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When we launched Regulator two months ago, the premise was that I’d write about the collision between Big Tech and Big Government. The key word was collision. Tech and politics no longer existed as separate planets that would occasionally cross paths — they were now crashing into each other in very messy and dramatic ways. The plan was to write a column about one subject a week that talked about a recent tech / politics collision.
But dear god, there are so many big events that happened over the last week, and it would be remiss of me to ignore any of them. And in fact, the biggest, most newsworthy political events of the past few days were inseparable from The Verge’s core reporting on tech. Here are the ones that have been stuck in my brain for a while…
TikTok, #Freedom edition: After several months of delays, there is finally (maybe) a deal in place to bring TikTok to America. The current plan, according to the White House, is to sell US operations to a consortium of Trump-allied investors, including Lachlan and Rupert Murdoch of News Corp, Larry Ellison of Oracle, and Michael Dell of Dell Computing. (Unlike recent investments, the US government will not have a stake in TikTok’s US operations.) Several issues are still under discussion — primarily whether the Chinese government will allow the deal to go forward. (As of Tuesday, the Chinese government has not formally acknowledged the executive order.)
For investors, TikTok’s massive user base and gargantuan pile of user data is its most valuable asset. But for President Donald Trump and his political allies, who won over many young TikTok users during the 2024 election, the most valuable part of the app may be its recommendation algorithm — one that they viewed as the friendliest to MAGA influencers, especially after sites like Twitter and Facebook began cracking down on their content post-January 6th. “People on the right, especially young people, were appreciative of TikTok for being around and not canceling people and still paying people out,” Vish Burra, the former communications director for the disgraced Rep. George Santos, told me back in April.
Under the current deal, ByteDance will still retain control of that algorithm and lease it to its US counterpart. But if Trump’s comments indicate anything, he wouldn’t be unhappy if it could nudge TikTok’s recommendations in a MAGA direction. “If I could make it 100 percent MAGA, I would. But it’s not going to work out that way, unfortunately,” Trump said, adding that, “every group, every philosophy, every policy will be treated fairly.”
Jimmy Kimmel Live! returns: The first part of this saga was heavily shaped by the power that the FCC has over broadcast: Brendan Carr threatened to revoke TV station licenses over Kimmel cracking a joke about Charlie Kirk’s killer, Nexstar and Sinclair caved, and ABC parent company Disney immediately suspended the show. But Kimmel’s triumphant return days later wasn’t just a sign that corporations might protect their talent’s free speech during Trump 2.0 — it was also a case study in the declining relevance of broadcast television and the companies that control it.
According to overnight numbers from Nielsen, Kimmel’s return episode drew a staggering 6.2 million viewers the night it was aired live on television — four times its normal viewing audience, despite only 80 percent of television stations airing it. (Nexstar and Sinclair both preempted it with other content.) But those numbers are dwarfed by internet viewership. Fifteen million people watched Kimmel’s monologue on YouTube the next day.
Portland versus MAGA, part 2: Over the course of last week, residents of Portland, Oregon, began seeing a notable surge in federal agents in the city. Shortly after local government officials told residents to remain calm, believing that ICE and DHS were trying to bait them into a fight, Trump authorized the National Guard to use “full force” to protect federal agents in the city.
While Trump has sent federal agents and the National Guard to other cities, citing alleged violence in those cities, Portland holds a special place in MAGA’s heart for being their favored hub of “antifa violence.” The decidedly liberal city was home to some of the earliest clashes between far-right militias and local antifascists starting in 2017, culminating in notorious fights between local residents and federal law enforcement during the George Floyd protests in 2020.
Below, I chat with The Verge’s features editor Sarah Jeong, who’s based in Portland and covered the federal invasion of the city back in 2020. But before that, here’s this week’s latest…
“The Trump administration just can’t stop leaking its chats”, Emma Roth: Signalgate was just the beginning.
“Can Google be trusted without a break up?”, Lauren Feiner: As long as Google still has the means and incentives to accrue dominance, the DOJ argues, it will likely do so again.
“Trump’s new H-1B policy caused short-term panic — and will cause long-term chaos”, Felipe De La Hoz: Tech companies like Amazon, Google, and Microsoft rely heavily on high-skilled work visas. What happens when they become less attainable? Do engineers and doctors stop coming to the US?
“The TikTok deal raises more questions than answers,” Emma Roth and Lauren Feiner: The deal to save TikTok shines a light on the Trump administration’s disregard for the law.
“Microsoft blocks the Israeli military from some cloud and AI services”, Tom Warren: The Guardian revealed last month that Microsoft’s services were being used for mass surveillance of Palestinians.
“Silicon Valley’s latest argument against regulating AI: that would literally be the Antichrist”, Tina Nguyen: This is a real thing Peter Thiel told a group of tech professionals recently.
“A city full of angry, angry libs”
Tina: What was the aftermath of 2020 in Portland once Trump was gone and Biden came in?
Sarah: People were more radicalized than ever. I don’t know to what degree that influenced the election. The protests were in the lead up to the 2020 election, and all of this was concurrent with covid. Covid drove a lot of the energy around the protests. People were unhappy with their lot in life because of covid. It was just miserable. It also meant that people were really willing to forget what happened with the feds in 2020 because no one wanted to think about covid. That is something that no one wanted to mentally return to. You also had a minor local depression because a lot of places shut down because of covid. There was a lot of rhetoric around Portland being blighted by the protests, but a lot of that was just covid.
There was a big rightward anti-homeless swing in local city politics in the immediate aftermath of 2020, but that has just recently corrected to a big leftward swing. You’ll see that reflected in local journalism saying that right now, the socialists on the City Council have an outsized presence in driving policy in the city.
Is the presence of a more actively socialist local government playing a role in drawing the Trump administration’s eyes back onto Portland?
I’m not sure. I think that Trump has always had a shadow perception of Portland, driven mostly by social media and Fox News. And I don’t think he has any fucking clue about what’s happening in this city. If you look at what happened last time, he was hyper-focused on Seattle, and then suddenly the DHS switched its own attention to Portland and then the president’s own social media account switched over to paying attention to Portland. He lost in Portland last time. He’s still pretty sore about it, is what I would guess. I don’t think he really cared that much about Portland. I think someone at DHS did.
I mean, there’s a lot of right wing rhetoric around, quote unquote, “violent Antifa in Portland.” That seems to be the prevailing meme that has not really gone away. And now all of the meme guys are in DHS and the Pentagon.
Last time, there was this early memo inside DHS that outlined the justification for invading Portland. I think there must have been a meme guy that decided to point their sights on Portland, especially because the justification that they pulled out was really funny. They cited the destruction of two statues. But neither of them are actually on federal property. One was the local German American Society and the other one was at a high school. Neither of those are federal properties, so it’s not really adequate justification. It just conflated a whole bunch of minor piddling things. Someone just really wanted to build a case for going up to Portland.
The current case right now seems to be much weaker than it had been in 2020. Does antifa still even have a presence anywhere?
The visual indicators of antifa are still very active here. You still see the black and red flags, you see the downward pointing arrows, you see people wearing black bloc at protests. And you also see that mixed up with the more normcore lib stuff, which is like, No Kings or whatever. But I would say that antifa still exists here. It’s just that you don’t see as much of it because it’s crowded out by how many normies are also out protesting.
So it’s enough of a presence for someone to point at it and go, hey, there’s Antifa, but not an actual presence.
There isn’t a stigma around being antifascist in Portland. I got my stupid little soy milk latte this morning and there was an old man with the red and black flags as a laptop sticker. The local soccer fan club, one of their songs is to the tune of “Bella Ciao,” and it has been forever. Like, the city is not a city that shies away from being perceived as leftwing radical. George H.W. Bush gave us the epithet of “Little Beirut.”
Legally, would the Portland city government and Oregon state government be able to resist federal takeover? Trump had threatened Boston and Chicago, and I think Chicago told them successfully to fuck right off.
At the state and municipal level, you just don’t have the same resources as, say, Chicago. We have a Democratic governor, but the Democratic governor has not shown a terrible amount of spine, generally. She actually ordered all of the flags to go half mast for Charlie Kirk. Not all of the governors did this.
[Note: Oregon has now sued to block Trump deploying the National Guard.]
Also, the last time, local police were not supposed to coordinate with the feds, because the feds were tremendously unpopular here. No one here was pro-fed. But nevertheless, people were sure there was some sort of connection between the feds, the police, and also the local militias. There was this suspicion that these three groups were all in it together. I don’t think that there was ever a proper smoking gun, but I don’t think that people here in Portland trust the cops to take their side.
Oh, are the militias back?
You know, they’re afraid of Portland. That’s one thing about the persistent lie that Portland has burned to the ground: all of the fear-mongering around Portland being a war-torn hell city has kept the agitators out. To be fair, the right wing has a non-zero fatality rate here in Portland. The one major instance of left-wing violence was in 2020, here in Portland — someone was shot and killed by a guy who identified himself as an antifascist.
So I guess they’ve been replaced with ICE. Have they been given way more authority to unilaterally this time than the feds were last time?
It’s a weird one. The order that was issued last time was about protecting federal monuments. There weren’t really any monuments that they were protecting, but basically the justification was: people are on federal property and we can do whatever we want with them. There’s an interesting thing about the geography in which the protests took place. Basically, the local cops’ building is next door to a federal courthouse, and both were across the street from these wide open park blocks. So if people were trying to protest local cops, like they did during the George Floyd protests, that would be an obvious area in which to protest, but they would unknowingly stray onto federal property. As a result, that became a justification for the federal crackdown, in order to “protect federal property.”
The current nexus of activity is in a different part of town that isn’t as wide open. It’s compressed in a really weird way, and right next to a freeway exit too. ICE is confined to a much smaller space to defend, but there’s also less space around it to protest.
“We have to go after antifa” has the potential to become a bigger remit than “we need to protect federal monuments.” Is that legal? Is that constitutional? I don’t think so. But does that matter? Maybe it just doesn’t matter. Certainly, it’s not something that would be allowable in the America I know, but that’s not an America that exists presently.
And here’s the other wrinkle. The ICE building where people are protesting this time is right next to a fucking Tesla dealership.
I know, right? The Tesla dealership’s not super accessible from the ICE building, so that’s the one saving grace. You’d have to troop up around in a goofy way with the sidewalks.
Final question: what do you think happens next? Does Portland start protesting again? Does Trump have more of an animus to send even more federal agents into Portland? What does this upcoming clash look like?
So, last week in Portland, Sen. Jeff Merkley, our mayor and city council members held a press conference and urged Portlanders to stay calm and not rise to the bait. The federal government is really eager for a fight to break out, and the local government thinks they’re trying to bait Portland into providing a justification for a greater crackdown. I will say that last time things really popped off, it was the news about the van abductions that radicalized the entire city. That is when people really started coming out. You would see just a massive number of people.
Right now, the city’s very angry. It is a city full of angry, angry libs. Like, you just walk around and you can see yard signs that are like, “Stop fascism” or pictures of Elon Musk saying “Elon Musk is a fascist.” Sometimes I drive past intersections and the intersections are full of old people, holding signs that say “Fuck Trump,” “Trump is a fascist,” “No Kings,” et cetera. And it’s like a Saturday, I’m trying to get groceries, and they’re just doing weekend protests every single week. That’s the city this is. You saw older folks and normie libs turn out last time, because the van abductions were just a shade too far for them. So I think what happens next depends on what Trump does next. And that’s much harder to predict than last time, because the threshold for what’s crazy is higher now.
And now, time for Recess.
Last month, tweenage jewelry chain Claire’s announced it was filing for bankruptcy and planned to close over 900 stores. In the Chapter 11 hearing, Kirkland & Ellis partner Joshua Sussberg mentioned that he, too, had undergone the classic coming-of-age ritual: getting his first ear piercing at Claire’s.
“At the end of the hearing, I said, ‘Your honor, we are focused on preserving jobs and keeping stores open for a long time so many people can get their ears pierced. If we can get a deal done, I am willing to get my ears pierced,’” Sussberg told American Lawyer.
Fast forward to a few weeks later:
