Ukrainian refugees Julia and Miroslava walk away with relatives (R) who picked them up after they crossed the Ukrainian-Polish border on their way out of Ukraine at the Dorohusk border crossing, eastern Poland on April 6, 2022.
Christophe Archambault—AFP/Getty Images
April 30, 2022 1:00 PM EDT

Welcome to The Back Booth, a weekend edition of The D.C. Brief. Here each Saturday, TIME’s politics newsletter will host a conversation between political professionals on the right and the left, pulling back the curtain on the conversations taking place in Washington when the tape stops rolling. Subscribe to The D.C. Brief here.

There aren’t a whole lot of people who have navigated Presidents, Cabinet members and the top military brass into war zones without much advance warning, but two of them join The D.C. Brief’s Back Booth this weekend to talk about secret trips, Vladimir Putin, and ‘nerd prom.’

On the right, Alyssa Farah has been at the forefront of some of the toughest conversations in conservative politics. A former spokeswoman for the House Freedom Caucus, she joined the Trump Administration in a number of high-profile roles, including press secretary to Vice President Mike Pence, the Pentagon’s top spokeswoman, and White House communications director.

On the left, Johanna Maska cut her political teeth on Kansas Gov. Kathleen Sebelius’ team, and later as one of then-candidate Barack Obama’s top logistics fixers starting from the kickoff in Iowa. She later joined Obama’s White House staff, where she ran the press corps’ travel logistics on everything from day trips to Des Moines to multinational global visits.

The conversation over Zoom and email has been lightly edited.

Elliott: What are you seeing in Ukraine? You’ve both been inside as VIPs have gone into dicey spaces. It sounds like the cover of the Secretary of State and Secretary of Defense’s trip was blown and they still decided to go. What do those conversations sound like?

Maska: I remember doing some of those under-the-cover-of-darkness trips, and the moment that your cover is blown, Russia knows that you’re there. There was a decision made that it would be even worse had they not gone. So they figured out how to go, but they are really walking a very delicate line here.

Farah: I had exactly the same thought when I saw Zelensky announce it rather than the U.S. side, which is always how you would traditionally want a VIP trip to be announced. I haven’t gotten to hear insider information if this was coordinated. I did countless trips, one to Afghanistan that was unannounced, with Secretary Esper to announce what was the beginning of peace talks. At the last minute, we had to strip down our pool and our travel package because we were getting wind of threats to him.

That said, I think it was tremendously important that both the Secretary of State and Secretary of Defense went. The symbolism that we need to restore diplomacy by sending the Secretary of State, but also that we are active military partners of the Ukrainians and that’s what it signals by sending the Secretary of Defense. So both strength, but that hope for peace.

Elliott: Also it holds out a reward at some point with a possible Biden visit. Once you’ve given Zelensky a presidential visit, there’s nothing left to have come to the table.

Maska: Yeah, it’s an important kind of carrot. But you’re escalating our military engagement and our military has not been engaged. If someone is hurt or killed in Ukraine, there becomes even higher risk.

I hear a lot of politicians often throwing our government under the bus. But having seen it up close, I would say when you see the operations of the Secret Service and our military members and the flawless execution of some of these things that are extraordinarily high stakes, you learn to not underestimate America, not underestimate our service people, and know that they are really doing everything with the level of precision that we would want in our government.

Elliott: So we’re sending the diplomats to Ukraine. Going back, historically, to the 1700s, U.S. diplomats are taken care of by Marines. So we’re going to again have Marines at the gate of the embassy in Kyiv. I don’t know how U.S. officials can convince Moscow that this is not an act of aggression, putting a U.S. military member on Ukrainian soil with a weapon.

Maska: It is risky. I am sure that the Department of Defense and the Department of State had to work very closely to figure out whether it was worth the risk. Not to stand up for Ukraine, because obviously we are; we’re sending lots of military equipment. But rather to put U.S. personnel in that position, knowing that there’s still an active conflict going on.

Farah: And let’s be abundantly clear: the only solution to this is a diplomatic solution. It will be some sort of a brokered piece that requires diplomats to get to that point. There’s an important symbolism and strength to keeping U.S. embassies abroad. Our top diplomats, much like somebody who swears an oath to be in the military, know the true risks that they’re putting themselves in. There’s also an intelligence footprint that goes with them.

And on top of that, where is Putin right now? I know the Biden Administration is being very wary of anything that can be seen as escalatory. I think this should be framed as moving toward a solution, moving toward a brokered piece and what that looks like.

Elliott: Not asking you to betray state secrets here, but how well do we actually understand Putin?

Farah: I think that’s an open question. There have been rumors that are open-sourced for quite some time about his deteriorating health. I hate to ever get into things that are speculative, but I think it’s backed by enough open-source information that it does seem true, that he may be thinking very much about his legacy and what Russia looks like after he’s gone and how he’s remembered. And that makes for a very reckless adversary. So it’s a very, very careful diplomatic and military path we have to be on.

Maska: At the same time, China has stepped up its power. Right before this conflict, Russia and China said they’re going to work together on the issues that are going to dominate the next century: technology, the Internet space, clean climate technology. And I think they continue to grasp the question of whether the West will stay united. The Le Pen-Macron engagement can’t be ignored. The fact that Le Pen won with the youngest voters. I continue to get frustrated because a lot of Democrats in the U.S. will say the youngest generation is so much more liberal. The youngest generation feels very left behind. They don’t have pensions, they don’t have security in their jobs, they don’t have a government that has kept pace with regulating technology that has totally decimated industry.

Farah: Building off of that, there’s a growing nationalist populist trend around the world right now, but particularly in the West. They’re all different and unique, but it’s also not dissimilar from the nationalist popularist right. That we’re seeing on the rise in the U.S., which oddly has a degree of overlap with the populist left.

Elliott: Politics is a circle eventually. It’s not a spectrum, really.

Farah: Our generation down, the biggest thing I’ve observed is that they’re anti-institution and that’s the most common thread. And that becomes dangerous when you’re looking at threats to democracy that we’ve had in the U.S., from under my former boss, the efforts around Jan. 6th, but it’s also internationally. Other countries that are some of our closest allies in the West are feeling that same tension, and getting dragged into very similar dynamics to what we’re seeing.

Elliott: Shifting slightly here, but I’ve seen both parties sincerely try to do something on immigration, and it just always dies. You’ve both been on the inside as efforts with varying intensity came to the table. What is it gonna take in this country to get this immigration system right?

Farah: My belief is immigration has become the third rail of politics on both sides. You can’t even talk about a pathway to citizenship to dealing with the 11 million DACA and other populations existing in the U.S. at all without literally facing a primary and losing your place in Congress. You cannot talk about any sort of border security and enforcement without being seen as going against the ideas of people coming in and making it easy.

And that’s why I get so frustrated with my party talking about it in bigoted terms as though security is the only issue, and not recognizing this is a humanitarian crisis of people who are risking their lives from the Northern Triangle to come across the border into the U.S. And by the way, one in three women will be sexually assaulted on that journey. We absolutely need some kind of border security, but it’s not a wall. That’s not how we would deal with a military installation. It’s more checkpoints, it’s next generation technology, it’s drones, et cetera. And by the way, the cartels will dig under or go over a wall.

Elliott: John McCain had the line: build an eight-foot wall up, they will find a 10-foot ladder.

Maska: We didn’t do a good job, either, on immigration. We should have stood up for immigration. We should have stood for those human values. And I think that on our side, we also have the real challenge of there’s a lot of people who believe that immigrants have taken their jobs and, and actually, that is not true. Instead, what we did was such a short-term effort.

Elliott: Leader McCarthy seems to have gotten in a pass with his caucus in his first in-person session today. Alyssa, is there a 4D chess being played that I’m not seeing?

Farah: Kevin McCarthy seems to have more political lives than a cat, but as someone who was working for House conservatives in 2015 when he was denied the Speakership the first time, I think he still has an uphill battle to the gavel. The rightmost flank of House Republicans is poised to be the largest and most powerful bloc it’s been in recent history after the 2022 midterms. Keeping that rogue body of Marjorie Taylor Greenes, Paul Gosars, Matt Gaetzs, and so on in line to support McCarthy for Speaker will be a full-time job. That’s why he’s consistently making overtures to those individuals. Throw in a mercurial former President whose loyalty can flip on a dime, right-wing media like Steve Bannon’s War Room already calling for new leadership, and deputies (Steve Scalise and Elise Stefanik) who have their own Speaker ambitions, McCarthy is walking a tight-rope.

Maska: Honestly, we keep having the same, stupid, limited debate about President Trump. Not all of his ideas were bad but his actions on Jan. 6 were disqualifying. It doesn’t matter who it is in politics—if they don’t respect America’s institutions at their core, even if they seek to change them, that to me is unpatriotic, deceitful, and not worthy of how great America is and will grow to be. America is better than President Trump and I do hope more Republicans stand with Alyssa to make the future of the Republican Party. Just as I hope those of us who will lead the future of the Democratic Party stand up. Debating ideas will get us farther than covering the cult of personality. We play into it when we keep giving it oxygen.

Farah: McCarthy has in his favor that he is an incredible fundraiser who is working around the clock to grow the House majority. There’s wisdom to not firing your captain after winning the Super Bowl. But he will have to work overtime for the next year to keep former President Trump happy, understanding that one statement from Donald Trump could derail his speakership.

Maska: I keep thinking about Washington as it is versus Washington as it should be. Political leadership wins because they can fundraise. It’s the same on the Democratic side. Pelosi is an excellent fundraiser. Leadership isn’t kept because of how much one party has accomplished, working together with the other party to govern for the American people, but rather how much they can resist and milk the cash cow for their party.

Elliott: On a lighter note, you’re both vets of Nerd Prom, or as it’s officially known, the White House Correspondents’ Association dinner. Is this also a game of chicken? The Vice President has COVID, Dr. Fauci is skipping the event. If you’re running ops, who are you talking to about whether President Biden can still safely attend?

Maska: Nerd prom: Chicken or Squid Game? I’m certain the White House team is working closely with the White House physician, staff, and the various advance teams. The advance team should be asking the White House Correspondents’ Association many questions about protocols, but given you can’t put him in a bubble, every engagement is a risk. My guess: The President and others around him would be pushing to go. Others are voicing concern. And there’s a fiery debate within the team—go or don’t go. What looks worse, getting COVID from the dinner or not going?

Farah: Washington is still recovering from the super-spreader that was the Gridiron Dinner. I think it was wise for Dr. Fauci, as a public health professional, who is also an octogenarian, to stay home and set an example for high-risk individuals. I’m sure the President’s doctor, Secret Service, ops, and the White House medical unit are giving very strict guidance to WHCA about the President’s movements and interactions he will have with others. Traditionally, for an event of this nature, the President doesn’t show up a minute before he has to, and is ushered into the Hilton likely through service corridors and elevators, and only takes the stage when he absolutely has to. If I were on Team Biden, I’d be telling WHCA we aren’t doing any backstage photos, handshakes, hugs, etc., to minimize his risk. But once he’s on stage it’s a fairly low risk environment for him. I think there’s wisdom to getting back to normal life and letting individuals make their own assessment about their risk.

Elliott: Thank you both for being so generous with your time.

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