Why Counterinsurgency Doesn’t Work + What’s Next with Iran?

It’s easy to see why presidents have avoided ripping the bandage off for 47 years.

If we’ve learned anything from the online derangement chambers, such as X, it’s that holding the most powerful office in the world is easy business as long as it is held from the comfort of a couch, with smartphone in hand. From that vantage point, naval vessels and ground forces are plastic models and figurines that can be moved from one piece of key terrain to the next, and commodity prices are adjustable with the click of a button.

That same strategic viewpoint allows for key pieces of legislation to pass through flimsy majorities, and America to be made great again through sheer willpower, decades of civic inaction be damned. Back in the real world, President Trump has reminded our people exactly why the Iranian quagmire is what it is:

Reagan buzzed the tower in 1981 and told that regime there was a new sheriff in town, but decades have passed and Iran has morphed into a key enabler of Chinese military ambition set to cause major heartache for American geopolitical strength by mid-century. You can read my March piece about why actions in and against Iran are more linked to China than they are to Israel, or the latest brain rot available on X, here:

With that said, my support or understanding for the military efforts in Iran has limits. I believe the current fears of the MAGA coalition over Iran stem from any combination of three factors:

• Fear that U.S. forces will become entrenched in a prolonged conflict (regular or irregular conflict)

• Prolonged disruption of commodity prices (fuel cost)

• Being misled by other nations as to the true threat of Iran and capitulating to “globalist” causes

Trump, on the other hand, has promised to bomb Iran for decades if necessary, and has campaigned for a decade on having a military bigger and stronger than anything America has ever had, which is saying something. That doesn’t exactly seem like he’s viewed the Iranian regime as a bunch of peace-loving hippies trying to spread love and good vibes when they say “Death to America.” The ugly truth is always somewhere in between the extremes, and if your negative perception of the efforts in Iran is tied to how you view Israel, I would encourage you to adopt my viewpoint:

Don’t trust any foreign government no matter their relationship to the United States. Don’t even trust your own government. Be an equal opportunity hater.

Here is what I had to say on March 2 about successful military outcomes:

• No conventional forces deployed on the ground

• Khamenei and line of succession eliminated

• Pro-West head of state in power

• Economic benefit to the United States

Seven weeks later, there are still no conventional forces deployed on the ground (there are most certainly special operators and teams), Khamenei is long dead and there has been enough attrition that the foundation of the regime is cracking and bending to pressure, and the current situation in the Middle East appears to be the leverage point as to how the economics of this dust-up will shake out. The only glaring missed objective here is the third - a pro-West head of state in power.

In order to get that, it will require the Iranian people doing the dirty (and bloody) work of eradicating all traces of the regime and preventing the IRGC from holding power, or it will require a lot of American lives lost in conventional ground conflict and the ensuing counterinsurgency operation. The President knows that, and I am confident the second option is no option at all. He also knows that uprooting a regime through air strikes and naval maneuvering isn’t going to happen. Online bettors don’t see the regime completely falling anytime soon, either:

In my book, The American War on Election Corruption, I wrote extensively about my time in Afghanistan, especially about the moment in which I realized we would never win there. That moment ushered in the beginning of the end of my military career, which would drag on for another 3 years before I made it final that I had no further interest in investing my prime years in an unwinnable effort to pacify a warlord-run nation. These things were clear to me after reading a book you must own, Counterinsurgency in Modern Warfare:

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Why Counterinsurgency Fails and What it Means for Iran

History is full of counterinsurgency efforts, and almost all of them have been miserable failures.