What A Day - Trump vs Reddit: Free Speech In The Balance

Episode Date: April 20, 2026

President Donald Trump and Co. have historically claimed to be all about free speech. But maybe Trump only cares about free speech when he likes what's being said. Earlier this month, The Intercept reported that the Department of Justice is taking Reddit to court to force the massive social media platform to unmask one of its users. Why? Because Immigration and Customs Enforcement has been desperately trying to identify the user who said stuff ICE doesn't like.To learn more about what's going on with Reddit and the Justice Department, we spoke with Ryan Devereaux. He's an investigative journalist for the Intercept.And in headlines, FBI Director Kash Patel says he's going to sue The Atlantic for a 'defamatory article', companies that paid Trump's emergency tariffs can start claiming refunds, and Energy Secretary Chris Wright brings more bad news about gas prices.Show Notes: Check out Ryan's piece – https://tinyurl.com/5akbsrww Call Congress – 202-224-3121 Subscribe to the What A Day Newsletter – https://tinyurl.com/y4y2e9jy What A Day – YouTube – https://www.youtube.com/@whatadaypodcast Follow us on Instagram – https://www.instagram.com/crookedmedia/ For a transcript of this episode, please visit crooked.com/whataday

It's Monday, April 20th. I'm Jane Koston, and this is What a Day. The show starting off the week with something genuinely fun. New York City, Mayor is around Mamdani and former President Barack Obama meeting for the first time to read to pre-kindergarteners in the Bronx on Saturday. And those kids were well aware of who they were getting to see. What's his first name? What's his first name? First name mayor, last name I'm daddy. Check's out. On today's show, President Donald Trump says he's too busy to be depressed.

And where in the world is FBI director, Cash Patel? Seriously, where is he? Maybe in court soon. Well, let's start with free speech. President Trump and his administration have claimed to be really, really into free speech. For example, there was this campaign video from December 2022. If we don't have free speech, then we just don't have a free country. It's as simple as that.

If this most fundamental right is allowed to perish, then the rest of our rights and liberties will topple, just like dominoes one by one. They'll go down. And there was that executive order he signed on day one back in the White House in 2025, aimed at, quote, restoring freedom of speech and ending federal censorship.

All evidence that Donald Trump cares a lot about free speech. Well, sort of. Or, as he put it in a September 2025 press conference from the Oval Office. I'm a very strong person for free speech at the same time. Yeah. See, Trump cares about free speech, except if he doesn't like the speech. Like in that September press conference, where Trump went on to say that if someone says mean things about Donald Trump, that doesn't count as free speech. Quote, when 97% of the stories are bad about a person, that's no longer free speech.

That's just cheating. And now that goes for people who say mean things about immigration and customs enforcement. even anonymously. Earlier this month, the Intercept reported that the Department of Homeland Security took Reddit to court to force the massive social media platform to unmask a user critical advice. And now the Department of Justice is even summoning Reddit to appear before a grand jury in D.C. all to identify that one person. To explain how this is even possible, I spoke to Ryan Devereaux. He's an investigative journalist for The Intercept. Ryan Devereaux, welcome to What Today.

Hey, thanks for having me. So this story is ridiculous. Let's start with a time frame that involves this Redditor, who was referred to as John Doe in legal documents. When was this? And what did this John Doe purportedly post on Reddit that made the Trump administration this mad? So it's a complicated story. It sort of starts back at the beginning of last month. John Doe received a notification from Reddit that the company had received a request

from the government for a lot of information on John Doe's account, information that would identify who this anonymous user of this Reddit account was. This request came in the form of what's known as an administrative subpoena or an administrative summons. It's a powerful legal tool that's been around for a long time and it's typically associated with, you know, internet-related crimes, child endangerment, human trafficking, that sort of thing. But in the past year, the big social media companies have seen a really significant uptick in these requests coming in for social media accounts that are posting information about the Trump administration's immigration crackdown. Administration officials have argued that there are these anonymous accounts

all over the place that are doxying federal law enforcement, revealing the names and identities of agents, that sort of thing, reporting on operations in real time. But there's a kind of pattern of these administrative subpoenas targeting people who seem to be just engaged in venting about the government. And that seemed to be what may have happened last month. So John Doe gets this request asking for all this data. They have no indication what exactly they posted that tipped off or ticked off the federal government. John Doe is from the Pacific Northwest. There had been some, you know, battles in the Northern District of California, a lot of these tech companies are based over these administrative subpoenas.

So Doe gets the Civil Liberties Defense Center to come on as legal representation. They file a motion to quash this subpoena, which these advocates have been doing with some success in the last several months. Basically, the government asks for data. Lawyers say they go to a federal court, they say, and especially in the Northern District, look, we think that this is overly broad requests. This is, you know, tiptoeing into First Amendment protected activity. And the government has typically been withdrawing its requests for information when challenged in federal court. But what happened in this case that was unusual was the government let them know, hey, we're withdrawing this.

But then just a few days later, Reddit itself gets a notification. This time it's not coming from the ICE field agent, which is how this whole thing started. It's coming from a special assistant U.S. District Attorney, not in California, but in Washington, D.C. And this is not an administrative subpoena, it's an actual grand jury subpoena asking the company itself to appear before a grand jury in D.C., which is a pretty significant turn of events and in the minds of many privacy advocates, a sign of an escalation in the government's efforts to unmask these folks who've been criticizing the administration's immigration crackdown. Now, before we get into the grand jury situation, I want to get back to something important. What did John Doe allegedly say? Yeah, so we don't know for sure what it was that triggered this whole thing. But John Doe basically turned over their account to their attorneys to review.

And the attorneys found three different posts, which they think maybe had something to do with this. There was a subreddit conversation back at the beginning of January. Local media in Minnesota had revealed the identity of Jonathan Ross. the ICE officer who shot Renee Good. There was a conversation in a subreddit about that fact. It was literally a link to an article and people were chiming in. And John Doe chimed in. John Doe described biographical information about Ross that was circulating at the time.

Where he had lived, the fact that he had grown up out of state had lived in Minnesota for a while, John Doe said that they hoped he would end up in state prison. There was another post where some, somebody had asked what they should put on a protest sign that they were taken to a nice protest. John Doe suggested the lyrics from a song that I have here. It's a folk punk song. There's not even swear words in it. And then the third post was John Doe posted the TSA sucks and everyone knows it.

Those were the spiciest posts that the attorneys could find. We don't know for sure if there's something else out there that we don't know about. But this is all that the attorneys can find. I think I've said way meaner things about ICE or TSA. I'm sure lots of people listening probably have said some things. Have other Reddit users been pursued by the government for saying things people say on Reddit? Yeah, to the extent that we know anything about what's going on with this grand jury,

it's all under steel, it's all very secretive. But as I mentioned, over the past year, there's been this surging requests going to social media companies for information on anonymous accounts that are posting about immigration enforcement. And Reddit, in fact, in their most recent transparency report noted that the first six months of 2025, they received more requests from law enforcement than they've ever received at any point before in reporting. And you've got to remember that early 2025, that's before Renee Good. That's before Minnesota. So we'll have to wait to see what the data looks like when they get a little bit more information about these type of requests

later in 2025 and early 2026, but it's quite clear from these companies that there's a pattern of immigration enforcement federal agents looking for information about people who are posting about them, which is something that we have not seen in recent years and suggest a pretty targeted effort by the administration to go after its critics, which is consistent with a lot of the sort of national security priorities that the administration, particularly Stephen Miller, has outlined. Now, let's get back to what happened to John Doe. You said they fought off an administrative subpoena, but lo and behold, Reddit was asked to appear at a grand jury and asked to reveal John Doe's identity. What comes next and what's its stake at this point? For folks who don't know, grand jury, maybe it sounds like, you know, jury, it sounds like trial, that sort of thing. But that's not what a grand jury is. Grand juries are convened for the purpose of bringing, federal charges. The fact that, you know, that the government did decide to summon one of the largest

tech companies in the world with 120 million some daily users who all sort of come to that site, you know, relying on the sort of anonymity feature of it. I mean, it's kind of what Reddit is known for. The fact that the government saw fit to bring a company that big with that many users into one of these secret panels. that somebody seemingly posting rather tame posts about ICE had something to do with. That is extremely, you know, suspicious, I guess, mysterious. I was talking to a colleague of mine, and I just can't get over, you know, the Trump administration has claimed to be the most free speech administration ever.

We knew that wasn't true with regard to pro-Palestinian speech. But what gets me about this is that this is speech not about a foreign, policy issue, this is speech about government agencies. This is the kind of speech that we would have heard from conservatives under the Biden administration complaining about the state when it came to COVID lockdowns or, you know, how people talk about TSA all the time. What do you think it says about the government that they are willing to go this far? Bringing in a assistant U.S. attorney to go after Reddit to unveil someone who said, such anodyne stuff. Like, what do you think it says about the safety of speech under this

administration? I think it just underscores what the administration has been saying in ways large and small for the past year. You know, late last year, the Trump administration articulated a new sort of national security vision that put up direct sort of sites on what they consider anti-American sentiment, especially on the, on the sort of in the, sort of in the, realm of immigration enforcement has been, I've covered this stuff for a decade. It's been as intense as anything I've ever seen. It was on the ground in Minnesota earlier this year. And the intensity of emotion that people are feeling about what they have seen in the past 12 to 13 months is really extraordinary. And they're letting it out. And the government seems to

have a problem with that and is taking actions. Ryan, thank you so much for joining me. Thanks so much for having me. Appreciate it. That was my conversation with Ryan Devereaux, investigative journalist at The Intercept. We'll link to his piece in the show notes. Unlike Donald Trump, we love free speech. We can't get enough of it.

If you agree, make sure to subscribe. Exercise your right to free speech by leaving a comment and a five-star review on Spotify and Apple Podcasts. Watch us on YouTube and share with your friends. More speech to come after some ads. What a day is brought to your podcast. by aura frames. You just got home from an amazing trip with your best friend, one neither of you ever want to forget. Why not give your friend the gift of memories with a brand new aura frame? With aura frames, you get free unlimited storage, add as many photos and videos as you want. And you can

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When do you think a to try? realistic for Americans to expect that gas will go back to under $3 a gallon? I don't know. That could happen later this year. That might not happen until next year. But prices have likely peaked and they'll start going down. As the U.S. continues its war in Iran, Trump's energy secretary, Chris Wright, delivered great news on CNN Sunday to all the people who voted for Trump because he said he'd lower gas prices. On Sunday, the U.S. attacked and seized an Iranian-flagged vessel near the Strait of Hormuz. Iran's military headquarters called the movie Violet,

of the ceasefire and said, quote, Iran will respond soon. President Trump has said negotiations with Iran will resume in Pakistan on Monday, though, as of this recording, neither Iran nor Pakistan have confirmed. Iranian state media has claimed that unnamed sources suggest the talks won't happen. Trump threatened to destroy civilian infrastructure in Iran if it doesn't take the deal that the U.S. is offering, which, in case you need a reminder, is a war crime. The fragile ceasefire between the United States and Iran is due to expire Wednesday. Remember how earlier this year the Supreme Court ruled President Trump's emergency global tariffs were unconstitutional?

I certainly do. And then in March, a judge at the U.S. Court of International Trade determined that companies subjected to those tariffs were entitled to money back. Well, the time for reconciliation has come. A refund system for businesses is scheduled to lunch today. According to U.S. customs and border protection, importers in their brokers and their brokers, will be able to start claiming refunds through an online portal. If the agency approves a claim, it says it will take 60 to 90 days for a refund to be issued. Of course, the government expects to process the refunds in phases.

CBP has noted in court filings that importers paid more than $150 billion in tariffs. And while that's all fine and dandy for the companies, you know who's not seeing any cash back in this process? You've guessed it. The consumer. Me and you. FBI director Cash Patel says he plans on suing the Atlantic. The magazine published an article last week, citing FBI employees who say Patel has been drunk on the job and sometimes just doesn't show up for work. Here he is speaking to Fox News's Maria Barteromo on Sunday. Maria, I'm happy to announce on your show that we're not going to take this laying down. You want to attack my character?

Come at me. Bring it on. I'll see you in court. I can't wait. The article, which came out Friday, says that on April 10th, Patel was unable to. to log into his computer and had a, quote, freak out, thinking he'd been fired. It turned out he hadn't, but he might be soon. One FBI official told the Atlantic, quote, we're all just waiting for the word. The article claims over 20 sources, say Patel is, quote, erratic, suspicious of others,

and prone to jumping to conclusions before he has necessary evidence, which is exactly what you look for in someone leading one of the most powerful law enforcement agencies in the world, right? President Trump signed an executive order on Saturday to speed up reviews of certain psychedelics. Among those drugs is Ibo Gain, a controversial drug that has recently been embraced by combat veterans and conservative lawmakers. All of those drugs are still illegal in most states but are being studied for their potential to treat opiate addiction and mental illness. Ibogan, because it's so important and experienced an 80 to 90 percent reduction in symptoms of depression and anxiety within one month. Can I have some please? I'll take whatever it takes. I don't have time to be depressed.

You know, if you stay busy enough, maybe that works too. I, for one, do not want to see Donald Trump on psychedelics. Or busy. Previous studies of Ibogaine have been discontinued due to its potential to trigger fatal heart problems. Trump said he signed the order after receiving a text message from Joe Rogan asking him to look into it, which checks out at an almost spiritual level. And that's the news. That's all for today. If you like the show, make sure you subscribe, leave review.

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