What Does History Tell Us About Trump vs. Iran?

Ruinous quagmire or breakthrough success?

Many are watching the military escalation in the Middle East with bated breath, worrying that President Trump will wreck his legacy trying to force a regime change against a decades-long enemy, Iran. Before you advance in this article, a good use of five minutes would be to watch CENTCOM Commander Admiral Brad Cooper’s update from yesterday:

What I am writing today can be read by anyone on any side of “Iran opinions” spectrum. It is about facts and objectives more than about convincing you which course of action is best.

The conventional phase of the conflict is shaping up like the first days of Desert Storm, with the U.S. and its allies crushing the Iranians like a tin can. Bombing runs are now underway within Iranian airspace with little surface-to-air threat present thanks to initial operations to defang their defenses. We already know Trump is creating jobs in Iran daily with each vacancy report within the Iranian regime. You don’t need me to read you the news; you can do that yourself. My objective here is to help you make sense of it all and what is truly means for the future of the Trump administration and by extension, the United States.

People are losing their minds online, especially over on X (sadly, I may be back on soon because it would be stupid to release a book and not use all my social media to advertise it). Marjorie Taylor Greene has already broken from what she desired to be a level-headed voice of accountability and is now posting deranged commentary that goes beyond the tolerable limits of “libertarianism.” Others have overlooked Trump’s promises from a decade ago to stave off Iranian aggression, and are acting like official White House releases as far back as 2018 never happened.

Trump decried regime change for many years, and yes, it does look like we are on azimuth to push for exactly that. Critics pointing this out aren’t wrong. Here is how I put it in Monday’s column:

Trump has railed against regime change, a valid criticism, but no situation remains static forever and a run-only football team may find itself in a need to pass the football if they get down too much and don’t have enough time to run the football. So it is with being limited to a four-year term thanks to the theft of the 2020 election.

The President is looking to remake the world with his vision for future American prosperity and success in mind and doesn’t have long to do it. He is acutely aware the rest of the world, and even our own political “leaders,” are trying to wait him out get back to business as usual. So even if pushing a regime change in Iran is against what was advertised, no one ever said there would be no use of the United States military or that it would even be possible for us to sit on our hands while the adversaries of the future make strategic moves to leave us in the dark in a rapidly changing world.

You don’t have to like it. But it all points to a bigger picture, and I will take you back to my own experiences in Afghanistan to make the point.

First Lieutenant Keshel went to RC-West and spent a year tucked in the shadows of Iran’s eastern border; I arrived in-country a believer that our efforts there were worthwhile, and left believing long-term success there was impossible (and I was correct). What was shaping up to be a career in uniform was less than three years from closing time because I lost faith in the mission. The year I was there, 2010-11, was known for green-on-blue attacks. A quick breakdown:

• Blue Forces: good guys (U.S. and coalition partners)

• Red Forces: bad guys

• Green Forces: (local Afghan forces, like the Afghan National Army and Afghan National Police)

The tactical goal, if anything could be defined as such, was not much different than any other counterinsurgency in the history of military operations: train the host nation to take ownership of security and eventually turn it all over to them.

The only problem, then, was that the green forces were heavily invested in shooting Americans in the back of the head at chow more than they were in risking life and limb at the hands of their Afghan brethren. In our area of operations alone, the Afghan National Police and Army were well known to trade military equipment (given to them by coalition forces) to the Taliban in exchange for not being attacked, and the Police in particular would claim ammunition expenditures (for replenishment) that never happened because they were handing over extra ammo in exchange for cash to people who wanted to pump it into Americans.

Afghans, like their Iraqi counterparts, were terrible partners in a pair of conflicts unwinnable from the start. If you’re not squeamish about foul language, watch this Army officer berating a bunch of Iraqi forces for exactly what I’m talking about. The Secretary of War, Pete Hegseth, and the President most certainly know that involving conventional American forces (beyond special operators who are already in country) on the ground would result in a major reversal on campaign promises and a serious loss of political capital.

So now what? We are pushing for “regime change” and still intending not to enter the country?

The problem here is that military history tells us it isn’t possible to hold down a piece of territory, or oust existing leaders, without boots on the ground. If the administration is to keep its promise, yet still oversee the removal (or extreme pacification) of the Iranian regime, then it means we are about to observe something never before seen in the history of conflict.

The Intelligence Edge and How Iran Falls