Two Questions with Karoline Leavitt
What it’s like in the front row of the White House briefing room.
I got a phone call from a White House spokesperson on Wednesday.
The White House was planning to hold a press briefing in two hours, and they wanted to call on me for the first question. Could I make it?
I cleared my schedule.
I threw on a suit, and immediately started thinking about what I wanted to ask Karoline Leavitt, the White House press secretary.
There was the SAVE America Act, which had been the topic of that morning’s newsletter. I could go super-niche and ask about the Senate filibuster, or about whether President Trump would want Senate Republicans to overrule the chamber’s parliamentarian if she says election reform can’t be done through the reconciliation process. No, too specific.
TSA lines were snarling through the airports: I could ask for an update on the Department of Homeland Security shutdown negotiations. But what were the odds she’d have an update to share?1
Hoping I’d be able to ask a follow-up, I ultimately settled on two questions:
First, I wanted to ask about war powers. The war in Iran is now almost a month old, and I felt like the idea of the president seeking congressional authorization had come up a lot in the early days of the conflict, but pretty much been dropped since then. Of course, there are now peace talks, which may lead to the war ending — but there are also signs of potential escalation.
Thousands of U.S. troops are on their way to the Middle East, and President Trump is reportedly considering an operation to seize Iran’s Kharg Island, which would require a ground invasion. I wanted to know if the war stretched on long enough, or if it started to involve ground troops, whether there was a point at which President Trump would commit to seeking congressional authorization.
Second, I wanted to ask about the youth vote. In the 2024 election, President Trump made significant gains among young voters, in no small part because they wanted lower prices and an end to foreign wars. Now, of course, Trump is engaged in a war that is causing prices to go up. Many young Trump supporters have been growing dissatisfied as a result.
I wanted to ask what President Trump’s message was to these young voters who had supported him in 2024, but now feel the administration isn’t going how they expected.
My hope was that these two questions would a) be newsworthy, b) be in keeping with the topics I cover in this newsletter (like separation of powers and shifting political coalitions), and c) take advantage of the fact that not many 24-year-old journalists get to ask the White House press secretary a question. I wanted to try to bring a Gen Z perspective into the briefing room.
You can see my questions and Leavitt’s responses in the video below. On the first question, she told me that congressional authorization for the war in Iran is “not necessary because we’re currently in major combat operations” — a military term, but not a legal one — and that all briefings that Congress had received had been given strictly “as a courtesy.” She didn’t lay out circumstances under which Trump would seek authorization, though she didn’t rule it out either, pledging that the president and the administration “will always abide by the law.”
On the second question, Leavitt said her message to young voters was, “President Trump is doing this for you,” to ensure that U.S. troops in the Middle East, “many of them young people themselves,” are “no longer threatened by a rogue terrorist regime.” She said that the spike in gas prices would be a “temporary short-term fluctuation” and that “they’re going to go right back down when this is over.” Here’s our full exchange…
In today’s newsletter: I want to take you inside the White House briefing room, explain what it’s like and how it works, talk about how the press briefings have evolved, how useful I think they are in the age of Trump, and what led to me being able to ask the first question.
This is the type of behind-the-scenes content I always try to offer paid subscribers, whether it’s at the Supreme Court, a presidential debate, or a nominating convention. One of my goals with Wake Up To Politics is to take you inside the halls of power and give you a sense of how our politics really work.
If you aren’t one already, I hope you’ll take this opportunity to become a paid subscriber. As I’ll explain below, I was in the briefing room’s “New Media” seat, which more often than not — I run the numbers below — has gone to highly opinionated outlets. Someone recently sent me a database they built of top figures in independent media (political podcasters, Substackers, social media influencers, etc). They had Claude, Gemini, and ChatGPT organize each of the commentators on a left-right spectrum and averaged out the answers between 0 to 50 in either direction, from Hasan Piker (50D) to Candace Owens (50R).
Out of 97 media figures, I was one of only two to score a perfect 0, right in the center.
I am glad that there is a growing ecosystem of “new media” outlets, and that the White House is giving some of them recognition. But I fear for the future of media if voices are much more clustered towards the 50Rs and 50Ds, with fewer and fewer places to find the 0s: unbiased reporters who are covering politics through a non-partisan lens. I truly believe we’re building something special here at Wake Up To Politics — and apparently three AI models agree with me!
If you also want “new media” spaces to include some non-partisan voices, I hope you’ll upgrade to a paid subscription to ensure WUTP can keep going. (Trust me: going “50R” or “50D” is a much better business model.) It’s only with your support that I’m able to end up in places like the White House briefing room.
Plus, a paid subscription means you can come along with me when I do. Speaking of, let’s take a trip into the White House and learn the secrets of the James S. Brady Briefing Room…
