5 Things America's Leaders Misunderstand About War with Iran
Donald Trump Needs More Art of War, Less Art of the Deal
Hi, I’m Christopher, I’ve passed the Foreign Service Officer Test (FSOT) and studied topics of international affairs both formally (B.A. in Global Development Studies, M.Sc. in International Business), in my career (e.g. consulting for an international auto brand on EV supply chain risk), and for fun (my YouTube “Watch Later” list is basically just hours of geopolitics haha).
One of the most frustrating parts of being informed about diplomacy is watching people who shouldn’t be leading war and negotiations horribly flub both. Here’s what I wish our present leaders actually understood.
1) Desperate ground.
Over 2000 years ago, Chinese strategist Sun Tzu wrote, “When you surround an army, leave an outlet free. Do not press a desperate foe too hard.” He elaborated elsewhere on the strategic utility (and danger to attackers) of desperate ground for a defending force. I wrote thoroughly on this strategic principle of war here last week.
You never want your opponent to be in a situation where their only options are fighting you in desperation or giving themselves up to death (or fates they view as worse than death). They will fight you, and while you may win, they will make it cost you as much as they can.
This is not what you want in war.
2) You have to leave something to lose.
For peace negotiations to work, your opponent needs something to preserve — or something to gain. Iran’s economy is in ruins. Their domestic standing was already shaky. We killed much of their leadership immediately, including Supreme Leader Khamenei, and even the wife of the new Supreme Leader, Mojtaba Khamenei.
The problem is (although I think this is actually a good thing), we lack the appetite to commit the ground presence necessary to “finish the job” and install a new regime, meaning we need to negotiate some sort of peace with what remains of the regime.
But then you have to ask yourself: what exactly are they supposed to be negotiating for? The regime has much less to lose by continuing fighting now than they have to gain from continued pressure, both tangibly and “emotionally.”
While there are some strategic objectives the Iranians would desire, such as guarantees of no future strikes, right now, fighting back is the only move that lets them save face, even if continued war were to logically be a negative for them.
Which brings me to the next point.
3) You have to understand who you’re fighting.
Retired U.S. Army lieutenant general H.R. McMaster calls this “Strategic Empathy.” Understanding the dynamics and motivations of your opponent is critical. Iran operates in an honor/shame culture. When we and/or Israel struck them in the past, they responded with dramatic, flashy retaliation with minimal real damage — loud enough to look strong at home, careful enough to avoid real escalation.
It was calculated performance. It met their domestic objectives of preserving their pride while avoiding further escalation that would put them at serious risk.
But what if there was no meaningfully “further escalation” to fear or desire to avoid? And what if the “dishonor” they felt they’d received was far more acute than a handful of bombed military facilities?
By coming in at 100 and destroying everything/everyone they’d want to preserve in any future peace negotiations, we removed motivations for restraint. We killed their leadership on day one. We’ve destroyed thousands of military targets. The incentive to stay measured? Gone. What do they gain (or not lose) now from suing for peace? In their mind, not much.
No, now they feel a need to save face. Not good.
4) Ideologies cannot be defeated with guns and bombs alone.
The Islamic regime within Iran is motivated by extremist Shi’a theology. To die is to be martyred. Death can be a victory itself.
If you don’t understand the Karbala paradigm, you’re going to risk ironically strengthening the regime’s hand with the damage you succeed in. Not only that, but every civilian death is an opportunity for the IRGC to say, “I told you so,” to their domestic population.
And brings up the last thing I wish our leaders demonstrated more cognizance about.
5) Populations rally against outside attackers.
To date, over 1,400 Iranian civilians are believed to have died in this war. As resources dwindle and further bombs fall, the population may begin to no longer see the regime as the primary cause of their frustrations, but the US and Israel.
The IRGC narrative regarding the popular revolts of several weeks ago has been that the Israelis and Americans manipulated the people; that we were the ones behind the uprising, and were merely using the people as pawns to achieve our strategic objectives. “The Americans are your oppressors, not your liberators,” they argue.
When we bombed the girls school in Minab, and/or if we at any point resort to bombing civilian infrastructure such as power facilities, we lose some of the very goodwill we were hoping would result in a domestic revolution. This war of supposed liberation could very quickly turn into a war that cements a foe who was previously fracturing, especially if we put boots on the ground.
In Summary
The reality is, none of Donald Trump’s predecessors initiated such a war because they recognized the massive costs and risks such a war would incur, not only militarily in the region, but also across both the regional and international economy. I remain doubtful that we can secure what we claim our objectives for this war are, absent boots on the ground (which I very much do not want to see).
At the same time, working towards peace will require far more tact and care than this administration seems to be interested in exercising. Donald Trump knows one language: the exertion of power. Not only power, but a very Western framing of power, in which everything is decided by calculus and self-preservation.
His understanding of motivations and self-preservation worked with Venezuela. Delcy Rodriguez (formerly Maduro’s VP), along with the rest of the Venezuelan regime, is primarily interested in her own self-preservation. Allowing her to cut deals to preserve her standing while selling out her boss worked in our favor.
Iran however, is not Venezuela.
Ideas of the priority of self-preservation and Western reasoning simply will not work here, and we desperately need diplomats in the picture who understand our enemies and how we can avoid any further development of worst-case scenarios and, hopefully, move towards some sort of peace before the cost of this war becomes scarring for us all.




Good article. You make solid, common sense points. Unfortunately, we are ruled by psychopaths.
I admittedly do not have enough background on these topics to form an educated and eloquent opinion yet, but I wanted to thank you for such a thought-provoking piece. Definitely given me more to reflect on.
Frankly, it's a breath of fresh air to hear well-articulated opinions with explanations of facts and context. This is a lot more persuasive and informative than 99% of the content and news I see online about topics like this!