Welcome back to the Deep Dive. It is Monday,
February 23rd, 2026. And I have to say, if you
were waking up today feeling just a little bit
of whiplash from the news cycle this weekend,
you were definitely not alone. It has been a
lot. A lot is an understatement. Volatile doesn't
even quite cover it. I mean, we are looking at
a collision between the executive branch and
the Supreme Court that we haven't seen in decades.
Plus a State of the Union address looming tomorrow
under a very dark cloud and some really fascinating
shifts in political alliances that I don't think
anyone had on their bingo card for 2026. No,
definitely not. And our mission today is to really
cut through that noise. We aren't just reading
headlines here. We want to understand the actual
mechanics of what just happened with the trade
laws last week because it gets technical, sure,
but it really matters for your wallet. Right.
We also need to unpack why a specific group of
moms who, by the way, were some of the president's
biggest supporters, is suddenly furious at the
White House. And we need to figure out why American
Express is suddenly part of a congressional conversation
about Jeffrey Epstein. It's a heavy stack of
sources today. We've got legal analysis of a
massive 6 -3 Supreme Court decision, reporting
on the preparations for tomorrow's address, updates
on the MHA movement that's Make America Healthy
Again, and some concerning geopolitical maps
regarding Iran. In a 6 -3 decision, the court
struck down President Trump's use of the International
Emergency Economic Powers Act. Right, IE EPA.
Yeah, IE EPA. They struck down his use of it
to impose indiscriminate tariffs. Now, for the
listener who isn't a constitutional scholar,
how big of a deal is this, actually? It is seismic.
You really have to understand, IEPA was essentially
the president's magic sharpie for trade wars.
Magic sharpie? Yeah, it was the tool in the toolbox
that allowed the executive branch to bypass Congress
entirely and just levy taxes on imports under
the guise of a national emergency. Losing that
is a massive blow to the administration's operating
style. It removes the ability to just wake up
and decide to change the economic landscape.
But what jumped out at me in the sources wasn't
just that they lost it. But how they lost it,
it seemed incredibly specific, like middle school
English teacher specific. It was a grammar lesson,
a very high stakes grammar lesson. Chief Justice
Roberts wrote the opinion and he really drilled
down into statutory interpretation. He focused
on just two specific words found in the IEPA
statute. Regulate. and importation. Just those
two. Just those two words. Roberts argued that
these words, which, by the way, are separated
by 16 other words in the text of the law, they
simply cannot bear the weight of the president's
assertion. Because Trump was arguing he had the
independent power to tax imports from any country.
Right. Any country at any rate for any amount
of time based solely on those two words. Essentially,
the court is saying you are reading way too much
into this one sentence. Exactly. Robbers actually
called the assertion of power extravagant by
any measure and the consequences astonishing.
And we have to remember the constitutional context
here. Article 1, Section 8. That's the power
of the purse. Right. The Constitution explicitly
gives the power to tax and set tariffs to Congress,
not the president. The logic was that while IEPA
gives the president tools for emergencies, like,
say, freezing assets or stopping trade with a
specific enemy, levying entirely new taxes across
the board, just isn't one of them unless Congress
explicitly says so. Now, there was a subplot
in the legal analysis that seemed to get the
legal nerds really excited. Something about the
major questions doctrine. This feels like inside
baseball, but... The sources made it seem really
important. Can you break that down? This is fascinating.
And it's where the politics of the court get
really interesting. So the major questions doctrine
is a legal theory the court has used recently.
Think back to when they struck down student loan
forgiveness or the OSHA vaccine mandates. Right,
I remember that. It's basically the court saying,
if a government agency wants to do something
with, he tried. He wanted to use this case to
cement that doctrine further. But. And this is
the surprise. He didn't get the votes for that
specific reasoning. Justices Gorsuch and Barrett
joined him. But the three liberal justices, Kagan,
Sotomayor, and Jackson, refused. Wait, so the
liberals agreed that Trump broke the law, but
they didn't agree on why? Precisely. They concurred
on the statutory grounds, the grammar part. But
they completely refused to sign on to an opinion
that validated the major questions doctrine.
They didn't want to hand the conservative wing
a sharper weapon to use against future regulations,
say, on the environment or health care. That
is incredibly strategic. Very. So Trump lost.
But Roberts didn't get to expand his legal theory
as much as he wanted to. It was a very calculated
move by the liberal bloc. Talk about 40 chess.
And speaking of the reaction, I assume the president
didn't take this well. He did not. Reports indicate
he lashed out immediately, specifically calling
his own appointees, Justices Gorsuch and Barrett,
disloyal. He even claimed the court had been
corrupted by foreign influences. Is there any
evidence for that in the sources? None whatsoever.
But here's the thing about that whiplash we mentioned
at the start. He didn't just accept the ruling
and move on. He pivoted. Right. The sources mentioned
a different law, Section 122. Yes. The magic
Sharpie of IEPA might be gone, but the toolbox
isn't totally empty. Trump immediately pivoted
to Section 122 of the Trade Act of 1974. He used
that to impose a new global tariff. First 10%,
then he upped it to 15 % during a moment of frustration.
So we are basically back to square one, the tariffs
are back. Yes and no. This is the gotcha, and
it's why the next few months are going to be
crazy. Section 122 has a ticking clock attached
to it. It requires congressional approval if
the tariffs last longer than 150 days. 150 days.
Checking the calendar, that puts us right in
the middle of summer. Correct. And more importantly,
right in the heat of primary season. So the Supreme
Court just forced a future battle between the
president and Congress. The Republicans in Congress
are essentially letting him have his 150 days
now because they don't want to fight him today.
But come summer. Come summer, they will have
to decide. Do they vote to keep these tariffs,
which are economically unpopular and raise prices
for you and me? Or do they vote against them
and risk the wrath of the president right before
an election? That sets up an incredibly dramatic
summer. But let's look at the immediate future.
Tomorrow, Tuesday, February 24th, is the State
of the Union. And the context honestly couldn't
be much worse for the White House. Approval ratings
are down, the economy is weakening, and he literally
just lost that primary tariff authority we discussed.
A bit of a war going on inside the West Wing
regarding what he should actually say tomorrow.
There are two very distinct strategies at play
here. On one side, you have advisors like Suzy
Wiles. They want him to play it safe, talk about
401Ks, claim victory on inflation, try to sound
steady, basically ignore the chaos and act presidential.
And the other side? The other side is being described
as the president's id. They want him to rail
against the Supreme Court, complain about fake
news and go completely off script. They want
the rally speech, not the State of the Union.
And we all know which one makes for better TV,
but maybe not better governance. But what really
caught my eye about tomorrow isn't just the speech
itself, it's the audience, specifically the guest
list. The Democrats seem to be coordinating a
very specific message with who they are inviting
to sit up in the gallery. It is highly coordinated.
Senate Majority Leader Chuck Schumer is bringing
Donnie Bensky. Representative Ro Khanna is bringing
Haley Robson. For listeners who don't immediately
recognize those names. Both are victims of Jeffrey
Epstein. Representative Thomas Massey actually
estimates that there will be 10 to 12 Epstein
victims present in the gallery tomorrow. It is
explicitly designed to keep that shadow over
the administration and the political class in
general. It basically forces the cameras to pan
to them. And this connects to some new, really
disturbing information in our sources about Epstein
and a major credit card company. I have to admit,
seeing American Express in this context was a
shock. It is a revelation that really shows the
actual mechanics of how that trafficking operation
worked. The sources reveal that American Express
Travel Services booked hundreds of flights for
women and girls from Eastern Europe. Places like
Russia, Poland, Latvia, booked them right to
Epstein's properties. And this wasn't back in
the 90s. This was recent. Between 2012 and 2019,
that is long after Epstein was a known convicted
sex offender. He was already on the registry.
That is the part I just don't get. How does a
major corporation one that flags my card if I
buy coffee in a different city just process hundreds
of flights for young women to a sex offender's
island without flagging it. The detail that explains
it is the specific card he used. Epstein had
the Amex Centurion card. The black card. Right.
Invite only $10 ,000 initiation fee. The implication
in the reporting is that when you are at that
level of spending, the scrutiny just disappears.
The compliance algorithms that watch regular
people just don't apply to the ultra wealthy.
It bypassed the usual red flags simply because
he was a whale. Congress going after AMEX, or
are we going to see the CEO testifying? House
Oversight Chairman James Comer is taking a different
angle and sources suggest it might backfire.
He's focusing on subpoenaing Bill and Hillary
Clinton rather than hauling in the AMEX executives.
Which seems like a huge political risk. It is.
The Clintons have a history of being incredibly
resilient during testimony. Remember, Bill Clinton's
popularity actually went up during his impeachment
proceedings. Focusing on them instead of the
corporate enablers at American Express might
look like political theater rather than a genuine
invention. investigation into the trafficking
network. Because it allows the company to slide
out the back door while the politicians fight
on stage. Exactly. Okay, let's shift gears to
another headache for the administration. And
this one is coming from inside the house, so
to speak. The MAHA movement. Make America healthy
again. Right. This was that coalition brought
in by Robert F. Kennedy Jr. Mom's concerned about
food safety, chemicals, chronic disease. They
were a key part of the voting block. But now,
the sources say they are absolutely furious.
They feel completely betrayed. And it centers
on one specific chemical. Glyphosate. That's
the active ingredient around them. The weed killer.
It is. It's the most used weed killer in history.
We're talking... 300 million pounds a year on
US crops. The MAHA supporters view it as neurotoxic
and carcinogenic. They genuinely thought this
administration would ban it or at least heavily
reduce it. That was the implied promise. And
instead, the president did the exact opposite.
He signed an executive order invoking the Defense
Production Act to actually spur the production
of glyphosate. Wait, let's just pause on that
for a second. He used the Defense Production
Act, which is usually for wartime supplies like
steel or masks, to make more weed killer. Yes.
The justification is twofold. One, to keep food
costs down for farmers because Roundup ready
crops are cheaper to grow. But the other reason,
and this is the official cover story according
to the sources, is that they need the phosphorus.
Phosphorus. Phosphorus is a key component of
glyphosate, but it's also highly used in munitions.
So the trade -off is cheap food and ammo. Exactly.
But try explaining that to Alex Clark from Turning
Point USA or Vani Hari, known as the Food Babe.
These are really influential figures in that
movement who rallied voters for Trump. Alex Clark
was actually quoted asking, how can we win their
trust back? It seems like a massive unforced
error to alienate such a passionate slice of
your coalition right before the midterms. It
is. And it really shows the friction between
the populist health wing of the party and the
industrial military wing. They are on a collision
course. You can't really have a healthy living
movement and a maximized chemical production
movement in the exact same tent without things
getting incredibly messy. And speaking of military
collisions, we need to look at the map for a
minute. While we are arguing about weed killer
domestically, warships are moving in the Middle
East. Yes. The USS Gerald R. Ford and its strike
group are heading toward Iran. The sources actually
call this a game of chicken. It's a high -stakes
one. Negotiations on nuclear development have
totally stalled. The military assets are expected
to be in place by mid -March. But the real threat
here isn't necessarily a ground invasion or a
nuclear strike. It's the geography. The Strait
of Hormuz. Precisely. If you visualize the map,
The Persian Gulf narrows down to this tiny choke
point. The navigable channel for large ships
is only two miles wide. Two miles. That is absolutely
nothing in naval terms. It's tiny. But one fifth
of the world's oil and liquefied natural gas
passes right through that two mile strip. So
Iran doesn't actually have to win a war against
the U .S. Navy. They just have to mess up that
channel. Correct. Iran's strategy, according
to our analysis, isn't to win a shooting war.
It's to threaten to sink tankers in that channel.
If they do that, or even just credibly threaten
it, insurance rates for shipping companies skyrocket.
Right, because if Lloyds of London won't insure
the ship, the ship simply doesn't sail. Exactly.
Shipping stops entirely. Oil prices go through
the roof. And if gas hits $7 or $8 a gallon here
at home? The global economy spirals and the administration
is doomed politically. That kind of economic
chaos is the real weapon. It's asymmetric warfare.
You don't need to sink the aircraft carrier.
You just need to make the insurance premiums
too high for the oil tankers to sail. And that
reality serves as a massive check on the administration's
ability to act aggressively. So we have the Supreme
Court checking the president on trade, a fractured
base with the MAHA moms, and a potential economic
disaster brewing in this trade of Hormuz. Let's
bring it back to the ballot box because the political
maneuvering for the midterms and even looking
ahead to 2028 is already getting weird. Weird
is a good word for it. Let's look at Colorado's
third district. This is a perfect example of
down -ballot chaos. This is the seat held by
Republican Jeff Hurd. Jeff Hurd is a fairly standard
Republican who voted against the tariffs on Canada.
Why? Because his district relies on trade with
Canada. He was voting for his constituents' wallets.
And Trump didn't like that. Trump de -endorsed
him, and he endorsed a candidate named Hope Shepleman
instead. Sources describe her as an extremist,
so much so that she's actually been removed from
party leadership positions before. And this infighting
creates an opening. A massive opening. Sources
suggest this seat which should be safe Republican,
is now totally in play. The Democrats have a
candidate named Kyle Doster, who is a barista.
A barista, like pulling espresso shots. Yes.
And I don't mean that as a slight at all. It's
just a stark contrast to a seasoned politician.
But because the Republican vote is potentially
going to be split or depressed by a radical candidate,
a barista might actually end up in Congress.
It really illustrates how the purity tests from
the top of the ticket can cost the party seats
that should be easy win. And then there is Texas.
The money being spent there is eye -watering.
It is the Senate race. Incumbent John Cornyn
versus Attorney General Ken Paxton. The establishment
is terrified of Paxton winning the primary. They
have already spent over 90 million dollars to
save Cornyn. 90 million? That seems like an insane
amount of money for just a primary. And that's
before the runoff. It's dark money, oil money.
They are flooding the zone because they know
if Paxton wins the primary, the seat becomes
vulnerable in the general election. They are
paying an absolute fortune to keep Maggie Gay
candidates off the general election ballot just
to save the Senate majority. It's basically a
civil war within the party, fought with ad buys.
Before we wrap up, we have to touch on the list
that everyone in the political nerd sphere is
talking about right now. Nate Silver released
his rankings for the twenty twenty eight Democratic
Ah, yes, the list. You sound skeptical. Well,
the sources are skeptical. Nate Silver has people
like Gavin Newsom, AOC, and Pete Buttigieg right
at the top. Which makes sense. On paper, they
are the most famous. They completely dominate
the Twitter feed. They are famous. But the critique
here is that Silver is confusing hype with electability,
especially with white working class voters in
swing states. The internet is not the electorate.
So who does the analysis suggest we should actually
be watching? The sources suggest looking at governors
like Josh Shapiro in Pennsylvania or Andy Beshear
in Kentucky. The guys who actually win in red
or purple states. Exactly. They aren't generating
the same internet buzz as AOC, but statistically
they are much safer bets to actually win the
electoral college. The argument is that silver
is looking at who excites the activist base,
not who actually wins the general election in
places like Wisconsin or Michigan. It's always
the quiet ones you have to watch. Always. So
let's bring this all together. We've covered
a lot of ground today from Robert's grammar lesson
to Iranian tankers to Colorado. East is. What
is the through line here for the listener? I
think the real theme of this deep dive is that
the checks and checks and balances are hitting
back hard. You have the Supreme Court drawing
a red line on tariffs. You have political coalitions
like the MAHA movement fracturing because promises
simply weren't kept. And you have the economic
reality of the Strait of Hormuz checking military
ambition. Feels like gravity is reasserting itself.
That's a really great way to put it. You can
only defy political and economic gravity for
so long before the mechanics of the system, the
laws, the supply chains, the voters start to
push back. I want to leave the listener with
one final thought, something to really chew on
based on what we've learned. You mentioned earlier
that 150 -day clock on the new Section 122 Terrace.
Yes. That is the thing I honestly can't stop
thinking about. If you look at the calendar,
150 days from now lands us right in the summer
of 2026. So what happens then? That is the multi
-billion dollar question. When that clock runs
out, Republicans in Congress will have to make
a binary choice. Do they block the tariffs to
save the economy and lower prices for their voters?
Or do they fold and let the tariffs stand just
to avoid a primary challenge from the president?
The timeline suggests we are heading straight
for a summer of economic brinksmanship that will
decide the fate of the midterms. It's a game
of chicken and the cars are speeding up. A ticking
clock right in the middle of an election year.
We will definitely be watching that closely.
That's it for this deep dive. Thanks so much
for listening. See you next time.