Three Chilling Tales from Trump’s Inner Circle They Didn’t Want You to Hear

Inside the moments that had his own staff wondering if the country would survive him.

Three Chilling Tales from Trump’s Inner Circle They Didn’t Want You to Hear

Inside the moments that had his own staff wondering if the country would survive him.

The Jack Hopkins Now Newsletter #489: Thursday, August 14th, 2025.

There’s a beat…when the curtains pull back…when the veil lifts…and you glimpse something dreadful…something undreamt…something that shadows the mind with the sheer force of irrational terror.

Most have heard snippets. “Greenland for sale.” “Wall spikes.” “Gators in ditches.” But behind the scenes…from the mouths of those who lived it…are moments so unhinged… so terrifying in their absurdity…they beg belief.

Here are three stories…straight from the pens and testimonies of those who stood closest to Trump…proof that this wasn’t theater; it was the edge of chaos.

Why am I putting these three stories in front of you? Because one of the oldest human defense mechanisms is to smooth over the bad things and make it sound less ugly than it is. That instinct can prove very dangerous.

I simply want give you three reasons today you can use to interrupt any such rationalization you might be unconsciously (or otherwise) be inclined to engage in.

1. Missiles to Mexico: “No one would know it was us.”

Source:

A Sacred Oath, by Mark Esper (former Secretary of Defense)

What happened:

In the summer of 2020, faced with the border drug crisis, Trump reportedly asked if we could secretly fire missiles into Mexico to take out cartel drug labs. Twice.

In Esper’s words:

“He asked … whether the military could shoot missiles into Mexico to destroy the drug labs.” Vanity FairYouTube+12People.com+12Texas Public Policy Foundation -+12YouTube+14Spectrum Local News+14People.com+14

When Esper pointed out the obvious…international law, ruination of diplomatic relations, global outrage…Trump brushed it aside:

“No one would know it was us.” CBS NewsPeople.com+2Vanity Fair+2

And pushed further:

“We could just shoot some Patriot missiles … quietly,” and when reminded that, of course, they would know it was the U.S., Trump reportedly replied he'd simply lie. DIE WELT+15Vanity Fair+15Newsweek+15

This wasn’t fantasy. Esper…stunned…had to talk him down. After one particularly fraught exchange...Esper realized: I’m writing this down—with witnesses. CBS News

That isn’t paranoia. That’s a national security nightmare: a president ready to wage secret war on a neighbor and lie about it. A man with an unchecked impulse…the disregard for law…the authoritarian edge. If "missile diplomacy" existed…this was it.

2. The “Music Man” and the show-tune sedative

Source:

I’ll Take Your Questions Now, by Stephanie Grisham (former Press Secretary)

What happened:

In the White House…when Trump teetered on the brink of fury…an aide known as the “Music Man”would scramble: he would queue up Memory from Cats, broadcast it directly to the president…and calm him.

Grisham recounts:

A White House aide was tasked with playing Trump his favorite show tunes to calm him down—“Memory” from Cats. DIE WELT+8Business Insider+8TheWrap+8

International audiences were riveted when the German paper Welt headlined:

“Musik-Mann” sollte Trump bei Wutanfällen beruhigen der “Music Man” spielte “Memory” aus dem Musical Cats.” Vanity Fair+7DIE WELT+7Business Insider+7

One excerpt captures the absurd intimacy:

Trump reassured Grisham that his own penis wasn’t small…contradicting porn star Stormy Daniels’s claims…a detail delivered in the context of the Music Man calming sessions. Defense Priorities+10Vanity Fair+10The New Yorker+10

This isn’t just sitcom absurdity. It’s a window into a man infantilized by rage and ego. When a president’s emotions must be medicated by Broadway tunes…when a tantrum is only quelled by Memory…you glimpse a mind untethered.

And when such moments include bizarre personal defenses mid‑crisis…you sense a psychological spiral deeper than public theater.

3. Selling Puerto Rico: “Can we just divest of that asset?”

Source:

Elaine Duke (former Acting Secretary, Department of Homeland Security)

What happened:

In the wake of Hurricane Maria’s devastation (2017), Trump…evaluating Puerto Rico like a business asset…reportedly asked if the U.S. could “sell the island”…or at least “divest” it.

Duke recalls:

Trump’s initial ideas were more of as a businessman … “Can we outsource the electricity? Can we sell the island? Or divest of that asset?” Business Insider+1

She was “shocked.” It was not pursued…but the notion flipped the moral compass: a territory…its people…reduced to a transaction.

Public coverage echoes her astonishment:

“President Donald Trump suggested selling Puerto Rico… ‘divesting’ or ‘selling’ the island.” Business InsiderHSToday+4KSBY News+4Business Insider+4

Here is the pinnacle of absurd detachment: the president not just lacking empathy… but literally advising the abandonment of U.S. citizens…Americans under worst hardship…as if they were bad debt.

Weaving the threads: What does it all reveal?

You’ve read three stories…each divorced from each other in time and department. But thread them together…and a portrait emerges:

• Unmoored moral compass: Threatening a neighboring country with secret war. Treating U.S. territories like business assets.

• Ego beyond measure: A man whose fit of anger required show tunes to soothe… whose self‑image compelled bizarre public assurances about intimate details.

• Unchecked impulsivity: These weren’t hypothetical musings; they were serious inquiries from the Oval Office, landed on rationalists like Esper…and only prevented by their resistance.

These are not caricatures. These are testimonies. These are receipts.

It’s easy to get numb. It’s easy to think you’ve “heard it all” about Donald Trump. But stories like these rip that anesthesia away and force you to stare at the warped… grinding machinery inside his skull…the levers he jerks…the gears that grind against reason…the sparks that fly when reality collides with impulse.

This is not just a portrait of a man unfit for power; it’s a hazard assessment of a walking…talking catastrophe. And the more we keep these moments in focus…the harder it becomes for his madness to ever be normalized again.

I’ll be back soon!

Best,

-Jack