“Judge your enemy based up capabilities, not intent, you have to look at the enemy and really almost make a worst case call every time.” General Norman Schwarzkopf
Failure to prepare for the worst case scenario based upon their capabilities is one of the worst errors a commander can make when faced with adversaries. That failure often goes arm in arm with underestimating your enemies capabilities or ignoring their capabilities because you believe your own are so far superior and your people are superior in courage, resolve and martial ability.
A prime example is Peal Harbor. The U.S. knew that Japan had the world’s most numerous and most advanced carriers. For years there had been warnings about the possibility of an attack by Japan there. Instead of preparing for Japan’s capabilities the U.S. listened to Japan’s stated intent which was to continue negotiating. Also, the U.S. military vastly underestimated the effectiveness of Japan’s navy and army and also disparaged the Japanese, often on racial grounds as being inferior to Americans in nearly every respect. This refusal to acknowledge Japan’s capabilities led to the worst naval defeat in U.S. history.
Another example of failure to account for your enemy’s capabilities is that of Israel in the Yom Kippur War of 1973. Egypt had massively increased the size of their armed forces and their number and quality of their tank forces with the assistance of Russia. The quality of Egyptian soldiers’ training had also undergone an exponential improvement. Israeli intelligence reported all this, but military leaders and those in power in Israel discounted these new capabilities partly due to the fact that Egypt had submitted peace proposals for the return of Sinai to Egypt. Also, Egypt had been engaging in routine maneuvers for months prior to the war and Israel believed that the assembly for the war was part of an announced maneuver. Israel relied upon their adversary’s stated intentions. Further, Israel did not take a worst case look at Egyptian capabilities. Israel had also failed to consider the capabilities of the Syrians who attacked with 600 tanks, causing the collapse of the defending Israeli armored brigade. They looked to their previous overwhelming successes against Egypt and Syria and discounted all the reports about new Russian tanks and training.
Therefore, when Egypt crossed the fortified Suez canal with 100,000 troops, 1,350 tanks an 2,000 artillery and heavy mortars, Israel had only 450 soldier spread out along the 16 forts along the canal and there were only 290 tanks, divided in three brigades. Only one brigade was anywhere near the Egyptian assault. The attack actually was such a surprise that it was an existential threat to Israel. This strategic error has been studied as a prime example of failure to consider an enemy’s capabilities on a worse case basis. Further, you underestimate your enemy at your peril.
Trump is guilty of both of these basic strategic errors. We now know as of March 14, 2026 that the Chairman of the Joint Chiefs of Staff warned Trump directly about the closure of the Straits of Hormuz and that they would likely use mines, missiles, and drones, to close the Straits. Trump chose to ignore that advice and rely on his cronies in the cabinet. The military told Trump about Iran’s capabilities. It is the duty of any military commander to prepare for that worse case scenario. The failure to do so is probably dereliction of duty and could be a courts martial offense.
Secondly Trump massively underestimated his opponent based on his gut feelings and his prior experience having on two previous occasions made strikes against Iran or an Iranian General. His cronies in the cabinet told him, without any basis in fact, that Iran would likely fold, and that in the past strikes on Iran had been without impact on the oil market. Trump relied on his judgement as to what Iran’s intentions were. This is an exercise in mind-reading. Faith, hope and gut feelings are not effective strategies in warfare. The only reliable method to conduct a war is to assume the worst about your enemy’s capabilities and prepare for that. And even then you get surprised. If you don’t prepare for the worst case, you end up all to often losing that war.
