WEBVTT

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Welcome back to the Deep Dive. It is Monday,

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February 23rd, 2026. And I have to say, if you

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were waking up today feeling just a little bit

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of whiplash from the news cycle this weekend,

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you were definitely not alone. It has been a

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lot. A lot is an understatement. Volatile doesn't

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even quite cover it. I mean, we are looking at

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a collision between the executive branch and

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the Supreme Court that we haven't seen in decades.

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Plus a State of the Union address looming tomorrow

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under a very dark cloud and some really fascinating

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shifts in political alliances that I don't think

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anyone had on their bingo card for 2026. No,

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definitely not. And our mission today is to really

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cut through that noise. We aren't just reading

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headlines here. We want to understand the actual

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mechanics of what just happened with the trade

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laws last week because it gets technical, sure,

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but it really matters for your wallet. Right.

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We also need to unpack why a specific group of

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moms who, by the way, were some of the president's

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biggest supporters, is suddenly furious at the

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White House. And we need to figure out why American

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Express is suddenly part of a congressional conversation

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about Jeffrey Epstein. It's a heavy stack of

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sources today. We've got legal analysis of a

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massive 6 -3 Supreme Court decision, reporting

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on the preparations for tomorrow's address, updates

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on the MHA movement that's Make America Healthy

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Again, and some concerning geopolitical maps

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regarding Iran. In a 6 -3 decision, the court

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struck down President Trump's use of the International

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Emergency Economic Powers Act. Right, IE EPA.

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Yeah, IE EPA. They struck down his use of it

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to impose indiscriminate tariffs. Now, for the

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listener who isn't a constitutional scholar,

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how big of a deal is this, actually? It is seismic.

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You really have to understand, IEPA was essentially

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the president's magic sharpie for trade wars.

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Magic sharpie? Yeah, it was the tool in the toolbox

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that allowed the executive branch to bypass Congress

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entirely and just levy taxes on imports under

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the guise of a national emergency. Losing that

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is a massive blow to the administration's operating

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style. It removes the ability to just wake up

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and decide to change the economic landscape.

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But what jumped out at me in the sources wasn't

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just that they lost it. But how they lost it,

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it seemed incredibly specific, like middle school

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English teacher specific. It was a grammar lesson,

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a very high stakes grammar lesson. Chief Justice

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Roberts wrote the opinion and he really drilled

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down into statutory interpretation. He focused

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on just two specific words found in the IEPA

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statute. Regulate. and importation. Just those

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two. Just those two words. Roberts argued that

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these words, which, by the way, are separated

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by 16 other words in the text of the law, they

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simply cannot bear the weight of the president's

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assertion. Because Trump was arguing he had the

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independent power to tax imports from any country.

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Right. Any country at any rate for any amount

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of time based solely on those two words. Essentially,

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the court is saying you are reading way too much

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into this one sentence. Exactly. Robbers actually

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called the assertion of power extravagant by

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any measure and the consequences astonishing.

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And we have to remember the constitutional context

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here. Article 1, Section 8. That's the power

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of the purse. Right. The Constitution explicitly

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gives the power to tax and set tariffs to Congress,

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not the president. The logic was that while IEPA

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gives the president tools for emergencies, like,

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say, freezing assets or stopping trade with a

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specific enemy, levying entirely new taxes across

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the board, just isn't one of them unless Congress

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explicitly says so. Now, there was a subplot

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in the legal analysis that seemed to get the

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legal nerds really excited. Something about the

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major questions doctrine. This feels like inside

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baseball, but... The sources made it seem really

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important. Can you break that down? This is fascinating.

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And it's where the politics of the court get

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really interesting. So the major questions doctrine

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is a legal theory the court has used recently.

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Think back to when they struck down student loan

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forgiveness or the OSHA vaccine mandates. Right,

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I remember that. It's basically the court saying,

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if a government agency wants to do something

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with, he tried. He wanted to use this case to

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cement that doctrine further. But. And this is

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the surprise. He didn't get the votes for that

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specific reasoning. Justices Gorsuch and Barrett

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joined him. But the three liberal justices, Kagan,

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Sotomayor, and Jackson, refused. Wait, so the

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liberals agreed that Trump broke the law, but

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they didn't agree on why? Precisely. They concurred

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on the statutory grounds, the grammar part. But

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they completely refused to sign on to an opinion

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that validated the major questions doctrine.

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They didn't want to hand the conservative wing

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a sharper weapon to use against future regulations,

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say, on the environment or health care. That

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is incredibly strategic. Very. So Trump lost.

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But Roberts didn't get to expand his legal theory

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as much as he wanted to. It was a very calculated

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move by the liberal bloc. Talk about 40 chess.

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And speaking of the reaction, I assume the president

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didn't take this well. He did not. Reports indicate

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he lashed out immediately, specifically calling

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his own appointees, Justices Gorsuch and Barrett,

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disloyal. He even claimed the court had been

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corrupted by foreign influences. Is there any

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evidence for that in the sources? None whatsoever.

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But here's the thing about that whiplash we mentioned

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at the start. He didn't just accept the ruling

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and move on. He pivoted. Right. The sources mentioned

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a different law, Section 122. Yes. The magic

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Sharpie of IEPA might be gone, but the toolbox

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isn't totally empty. Trump immediately pivoted

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to Section 122 of the Trade Act of 1974. He used

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that to impose a new global tariff. First 10%,

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then he upped it to 15 % during a moment of frustration.

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So we are basically back to square one, the tariffs

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are back. Yes and no. This is the gotcha, and

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it's why the next few months are going to be

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crazy. Section 122 has a ticking clock attached

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to it. It requires congressional approval if

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the tariffs last longer than 150 days. 150 days.

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Checking the calendar, that puts us right in

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the middle of summer. Correct. And more importantly,

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right in the heat of primary season. So the Supreme

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Court just forced a future battle between the

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president and Congress. The Republicans in Congress

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are essentially letting him have his 150 days

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now because they don't want to fight him today.

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But come summer. Come summer, they will have

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to decide. Do they vote to keep these tariffs,

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which are economically unpopular and raise prices

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for you and me? Or do they vote against them

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and risk the wrath of the president right before

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an election? That sets up an incredibly dramatic

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summer. But let's look at the immediate future.

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Tomorrow, Tuesday, February 24th, is the State

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of the Union. And the context honestly couldn't

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be much worse for the White House. Approval ratings

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are down, the economy is weakening, and he literally

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just lost that primary tariff authority we discussed.

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A bit of a war going on inside the West Wing

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regarding what he should actually say tomorrow.

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There are two very distinct strategies at play

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here. On one side, you have advisors like Suzy

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Wiles. They want him to play it safe, talk about

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401Ks, claim victory on inflation, try to sound

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steady, basically ignore the chaos and act presidential.

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And the other side? The other side is being described

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as the president's id. They want him to rail

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against the Supreme Court, complain about fake

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news and go completely off script. They want

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the rally speech, not the State of the Union.

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And we all know which one makes for better TV,

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but maybe not better governance. But what really

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caught my eye about tomorrow isn't just the speech

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itself, it's the audience, specifically the guest

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list. The Democrats seem to be coordinating a

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very specific message with who they are inviting

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to sit up in the gallery. It is highly coordinated.

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Senate Majority Leader Chuck Schumer is bringing

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Donnie Bensky. Representative Ro Khanna is bringing

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Haley Robson. For listeners who don't immediately

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recognize those names. Both are victims of Jeffrey

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Epstein. Representative Thomas Massey actually

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estimates that there will be 10 to 12 Epstein

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victims present in the gallery tomorrow. It is

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explicitly designed to keep that shadow over

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the administration and the political class in

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general. It basically forces the cameras to pan

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to them. And this connects to some new, really

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disturbing information in our sources about Epstein

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and a major credit card company. I have to admit,

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seeing American Express in this context was a

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shock. It is a revelation that really shows the

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actual mechanics of how that trafficking operation

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worked. The sources reveal that American Express

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Travel Services booked hundreds of flights for

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women and girls from Eastern Europe. Places like

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Russia, Poland, Latvia, booked them right to

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Epstein's properties. And this wasn't back in

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the 90s. This was recent. Between 2012 and 2019,

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that is long after Epstein was a known convicted

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sex offender. He was already on the registry.

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That is the part I just don't get. How does a

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major corporation one that flags my card if I

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buy coffee in a different city just process hundreds

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of flights for young women to a sex offender's

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island without flagging it. The detail that explains

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it is the specific card he used. Epstein had

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the Amex Centurion card. The black card. Right.

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Invite only $10 ,000 initiation fee. The implication

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in the reporting is that when you are at that

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level of spending, the scrutiny just disappears.

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The compliance algorithms that watch regular

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people just don't apply to the ultra wealthy.

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It bypassed the usual red flags simply because

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he was a whale. Congress going after AMEX, or

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are we going to see the CEO testifying? House

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Oversight Chairman James Comer is taking a different

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angle and sources suggest it might backfire.

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He's focusing on subpoenaing Bill and Hillary

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Clinton rather than hauling in the AMEX executives.

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Which seems like a huge political risk. It is.

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The Clintons have a history of being incredibly

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resilient during testimony. Remember, Bill Clinton's

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popularity actually went up during his impeachment

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proceedings. Focusing on them instead of the

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corporate enablers at American Express might

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look like political theater rather than a genuine

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invention. investigation into the trafficking

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network. Because it allows the company to slide

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out the back door while the politicians fight

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on stage. Exactly. Okay, let's shift gears to

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another headache for the administration. And

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this one is coming from inside the house, so

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to speak. The MAHA movement. Make America healthy

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again. Right. This was that coalition brought

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in by Robert F. Kennedy Jr. Mom's concerned about

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food safety, chemicals, chronic disease. They

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were a key part of the voting block. But now,

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the sources say they are absolutely furious.

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They feel completely betrayed. And it centers

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on one specific chemical. Glyphosate. That's

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the active ingredient around them. The weed killer.

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It is. It's the most used weed killer in history.

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We're talking... 300 million pounds a year on

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US crops. The MAHA supporters view it as neurotoxic

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and carcinogenic. They genuinely thought this

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administration would ban it or at least heavily

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reduce it. That was the implied promise. And

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instead, the president did the exact opposite.

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He signed an executive order invoking the Defense

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Production Act to actually spur the production

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of glyphosate. Wait, let's just pause on that

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for a second. He used the Defense Production

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Act, which is usually for wartime supplies like

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steel or masks, to make more weed killer. Yes.

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The justification is twofold. One, to keep food

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costs down for farmers because Roundup ready

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crops are cheaper to grow. But the other reason,

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and this is the official cover story according

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to the sources, is that they need the phosphorus.

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Phosphorus. Phosphorus is a key component of

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glyphosate, but it's also highly used in munitions.

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So the trade -off is cheap food and ammo. Exactly.

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But try explaining that to Alex Clark from Turning

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Point USA or Vani Hari, known as the Food Babe.

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These are really influential figures in that

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movement who rallied voters for Trump. Alex Clark

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was actually quoted asking, how can we win their

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trust back? It seems like a massive unforced

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error to alienate such a passionate slice of

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your coalition right before the midterms. It

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is. And it really shows the friction between

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the populist health wing of the party and the

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industrial military wing. They are on a collision

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course. You can't really have a healthy living

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movement and a maximized chemical production

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movement in the exact same tent without things

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getting incredibly messy. And speaking of military

00:12:05.860 --> 00:12:07.480
collisions, we need to look at the map for a

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minute. While we are arguing about weed killer

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domestically, warships are moving in the Middle

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East. Yes. The USS Gerald R. Ford and its strike

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group are heading toward Iran. The sources actually

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call this a game of chicken. It's a high -stakes

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one. Negotiations on nuclear development have

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totally stalled. The military assets are expected

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to be in place by mid -March. But the real threat

00:12:28.620 --> 00:12:31.519
here isn't necessarily a ground invasion or a

00:12:31.519 --> 00:12:35.120
nuclear strike. It's the geography. The Strait

00:12:35.120 --> 00:12:38.559
of Hormuz. Precisely. If you visualize the map,

00:12:38.750 --> 00:12:42.049
The Persian Gulf narrows down to this tiny choke

00:12:42.049 --> 00:12:45.070
point. The navigable channel for large ships

00:12:45.070 --> 00:12:48.509
is only two miles wide. Two miles. That is absolutely

00:12:48.509 --> 00:12:51.850
nothing in naval terms. It's tiny. But one fifth

00:12:51.850 --> 00:12:54.190
of the world's oil and liquefied natural gas

00:12:54.190 --> 00:12:57.070
passes right through that two mile strip. So

00:12:57.070 --> 00:12:59.370
Iran doesn't actually have to win a war against

00:12:59.370 --> 00:13:01.149
the U .S. Navy. They just have to mess up that

00:13:01.149 --> 00:13:04.029
channel. Correct. Iran's strategy, according

00:13:04.029 --> 00:13:06.389
to our analysis, isn't to win a shooting war.

00:13:06.549 --> 00:13:08.429
It's to threaten to sink tankers in that channel.

00:13:08.690 --> 00:13:10.730
If they do that, or even just credibly threaten

00:13:10.730 --> 00:13:13.450
it, insurance rates for shipping companies skyrocket.

00:13:13.710 --> 00:13:15.690
Right, because if Lloyds of London won't insure

00:13:15.690 --> 00:13:18.149
the ship, the ship simply doesn't sail. Exactly.

00:13:18.330 --> 00:13:20.610
Shipping stops entirely. Oil prices go through

00:13:20.610 --> 00:13:23.470
the roof. And if gas hits $7 or $8 a gallon here

00:13:23.470 --> 00:13:26.799
at home? The global economy spirals and the administration

00:13:26.799 --> 00:13:29.919
is doomed politically. That kind of economic

00:13:29.919 --> 00:13:33.000
chaos is the real weapon. It's asymmetric warfare.

00:13:33.379 --> 00:13:34.940
You don't need to sink the aircraft carrier.

00:13:35.279 --> 00:13:37.220
You just need to make the insurance premiums

00:13:37.220 --> 00:13:40.299
too high for the oil tankers to sail. And that

00:13:40.299 --> 00:13:43.759
reality serves as a massive check on the administration's

00:13:43.759 --> 00:13:46.740
ability to act aggressively. So we have the Supreme

00:13:46.740 --> 00:13:49.700
Court checking the president on trade, a fractured

00:13:49.700 --> 00:13:53.740
base with the MAHA moms, and a potential economic

00:13:53.740 --> 00:13:56.759
disaster brewing in this trade of Hormuz. Let's

00:13:56.759 --> 00:13:59.340
bring it back to the ballot box because the political

00:13:59.340 --> 00:14:01.100
maneuvering for the midterms and even looking

00:14:01.100 --> 00:14:04.539
ahead to 2028 is already getting weird. Weird

00:14:04.539 --> 00:14:06.779
is a good word for it. Let's look at Colorado's

00:14:06.779 --> 00:14:08.820
third district. This is a perfect example of

00:14:08.820 --> 00:14:11.220
down -ballot chaos. This is the seat held by

00:14:11.220 --> 00:14:13.980
Republican Jeff Hurd. Jeff Hurd is a fairly standard

00:14:13.980 --> 00:14:16.419
Republican who voted against the tariffs on Canada.

00:14:16.740 --> 00:14:19.220
Why? Because his district relies on trade with

00:14:19.220 --> 00:14:22.220
Canada. He was voting for his constituents' wallets.

00:14:22.379 --> 00:14:24.889
And Trump didn't like that. Trump de -endorsed

00:14:24.889 --> 00:14:27.929
him, and he endorsed a candidate named Hope Shepleman

00:14:27.929 --> 00:14:31.090
instead. Sources describe her as an extremist,

00:14:31.370 --> 00:14:33.769
so much so that she's actually been removed from

00:14:33.769 --> 00:14:36.769
party leadership positions before. And this infighting

00:14:36.769 --> 00:14:39.610
creates an opening. A massive opening. Sources

00:14:39.610 --> 00:14:42.460
suggest this seat which should be safe Republican,

00:14:42.720 --> 00:14:45.740
is now totally in play. The Democrats have a

00:14:45.740 --> 00:14:48.440
candidate named Kyle Doster, who is a barista.

00:14:48.580 --> 00:14:50.879
A barista, like pulling espresso shots. Yes.

00:14:50.879 --> 00:14:52.860
And I don't mean that as a slight at all. It's

00:14:52.860 --> 00:14:55.620
just a stark contrast to a seasoned politician.

00:14:55.940 --> 00:14:58.419
But because the Republican vote is potentially

00:14:58.419 --> 00:15:01.600
going to be split or depressed by a radical candidate,

00:15:02.120 --> 00:15:04.659
a barista might actually end up in Congress.

00:15:04.879 --> 00:15:07.539
It really illustrates how the purity tests from

00:15:07.539 --> 00:15:09.320
the top of the ticket can cost the party seats

00:15:09.320 --> 00:15:11.610
that should be easy win. And then there is Texas.

00:15:12.190 --> 00:15:14.210
The money being spent there is eye -watering.

00:15:14.350 --> 00:15:17.009
It is the Senate race. Incumbent John Cornyn

00:15:17.009 --> 00:15:19.830
versus Attorney General Ken Paxton. The establishment

00:15:19.830 --> 00:15:22.830
is terrified of Paxton winning the primary. They

00:15:22.830 --> 00:15:25.210
have already spent over 90 million dollars to

00:15:25.210 --> 00:15:28.210
save Cornyn. 90 million? That seems like an insane

00:15:28.210 --> 00:15:30.889
amount of money for just a primary. And that's

00:15:30.889 --> 00:15:34.149
before the runoff. It's dark money, oil money.

00:15:34.919 --> 00:15:37.659
They are flooding the zone because they know

00:15:37.659 --> 00:15:40.639
if Paxton wins the primary, the seat becomes

00:15:40.639 --> 00:15:43.460
vulnerable in the general election. They are

00:15:43.460 --> 00:15:45.960
paying an absolute fortune to keep Maggie Gay

00:15:45.960 --> 00:15:48.559
candidates off the general election ballot just

00:15:48.559 --> 00:15:52.139
to save the Senate majority. It's basically a

00:15:52.139 --> 00:15:55.320
civil war within the party, fought with ad buys.

00:15:55.779 --> 00:15:57.259
Before we wrap up, we have to touch on the list

00:15:57.259 --> 00:15:59.360
that everyone in the political nerd sphere is

00:15:59.360 --> 00:16:01.899
talking about right now. Nate Silver released

00:16:01.899 --> 00:16:04.179
his rankings for the twenty twenty eight Democratic

00:16:04.200 --> 00:16:08.080
Ah, yes, the list. You sound skeptical. Well,

00:16:08.220 --> 00:16:10.080
the sources are skeptical. Nate Silver has people

00:16:10.080 --> 00:16:12.779
like Gavin Newsom, AOC, and Pete Buttigieg right

00:16:12.779 --> 00:16:14.460
at the top. Which makes sense. On paper, they

00:16:14.460 --> 00:16:16.419
are the most famous. They completely dominate

00:16:16.419 --> 00:16:18.840
the Twitter feed. They are famous. But the critique

00:16:18.840 --> 00:16:21.700
here is that Silver is confusing hype with electability,

00:16:22.259 --> 00:16:24.480
especially with white working class voters in

00:16:24.480 --> 00:16:27.519
swing states. The internet is not the electorate.

00:16:27.840 --> 00:16:29.960
So who does the analysis suggest we should actually

00:16:29.960 --> 00:16:32.580
be watching? The sources suggest looking at governors

00:16:32.580 --> 00:16:35.740
like Josh Shapiro in Pennsylvania or Andy Beshear

00:16:35.740 --> 00:16:37.990
in Kentucky. The guys who actually win in red

00:16:37.990 --> 00:16:40.870
or purple states. Exactly. They aren't generating

00:16:40.870 --> 00:16:44.549
the same internet buzz as AOC, but statistically

00:16:44.549 --> 00:16:46.850
they are much safer bets to actually win the

00:16:46.850 --> 00:16:49.269
electoral college. The argument is that silver

00:16:49.269 --> 00:16:51.690
is looking at who excites the activist base,

00:16:51.850 --> 00:16:53.990
not who actually wins the general election in

00:16:53.990 --> 00:16:55.889
places like Wisconsin or Michigan. It's always

00:16:55.889 --> 00:16:58.409
the quiet ones you have to watch. Always. So

00:16:58.409 --> 00:17:00.029
let's bring this all together. We've covered

00:17:00.029 --> 00:17:02.970
a lot of ground today from Robert's grammar lesson

00:17:02.970 --> 00:17:07.450
to Iranian tankers to Colorado. East is. What

00:17:07.450 --> 00:17:09.769
is the through line here for the listener? I

00:17:09.769 --> 00:17:11.730
think the real theme of this deep dive is that

00:17:11.730 --> 00:17:13.970
the checks and checks and balances are hitting

00:17:13.970 --> 00:17:16.109
back hard. You have the Supreme Court drawing

00:17:16.109 --> 00:17:19.390
a red line on tariffs. You have political coalitions

00:17:19.390 --> 00:17:22.369
like the MAHA movement fracturing because promises

00:17:22.369 --> 00:17:25.029
simply weren't kept. And you have the economic

00:17:25.029 --> 00:17:27.650
reality of the Strait of Hormuz checking military

00:17:27.650 --> 00:17:30.230
ambition. Feels like gravity is reasserting itself.

00:17:30.559 --> 00:17:32.440
That's a really great way to put it. You can

00:17:32.440 --> 00:17:34.920
only defy political and economic gravity for

00:17:34.920 --> 00:17:38.019
so long before the mechanics of the system, the

00:17:38.019 --> 00:17:40.099
laws, the supply chains, the voters start to

00:17:40.099 --> 00:17:41.880
push back. I want to leave the listener with

00:17:41.880 --> 00:17:44.160
one final thought, something to really chew on

00:17:44.160 --> 00:17:46.299
based on what we've learned. You mentioned earlier

00:17:46.299 --> 00:17:50.200
that 150 -day clock on the new Section 122 Terrace.

00:17:50.400 --> 00:17:52.940
Yes. That is the thing I honestly can't stop

00:17:52.940 --> 00:17:54.779
thinking about. If you look at the calendar,

00:17:55.619 --> 00:17:58.000
150 days from now lands us right in the summer

00:17:58.000 --> 00:18:02.200
of 2026. So what happens then? That is the multi

00:18:02.200 --> 00:18:04.579
-billion dollar question. When that clock runs

00:18:04.579 --> 00:18:07.180
out, Republicans in Congress will have to make

00:18:07.180 --> 00:18:10.039
a binary choice. Do they block the tariffs to

00:18:10.039 --> 00:18:12.519
save the economy and lower prices for their voters?

00:18:12.960 --> 00:18:15.680
Or do they fold and let the tariffs stand just

00:18:15.680 --> 00:18:18.039
to avoid a primary challenge from the president?

00:18:18.779 --> 00:18:20.660
The timeline suggests we are heading straight

00:18:20.660 --> 00:18:23.359
for a summer of economic brinksmanship that will

00:18:23.359 --> 00:18:25.720
decide the fate of the midterms. It's a game

00:18:25.720 --> 00:18:28.619
of chicken and the cars are speeding up. A ticking

00:18:28.619 --> 00:18:30.460
clock right in the middle of an election year.

00:18:30.680 --> 00:18:32.380
We will definitely be watching that closely.

00:18:32.900 --> 00:18:34.559
That's it for this deep dive. Thanks so much

00:18:34.559 --> 00:18:35.700
for listening. See you next time.
