t vote for individual Republicans. I’d never been 100% a party person. There were parts of the party I disliked. On immigration in particular, I very much disliked the rhetoric of [former Virginia attorney general and 2013 Republican gubernatorial candidate Ken] Cuccinelli and then [2017 Virginia gubernatorial candidate] Ed Gillespie. Some of the economic policies had become irresponsible. The answer is, yeah, there were parts of the Republican Party I didn’t like, but Trump really brought it to a head. 

JI: Obviously, most Republicans do support Trump. In this political climate, would you find it possible to support Republicans who speak positively about Trump but who also support policy positions that align with your own? If a Republican expresses support for or praises Trump at all, does that mean you will oppose them?

Kristol: I think there are particular policies of Trump [that] people were totally entitled to praise, and that I myself might agree with, whether it’s deregulatory efforts or maybe the push for the vaccine. I have no problem with someone saying that or arguing that or giving Trump credit for that. There are other issues where I agree with things this administration’s done, distinct things Biden has done or Biden’s proposed. For me, the policies are individual, and you can support them. 

The overall governance of Trump — praising that, supporting the reelection, for me that was the real litmus test. You could have supported Trump in 2016. I think it would have been a big mistake, but you could have talked yourself into saying he’ll grow into the office, he’ll move beyond some of the demagoguery, and it’ll be constrained by the Republican establishment both on the Hill and in the Cabinet. To support him for reelection in 2020 really is pretty hard to swallow. I mean, Liz Cheney did — but to her credit, the moment it became really clear, after November 3, what he was doing, she turned on him. And Liz said she regretted supporting him and said she wouldn’t support him in 2024. That’s a reasonable position that I can live with. People who want to continue to say that it would have been right to reelect Donald Trump, and that it’s fine to accommodate Trump and Trumpism going forward — I find that very difficult to support. 

JI: Why did you opt to come off the sidelines in Virginia and endorse McAuliffe, when a lot of other alienated Republicans haven’t gone as far in publicly supporting McAuliffe or other Democratic candidates?

Kristol: I don’t think I’m going to move a whole lot of votes. They asked. I’m a very big believer in the privacy of the ballot. It’s a liberal country, liberal society, in the broad sense of liberal, and one of the aspects of that is you don’t have to be involved in every political fight or any political fight if you don’t want to be. In my work, I’m claiming to have thoughts about how democracy can be strengthened going forward. It doesn’t mean I have to be in every race. But I live in Virginia. I’ve expressed opinions about Virginia politics in the past. I just felt like once I got asked my opinion, it seemed a little ridiculous to say, ‘Well, I’m staying out of it.’ I’ve got opinions about voting rights legislation, I’ve got opinions about withdrawing from Afghanistan, I’ve got opinions about the Biden administration, and I don’t have any opinion about these two candidates running for governor of my state? I do have an opinion. I’m not saying it’s a very important opinion but I do have an opinion. So I’m happy to volunteer it.

JI: Have you or do you have plans to speak out in the same way about your member of Congress in Virginia?

Kristol: I knew Barbara Comstock when she was a member of Congress. And I said publicly in 2018 that I thought it was very important that the Democrats win the House. And I think I said I would therefore vote in my own district [Virginia’s 10th Congressional District], for the Democrat [Jennifer Wexton], though I know and like and respect Barbara Comstock. She was not pro-Trump, to be fair. And still, at the end of the day, she was a vote for Republicans in the House, and that would have meant a Republican House that wouldn’t investigate, in my view, the Trump administration appropriately. Could it be a little different in 2022? I suppose you could argue that Kevin McCarthy as speaker of the House isn’t that terrible, at least he’ll check Biden a little bit, but I think it’s pretty, pretty terrible, given the behavior on January 6th, and subsequently. So I expect to vote for the Democratic candidate here in this district.

JI: Now that in some ways you’re gravitating towards the Democratic Party, have you changed your views at all or found yourself questioning some of the views you’ve held on the foreign policy issues that you’ve been most vocal on throughout your career?

Kristol: Ironically, I’d say I’ve changed or rethought my views more on domestic policy issues, just because I feel like I’ve seen some things I didn’t want to see earlier on — a little bit on race, a little bit on some of the economic issues. Foreign policy, I haven’t really changed my views. And I’ve been critical of Biden for the withdrawal from Afghanistan. I always had views there that were more — people said it was neoconservative, or whatever — very consistent with liberal internationalism. We supported Clinton’s intervention in Bosnia in the eighth or 10th issue [of the Weekly Standard], and we were getting a lot of angry letters: ‘You’re supposed to be a conservative magazine, what are you supporting Clinton for?’ I’ve always viewed those views as sort of separate from American partisan politics. So, no. The short answer is — of course, there are particulars and errors in judgment and so forth. But not fundamentally, I would say.

JI: Looking specifically at the Iraq War, which most Democrats today would say was a bad idea, has that led you to rethink your views on the Iraq War at all? And whether, looking back now, that war was worth it?

Kristol: Look, obviously, if you supported it you’d be crazy not to have thought, rethought and worried about whether you were right. Obviously it wasn’t fought the way we hoped. We supported the surge, which I think, by the end of 2008, had created an acceptable situation in Iraq. Then it led to ISIL, which we then crushed. And now we’re back to a not-so-terrible situation, honestly, in Iraq today. Whether it was worth all that is a different question, obviously. So I guess I now would be open to people — I have friends who have said they think it was a mistake, I have other friends who don’t think so. I’m inclined not to think it was. I mean, of course, not having weapons of mass destruction would have changed everything. Knowing that [Saddam Hussein] didn’t have the weapons of mass destruction would have changed everything, but I didn’t know that, nor did others who were inside government. So I guess the answer is, on Iraq, I’m uncertain what the right choice would have been. It’s hard to rerun history and see what it would have looked like if we hadn’t intervened. I would say more broadly, on intervention, I will acknowledge Iraq was very difficult, and many things were done badly, if people on the other side will acknowledge that non-intervention in Syria led to hundreds of thousands of deaths and all kinds of terrible consequences, including the refugee crisis, which inadvertently helped to elect Trump in 2015, 2016. So there were costs either way, I guess I would put it. So I’m uncertain about Iraq.

JI: Looking within the Democratic Party, there are members elected in the past few years like Rep. Ilhan Omar (D-MN) who are not just critical of Israel, but opposed to the State of Israel. What do you make of their influence within the party? And how does that affect your views on the party as you move closer to it?

Kristol: It’s very important for Israel to have support in both parties. The Republican Party is quite pro-Israel. It’s pro-Israel in some slightly wacky ways occasionally, but whatever, it’s OK. Can’t complain about it. There’s a fight within the Democratic Party. I don’t know how much I can help in that fight because I don’t exactly have great Democratic credentials. In fact, a group I was associated with did try to make a case in Ohio [in the 11th Congressional District special election]. It was important which Democrat won that primary since it was clearly going to be a Democratic seat, and in fact, the pro-Israel Democrat won that primary. There are plenty of pro-Israel Democrats in Congress, more than the anti-Israel Democrats — and anti-Israel might be a little broad, but the people who don’t share my views on Israel, and there are a number of them in the Democratic Party. I don’t know if they’re really on the ascendancy. They certainly have been on the ascendancy on college campuses and among some groups, but they don’t really control that many seats; they certainly don’t control the Biden administration. If you looked in 2019 at the Democratic [presidential] candidates, there were my hawkish pro-Israel, pro-Bibi [Netanyahu] friends who would really internalize that Trump-Bibi connection, [who asked], ‘How would you even think about that party?’ and I’m looking to Joe Biden and Pete Buttigieg and Amy Klobuchar, and I’m thinking, ‘It’s not so bad.’ Now, [Bernie] Sanders would be a different story. But Biden won the nomination. 

And so I say to people who are uncertain about the Democratic Party and Israel, all the more reason to fight to define the Democratic Party on Israel. It’s not going to be a happy story if we have a pro-Israel Republican Party and an anti-Israel Democratic Party. Republicans are not going to win every election, though they’ll win most of the elections, probably, based on the last 20 years, though they only won the popular vote once. So you do not want to put all your eggs in that basket. I would say for people who are in between, you know what, the Republican Party is OK for now. Let’s strengthen the forces in the Democratic Party who are pro-Israel. And I would also say generally that goes along with the more internationalist view of foreign policy. I’ve always thought it’s hard to sustain a pro-Israel position if you’re against helping any other democracy but you’re only for helping Israel. That’s kind of the Trump Republican position. I don’t begrudge, if you’re the prime minister of Israel, you’ve got to work with what you’ve got to work with. And maybe you go along with that, you don’t criticize that, but in the longer run that is not a healthy position. I’m not with the Trump-Bibi faction in the pro-Israel community that thinks the Democratic Party is lost or hopeless. I would say, in fact, it clearly isn’t. It really matters who wins the Ohio 11 primary, it matters who wins a bunch of other primaries next year for the Senate and for the House. It matters, obviously, who serves in the Biden administration. It’s very foolish to just write off the Democrats.

JI: To that point about the Trump-Netanyahu wing, there are people who will say, ‘We will acknowledge that there are extremely problematic members of our own party, far-right extremists, but are they actually any worse than the Squad?’ There are a lot of comparisons made between those two groups.

Kristol: I think it’s slightly irrelevant. I could make arguments about why the Squad is a lot less in the center of the Democratic Party than those Republicans are in the Republican Party. I don’t think a lot of Democratic candidates are asking Ilhan Omar to campaign for them in their districts, whereas I think a lot of Republicans are very happy to show up with Marjorie Taylor Greene or Paul Gosar or someone like that. Or maybe not that many Republicans are. But what does it matter? At the end of the day, we need to fight both. There are obviously people who are Republican elected officials who have more of an obligation to monitor their own party and the same with the Democrats. And there are times when I wish some Democrats stood up more vocally against some of the Ilhan Omars of the world. But one thing about supporting Democrats is that I can support Democrats who do stand up against them. And you know what would help is electing Shontel Brown in Ohio 11, in Cleveland, and electing — it’s a state-level race, so it’s not quite the same thing — but electing Terry McAuliffe in Virginia. What kind of Democratic Party do we want? I’m happy with Shontel Brown, Terry McAuliffe, Eric Adams, Phil Murphy in New Jersey, Gavin Newsom in California (I’m not a huge fan of his personally but I think he’s pretty pro-Israel). But certainly at the congressional and Senate levels it matters who wins some of these open seats and contested seats in 2022 on the Democratic side. 

JI: On the Ohio front, I know that you have supported [Republican Senate candidate] Josh Mandel in the past, and so I’d be curious what you make of the campaign he’s running now. 

Kristol: It’s horrible and it’s embarrassing. [Mandel was criticized by the Anti-Defamation League for comparing mask mandates to the Gestapo, and he called ADL chief Jonathan Greenblatt a “kapo.”]

JI: To zoom out on the Israel issue, Bibi Netanyahu is no longer prime minister. I know that you have a relationship with him. What do you think his legacy will be as prime minister?

Kristol: I think mostly positive. He’s a very impressive person. He has his flaws, God knows, and maybe those flaws over time became more evident than the impressive parts. His policies were often different from his rhetoric. His policies were more prudent. The things that I would most hold against him were probably more of the corruption stuff. And then some of the demagoguery was bad, especially the last couple of election campaigns. I remember having a big argument with a very pro-Israel, hawkish, pro-Bibi, pro-Trump group of people in America. It was the day it became clear we were going to have the Bennett-Lapid government. And there was total hysteria among those people. ‘It’s the end of the world, you’ve got a weak, left-wing government in Israel, the Biden administration is going to pressure them, and they’re going to capitulate, and everything’s gone. We have to be in total opposition on both fronts: to Biden and [to Bennett].’ 

I remember saying, ‘Bennett is not really a left-winger. It’s not really a left-wing government. It looks like it’s going to have the same defense minister. Lapid is not particularly dovish on foreign policy, and he’ll be foreign minister. So what are we talking about here?’ We have an interest in the Biden administration being pro-Israel and the Israeli government succeeding and the administration succeeding in the U.S. We want a strong U.S. and a strong Israel. So maybe we could do our best to push for sound policies in both countries, and not pretend that it’s the end of the world if we have Joe Biden as president of the United States and Bennett as prime minister of Israel. There’s something a little childish about that. That’s not to say there couldn’t be something that happens in six months that I don’t like that either the Bennett government does or the Biden administration does. I think maybe people will calm down a little bit in the pro-Bibi, pro-Trump right, as they see the new reality. Or maybe not. People are so invested at this point in a certain analysis of things and a certain apocalyptic view of everything, and it’s hard to know who came back to reality.