Deeper and Deeper How Trump Got the U.S. into a Hole in Iran and Just Keeps Digging

By Rob C

TL;DR: There’s an old saying about holes: when you’re in one, stop digging. Nobody explained this to the Trump administration. Donny Draft-Dodger blustered his way into an unnecessary, unprovoked conflict with Iran, promising a “quick victory” and “total obliteration”. In June 2025, we were told Iran’s nuclear program was “completely and totally obliterated.” Then we were told it again and again. Meanwhile, the actual war never stopped — we’re now on the 12th consecutive night of strikes as of this week, the Houthis have opened up a second front by attacking Saudi oil tankers in the Red Sea, oil has surged past $100 a barrel, and the Secretary of Defense just went to Congress to explain why, after “winning” this war approximately four separate times, he needs another $70 billion to keep fighting it. This isn’t a war strategy. It’s a shovel, and they keep asking us to pay for a bigger one.

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Good morning. Let’s talk about a war that keeps getting “won” and somehow never actually ends.

The Cheeto-Flavored Misadventure

When you elect a man whose understanding of global geopolitics comes entirely from cable news chyrons and flattery from foreign autocrats, you shouldn’t be surprised when his foreign policy devolves into a disaster.

From the moment “Donny Draft-Dodger” began his latest Middle Eastern misadventure, he treated a conflict with Iran—a nation of 90 million people with a 1,000-year-old civilization—like a reality TV feud. He bloviated about bombing cultural sites, wiping out infrastructure, and committing blatant war crimes on social media.

Trump was easily flattered and manipulated into attacking Iran under the delusion that a few flashy missile strikes would produce instant capitulation. Instead, he stumbled into a strategic trap. The promised “easy wins” never materialized, and now his administration is trapped in a war of attrition with no defined end state, no exit plan, and no clue what to do next, and working Americans are left footing the bill for higher gas, expensive food, and endless conflict.

The Hall of Empty Declarations

Nothing illustrates the sheer incompetence of this administration quite like the gulf between their public statements and actual reality.

Trump and his Secretary of Disaster, “Testosterone Pete Hegseth”, have spent months spouting triumphant soundbites while the conflict worsens:

“Totally Destroyed” & “Obliterated”: Repeated claims that Iran’s nuclear capabilities and military infrastructure were completely wiped out—statements that immediately crumbled when administration officials had to admit Iran retained significant striking power.

“We Won” & Imminent Surrender: Early TV appearances assuring the public that Iran was on the verge of total surrender, only to follow up weeks later by launching new rounds of strikes.

Moving the Goalposts: Shifting from claims of “peace through strength” to threatening to hit deeply buried sites “very heavily,” moving the goalposts every time their previous strikes failed to secure a result.

When questioned by senators on Capitol Hill, Hegseth couldn’t explain how or when the war ends—he just accused critics of “Trump Derangement Syndrome” and demanded more money.

The Hole Gets Deeper

While Trump brags about imaginary victories, the real-world consequences are cascading across global markets.

If you were hoping this story might quietly wind down, I regret to inform you that the war has instead expanded to include a second chokepoint. This week, Iran-backed Houthi rebels in Yemen announced a naval blockade against Saudi Arabia and began attacking Saudi oil tankers in the Red Sea, hitting vessels near the Bab el-Mandeb Strait — the exact kind of second front that happens when you leave a regional conflict to simmer for months without an actual resolution.

Remember the ceasefire “memorandum of understanding” Trump struck with Iran back in June? Neither side is honoring it. It has, in the technical diplomatic sense, collapsed. And in the wreckage of that collapse, Brent crude oil has now crossed $100 a barrel for the first time in two months — up roughly 40% for the month of July alone — with energy analysts warning that further escalation could push prices toward $120. For context, that’s the kind of number that shows up directly on your receipt at the pump and, thanks to fertilizer and transport costs, on your grocery bill too. This war was never going to stay confined to news footage of missiles. It was always going to end up in your shopping cart, and here we are.

The Real Cost to Working Americans

While Donald Trump continues to brag about his Tic Tac numbers and profit off his private ventures, working Americans are paying for his war at every turn.

The $70 Billion Blank Check: Secretary Pete Hegseth recently marched before Congress to demand an additional $70+ billion in emergency war funding. That’s tens of billions of taxpayer dollars on top of what’s already been spent, with some reporting putting the actual cost as high as $200 billion, once you account for restocking munitions, poured into an unauthorized war that the American public never voted for and 70% actively opposes.

Pain at the Pump: Gas prices are surging past $4.00 to $4.50 a gallon nationwide, directly eating into family budgets. This doesn’t affect the billionaire class making a killing off the killing, but working families are getting bombed every time they fill up.

Pain at the Checkout: Surging fuel costs drive up transportation costs and fertilizer prices, which directly inflates the price of groceries on store shelves.

Trump is digging a financial and geopolitical hole that is swallowing billions of dollars—and the American people will be forced to pay off the debt long after he leaves office.