MindWar: The Psychological War on Democracy

MindWar: The Psychological War on Democracy

Little Excursion: Trump’s Very Bad Poker Game

Is Kharg Island the next grand adventure to entertain the mad king?

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Jim Stewartson
Mar 15, 2026
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I love poker. It is a purely mental sport requiring mental toughness, discipline, an understanding of the math behind every hand, and the ability to psychologically manipulate your opponent—without being manipulated yourself.

Wartime geopolitics has a strong overlap with poker’s skill set—a complex mind game where the chips are human lives.

Now, imagine playing poker with Donald Trump. He is the ideal opponent. As a player myself, he is the rare whale that sits down at the table with a great deal of bluster, quickly empties his wallet, and blames the dealer for it.

Gullibility is a trait everyone knows can get more pronounced with age. It’s just a known fact that as people age they can sometimes become easier to manipulate through simple psychological tricks. This is particularly true in patients with dementia. The science is clear.

Demented Nation: Five Years of American Free Fall

Demented Nation: Five Years of American Free Fall

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In a poker game, of course, gullibility is synonymous with losing your chips. In a war, gullibility is synonymous with getting slaughtered. Ask Neville Chamberlain.

Chamberlain, But Much Worse

Chamberlain, But Much Worse

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Another important skill in poker is the ability to control one’s emotions, to keep a straight face—a poker face—no matter how stressed you are. Being able to read an opponent, and not be read yourself is the entire difference between good players, and “fish”—who are there to feed the sharks.

In poker, as in war, you must be patient, and not get emotionally triggered by losing a hand, or being taunted by other players—or world leaders. Otherwise, you will play right into their hand and lose even more.

Finally, when you repeatedly take deceptive actions that have a predictable motivation, like bluffing too much, it ceases to be deception. At that point it becomes known as a tell.

Donald Trump is a human tell. He is a fish. In a pool of sharks.

Kharg

Early Saturday morning, Trump unleashed a Truth Social post in his usual absurd style with a very specific announcement and follow-on threat. Trump boasted about bombing Kharg Island—a tiny island (7.7 sq. mi) off the coast of Iran in the northern Persian Gulf which serves as a major oil hub, where 90% of Iran’s oil is distributed.

“United States Central Command… totally obliterated every MILITARY target in Iran’s crown jewel, Kharg Island… but, for reasons of decency, I have chosen NOT to wipe out the Oil infrastructure on the Island.”

Trump warned, however, that if Iran does not allow traffic through the Strait of Hormuz, that he will “immediately reconsider this decision.”

But when Trump tells you he’s doing something for “reasons of decency,” that is always a tell. He has never thought about decency in his life, unless he’s using it to conceal a different purpose. But what is he concealing?

Occupy

I believe that Trump is considering, if not already decided on, a ground invasion and occupation of Kharg Island—to seize the oil infrastructure in an attempt to monetize it. There is little difference in terms of flouting international law than his adventure in Venezuela where he invaded Caracas, kidnapped Maduro, and extorted the existing government into giving him billions of dollars in oil to sell to his friends.

But, unlike Venezuela which needs a decade and billions in investment to fully take advantage of its massive but difficult-to-refine oil reserves, Iran’s oil infrastructure is fully functional. 1-1.5 million barrels flow through Kharg Island every day, continuing even during the war.

Trump will never blow that up, because it would permanently raise oil prices and create an even bigger problem than he already has. What he wants is to control it, to create revenue from it. The idea of seizing millions of barrels/day of “liquid gold” from the Iranians may be too tempting for him to give up.

Pieces Are Moving

There are several other disconcerting data points that lead in the direction of some kind of raid—if not a full occupation—of Kharg Island.

First, immediately following the bombing of military targets on Kharg Island, and his ultimatum to reopen the Hormuz Strait, Trump sent the USS Tripoli along with 2,500 Marines from the 31st Marine Expeditionary Unit, which specializes in amphibious landings. This is a force highly capable, in theory, of taking Kharg Island.

USS Tripoli

Second, Trump was asked Friday on Fox and Friends whether he takes the advice of military advisors about the war. He said this:

“Even if I let them speak their minds, I convince them all to do it my way.”

Needless to say, if you always convince your own advisors to do it your way, you don’t have advisors, you have sycophants.

Third, seizing Iran’s oil at Kharg Island has long been a dream of Donald Trump, who was asked in a 1988 Guardian interview what his policy toward Iran would be as president. He said this:

“I’d be harsh on Iran. They’ve been beating us psychologically, making us look a bunch of fools. One bullet shot at one of our men or ships and I’d do a number on Kharg Island. I’d go in and take it. Iran can’t even beat Iraq, yet they push the United States around. It’d be good for the world to take them on.”

For at least 38 years, Trump has held this “psychological” grudge. And now it appears he is taking the opportunity to follow through.

But What Are the Downsides?

The dangers of such an operation would be extensive:

  • Kharg island is just 16 miles from the Iranian coast, making it exposed and vulnerable to attack. Should Marines take it over, they would be sitting ducks.

  • Any measures the Iranians may have taken to prevent an occupation like this are unknown. They may have booby-trapped the island, for example.

  • Taking Kharg Island would be expensive, dangerous, and result in casualties. A ground assault on the Island, regardless of the bombing campaign, would be met with opposition—on their turf.

  • It is unclear what would happen to the more than 8.000 residents of the island, and the thousands of workers who keep the oil flowing. Would they be effectively taken hostage?

  • Such a raid would be wildly illegal, but that hasn’t stopped Trump before. There is little legal difference between seizing Venezuela’s oil and Iran’s.

  • Seizing 90% of Iran’s oil revenue would cripple its economy, make Tehran’s leadership even more radical and desperate, and make more terrorism its only option. The war would widen, not stop.

Examples of such militaristic folly are plentiful. Small targets with strategic importance like the Suez Canal, Falkland Islands, Grenada, the Bay of Pigs, Iraq, Afghanistan, and Kuwait have historically been scenes of embarrassment, disappointment and death, not victorious conquest. And the failure of Operation Eagle Claw, the attempted rescue of hostages from Iran by Jimmy Carter in 1980, was a major factor in his losing the election later that year.

No Cards

A year ago, Donald Trump and JD Vance ambushed Ukraine’s President Zelenskyy in the White House and tried to browbeat him into surrendering to Putin. Trump said to Zelenskyy that he had “no cards” to play. Zelenskyy, incredibly, kept his poker face on.

Psychological Head-On Collision: The Existential Stakes of Zelenskyy’s Gambit

Psychological Head-On Collision: The Existential Stakes of Zelenskyy’s Gambit

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Since then, even though Trump has done everything possible to help Russia, to force Zelenskyy’s hand, Ukraine has not just held its ground but pushed Russian lines back on the battlefield. On the other hand, Russia, until the war in Iran at least, was on the road to economic collapse.

So far, there two beneficiaries of Trump’s “Little Excursion” in Iran: war criminal Bibi Netanyahu, and war criminal Vladimir Putin.

  • Netanyahu is getting to fulfill his lifelong dream of decapitating Iran, and getting high approval ratings in Israel, while he continues to use war to stay out of prison, largely on America’s dime.

  • Putin is getting a massive windfall, just as his economy was on the verge of collapse, because high oil prices make his exports profitable—and because Trump removed sanctions on Russian oil, despite Putin helping Iran target American troops.

Donald Trump may believe that Kharg Island is his “ace in the hole,” an easy target that will make the expense in American treasure and lives from his war of choice worth it. He may think he can just “go in and take it.” But in reality, he is a fish swimming in a pool of sharks.

Zoom today at Noon PT / 3PM ET for paid subscribers. We’ll discuss the last week’s events, and for those curious, I’m now free to talk more about my team’s legal victory over Mike Flynn. As always, it’s wide open for any questions and comments. Hope you can make it! Details below.

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