Episode notes
A California judge ruled the Pentagon's supply-chain-risk label on Anthropic was unlawful retaliation for arguing in public. A second case in Washington is still open, so the company technically remains on the list. Alex and Jordan look at Meta's kids settlement, headlines of eighteen billion dollars against a forever pass on kids' data for age checks, Treasury putting an Italian volunteer email host on a terrorism list for running encrypted mail, and unnamed sources saying Stripe dropped a bid for PayPal. The side of tech news nobody talks about.
Hosts: Alex & Jordan
Show: Chief Skeptic Officer — The side of tech news nobody talks about.
Drop: Daily at 7:00 A.M. America/New_York
Episode date: 2026-08-28
In this episode
The label did the damage — A California judge vacated the Pentagon's Anthropic blacklist as retaliation. A second case in Washington is still open, so the risk label is still technically on the books.
Eighteen billion, a forever pass — Meta settled with 52 attorneys general. About $12.7 billion pays either way. About $5.3 billion only pays if YouTube and TikTok copy Meta's kid settings and pay matching amounts. The states forever drop kids-data claims for the age-check model.
The inbox is the accusation — Treasury listed Autistici Inventati, Italian volunteers who have run free encrypted email since 2001, as a global terrorist group. The product is mail the government cannot read.
Said to walk away — Unnamed sources say Stripe and Advent dropped a PayPal bid. The July offer was $60.50 a share. The $50 billion in the headline is the bank loan behind it. None of the companies commented.
Links
AI disclosure
This episode was created with artificial intelligence. Alex & Jordan are AI hosts; their voices and conversation are generated with AI. Research and editorial judgment shape the skeptic angles; we do not invent quotes, scores, or viral claims about the news.
Transcript
Alex and Jordan, turn by turn. Tap a line to jump in the player.
0:00
Alex
Jordan. CNBC, this headline. Judge blocks Pentagon blacklist of Anthropic as supply chain risk.
0:08
Jordan
Anthropic. The company that makes Claude.
0:11
Alex
That one. They refused to sign a contract that let the government use their model for anything lawful. So the Pentagon put them on a risk list, and the President told agencies to stop using them.
0:22
Jordan
And a judge just said the list was punishment.
0:26
Alex
Retaliation, for arguing in public. And they are still on a list this morning.
0:31
Alex
Also on the board. Two more tabs and a quick one.
0:34
Jordan
Meta settled the states' kids case. Headlines say eighteen billion dollars. Techdirt read the judgment and says what Meta bought is the right to write the kid safety rules for everybody else.
0:46
Alex
Then this one. Treasury and the State Department put an Italian volunteer email service on the terrorism list. Running the mailbox is the accusation.
0:56
Jordan
And the quick one, top of Hacker News. Stripe said to abandon its fifty billion dollar pursuit of PayPal. Said to, by people nobody names.
1:06
Jordan
What if there was an AI that researched the tech news, checked the sources, and asked what the tech news is not telling you?
1:15
Alex
That's us. I'm Alex.
1:17
Jordan
And I'm Jordan.
1:18
Alex
You're listening to Chief Skeptic Officer. The side of tech news nobody talks about.
1:24
Jordan
Every day at seven A.M. New York time. Wherever you get your podcasts.
1:30
Jordan
If this is useful, subscribe. We do this every morning.
1:33
Alex
Story one. Start with the thing Anthropic would not sign.
1:38
Jordan
Which was what, exactly?
1:41
Alex
One clause. Any lawful use. The government picks the job, the model does it. Anthropic said no and named two lines. No mass surveillance of Americans. No weapon that picks a target and fires with no person deciding.
1:55
Jordan
That is on the Verge page. Illegally blacklisted, and under it, First Amendment retaliation.
2:02
Alex
Other AI companies signed that same government contract without those two lines in it. Anthropic argued about theirs, loudly, in the press.
2:10
Jordan
So they said no in public, and then...
2:13
Alex
Then the Pentagon called them a supply chain risk. Some of this coverage says Department of War. Same building. That label usually means a vendor who might be compromised. A back door, a foreign owner, a bad part. Hegseth, the defense secretary, told defense contractors to drop them too. Trump posted, immediately cease all use.
2:32
Jordan
Supply chain risk. Over a paragraph in a contract.
2:36
Alex
Judge Rita Lin, federal court in California, ruled yesterday. Fifty nine pages. She threw the whole pile out. Retaliation for speech, and no fair process.
2:46
Jordan
And her line?
2:48
Alex
The empty invocation of national security is not a blank check to punish and retaliate against government critics. She also had the department's own records, complaining Anthropic argued in a hostile manner through the press.
3:02
Jordan
So the paperwork says the offense was talking.
3:06
Alex
Now the part the headlines skip. Further down this CNBC piece. California threw out this pile of orders. A second case, in Washington, is still open, so the risk label is still technically on the books.
3:19
Jordan
They won and they are still on the list?
3:22
Alex
One court, one stack of paper. And nothing here makes the Pentagon buy Claude. That work already went to other companies.
3:30
Jordan
Here is the part nobody leads with. The label did its job before any judge saw it. Contracts gone, agencies switched off, contractors warned away. You cannot un-cancel a year.
3:43
Alex
And I would not have signed that form. If a vendor argues with me in public, I take it up through the contract. I do not write national security on the complaint to win.
3:52
Jordan
Because then somebody else acts on your complaint.
3:56
Alex
All year. Then a judge says it was never true.
4:01
Jordan
I'm on the Hacker News thread. Programmers arguing, not a scoreboard. A hundred and eleven comments. They land on one thing. They knew they would lose and did it anyway, because hurting the vendor was the point.
4:13
Alex
One honest doubt in there too. The post took a second. The court took months.
4:19
Jordan
And Anthropic still says it wants to work with the government on national security.
4:24
Alex
The vendor is still applying.
4:29
Jordan
Story two. On Wednesday Meta settled with fifty two state attorneys general. Their case was that Meta's apps hurt teenagers.
4:38
Alex
Say the real number.
4:40
Jordan
Techdirt read the judgment. The cap written in the document is sixteen point six eight billion dollars, paid across ten years. Meta's own release rounds that to approximately eighteen billion.
4:51
Alex
Ten years. So it is a payment plan with a headline on top.
4:57
Jordan
And it splits in two. About twelve point seven billion pays no matter what. About five point three billion only pays if two other companies do something first.
5:08
Alex
Wait. Meta's payment depends on YouTube and TikTok?
5:13
Alex
Run that again, slower.
5:16
Jordan
YouTube and TikTok each have to add a one hour daily limit, a night mode, and age checks. And each of them has to pay a matching amount. Then Meta owes the last thirty percent. Meta's job in the deal is to push them into it.
5:29
Alex
Okay. That changes how I read this. Meta is not paying a fine. Meta is paying to make its competitors ship Meta's settings.
5:39
Jordan
And if the big apps all end up looking the same, Meta's settings become the industry default.
5:46
Alex
One hour for them. Two hours is the default on Meta's own apps.
5:51
Jordan
But that is not the buried part. TechCrunch read the same agreement.
5:57
Alex
Their headline. Buried in Meta's eighteen billion dollar settlement is a legal pass on kids' data.
6:04
Jordan
This clause here. The states agree, fully, finally, and forever, that they will not bring child privacy claims about how Meta uses children's data to build its age checking system. That system is due within a year.
6:18
Alex
Forever is a strong word to hand a company.
6:22
Jordan
And think about what an age check actually is. To guess that a user is twelve, you gather more about them, not less. The face, the typing, who they talk to.
6:32
Alex
So the fix for collecting too much data on children is...
6:37
Jordan
A system that collects more data on children. Yes.
6:41
Alex
Right.
6:44
Jordan
My cousin Leo is eleven. He lives on a tablet. A bedtime setting would genuinely help him. I still cannot call this a win, because the same deal closes the data question on the thing that scans his face.
6:59
Alex
And the Federal Trade Commission never signed this. The states gave that up, not the federal regulator. Meta still cannot use under thirteen data for ads.
7:08
Jordan
Smaller thread on Hacker News. Best line in it is that the vampire now runs the blood bank.
7:15
Alex
With a fair pushback underneath. A deal only binds the people who signed it. TikTok and YouTube agreed to nothing.
7:22
Jordan
Right. They just got homework. From Meta.
7:26
Alex
Story three. On Wednesday, Treasury and the State Department put a group called Autistici Inventati on the terrorism list.
7:34
Jordan
Who are they?
7:37
Alex
Italian volunteers. Started two thousand one. Free email, free web hosting, chat. No ads, no fees, donations only. They keep almost nothing about their users.
7:48
Jordan
So a small nonprofit inbox.
7:52
Alex
And as of Wednesday, the U.S. calls them a global terrorist group. Same sanctions list the country has used since two thousand one. Listed the same day as a British protest group and a Palestinian network.
8:04
Alex
Treasury's own page. Treasury takes action against violent far left terrorist networks.
8:10
Jordan
What do they say Autistici did?
8:14
Alex
Read the paragraph. They provided encrypted email accounts and hosting to what Treasury calls antifa cells, and by name, the PKK. The Kurdish group the U.S. lists as a terror organization.
8:26
Jordan
Provided as in built them something, or provided as in somebody signed up?
8:31
Alex
Signed up. The State Department's version, through Reason, is that one hosted user published statements for Hamas, Hezbollah and a few others.
8:40
Jordan
One user. On a free email service.
8:43
Jordan
Here is the part nobody leads with. The accusation is the product. Their whole reason to exist is mail and hosting nobody outside can read. That is now the evidence.
8:54
Alex
Reason's line under the headline. The State Department does not accuse them of much more than untraceable email.
9:02
Jordan
And the Electronic Frontier Foundation said it out loud. Jillian York there called it scary. You get listed because the government cannot see inside your service.
9:14
Alex
Then the practical piece. Americans generally cannot do business with a listed group. So a donation is illegal. One dollar. A server bill.
9:24
Jordan
So can you even open the inbox?
9:27
Alex
Their lawyers think reading your own mail, with no money moving, might be allowed. A sanctions lawyer at Georgetown, Peter Harrell, says nobody has tested that in court.
9:37
Jordan
So the people who ran this for twenty five years, and everyone who used it...
9:43
Alex
Do not know what they are allowed to do today.
9:46
Alex
Their homepage, right now. A banner across the top. U.S. sanctions against the A slash I collective. A slash I is them. Autistici Inventati.
9:57
Jordan
They deny the allegations and say they will not back down.
10:01
Alex
No charge. No trial. A press release, and the mail is radioactive.
10:07
Jordan
Thin thread on Hacker News, and the loudest complaint in it is about process. The accuser is also the judge.
10:15
Alex
This was a post-nine-eleven order for money moving to armed groups. It just got used on a hosting policy.
10:23
Alex
One quick one. Top of Hacker News. Stripe said to abandon fifty billion dollar pursuit of PayPal.
10:31
Jordan
Stripe is the plumbing behind a lot of checkout buttons. PayPal is the wallet your parents actually have.
10:38
Alex
Right. In July, Stripe and an investment firm called Advent offered sixty dollars fifty a share. That valued PayPal above fifty three billion. The fifty billion in the headline is the bank loan lined up behind that bid.
10:53
Jordan
So the price and the headline are two different numbers. One is what PayPal is worth at that offer, one is the borrowing.
11:01
Alex
Yes. And Bloomberg's whole story is people familiar with the matter. No name, no filing, no comment from Stripe, Advent or PayPal.
11:11
Jordan
The recaps already say walk away, like somebody signed something. PayPal's board did say the price was too low back in July. That part is on the record.
11:21
Alex
So here is what we know. Somebody told a reporter it is over.
11:26
Jordan
A deal dying quietly still moves real money. It just does not come with a document.
11:33
Alex
So today. A judge in California threw out the Pentagon's orders against Anthropic for refusing an any lawful use clause, and a second case in Washington keeps that supply chain risk label technically alive. Meta's eighteen billion dollar settlement is sixteen point six eight billion over ten years, with a third of it riding on YouTube and TikTok copying Meta's settings, and a forever release on how Meta uses kids' data to guess their ages. Treasury put a twenty five year old Italian volunteer email service on the terrorism list for running email the government cannot read. And somebody told Bloomberg the PayPal bid is dead.
12:07
Jordan
The email one is the one I keep chewing on. No charge, no court date, and a volunteer inbox is now a sanctions problem.
12:17
Alex
That's our audit for today. Find us wherever you get your podcasts. Chief Skeptic Officer, every day at seven A.M. New York time.
12:24
Jordan
Tell us what you're skeptical about. Drop it in the comments. The angle you can't stop chewing on.
12:30
Alex
Stay curious. Stay skeptical.
12:33
Jordan
Doubt both.
