In the months leading up to the launch of Operation Iraqi Freedom and the invasion of Iraq in 2003, I was asked to present a professional development session for our brigade leadership on the coming war. After spending more than a year as a division planner, I had been read in on the planning from the outset. As a Gulf War veteran, I had on ground experience and knowledge of the region.
The presentation itself was relatively straightforward. But I included one slide that conveyed the worst-case scenario we had discussed many times in the bowels of the SCIF: and irregular, urban-based fight.
There were many who expected a replay of the 100-hour ground phase of Operation Desert Storm. But there were some – myself included – who assumed that the Iraqi Army had learned from that experience and weren’t about to repeat it. So, if you’re a third-rate military force equipped with outdate Soviet equipment that barely survived your last major conflict, how do you avoid another beat down?
Don’t get caught out in the open.
In other words, pull the fight into the cities. Drag our conventional forces into an irregular fight and wage a different kind of war. A long war that tests political resolve and national will.
That was the worst-case scenario, our own version of the classic Kobayashi Maru. And, ultimately, exactly what they did (and we even helped them along the way with some remarkably bad decisions).
What Is The Kobayashi Maru
Fans of the Star Trek universe have always been fascinated with the Kobayashi Maru, the fictional training simulation prominently featured in the 1982 blockbuster, Star Trek II: The Wrath of Khan. Designed by Starfleet Academy, the simulation presents command-track cadets with a deliberately worst-case scenario intended to test character, leadership, and decision-making under impossible circumstances.
In the simulation, a cadet commanding a starship receives a distress call from the Kobayashi Maru, a civilian vessel stranded in the Klingon Neutral Zone. The cadet faces two equally grim options: enter the Neutral Zone to attempt a rescue — triggering an overwhelming and decisive Klingon response that is sure to destroy both ships — or abandon the Kobayashi Maru and its crew to their fate. No tactical solution exists that saves everyone. The test is not meant to be passed; it is meant to be failed.
The scenario’s value lies precisely in that impossibility. Starfleet uses it to observe how future leaders respond to worst-case, no-win situations — whether they panic, freeze, compromise their principles, or accept loss with grace and clarity. It probes the ethical and moral core of leadership: how does a leader cope with death, the weight of responsibility, and the limits of their own power?
Worst-Case Scenario Planning Process
In his 2009 novel, Gone Tomorrow, author Lee Child sums up the essence of worst-case scenario planning with an on-brand quote from the lead character, Jack Reacher: “Hope for the best, plan for the worst.” Worst-case planning isn’t pessimism. It’s the harsh realism and discipline that allows planning to transcend “the enemy gets a vote” factor. If you account for the absolute worst outcome possible, you will inevitably find the flexibility and adaptability that subordinate leaders require to pursue an objective with autonomy and purpose.
As a war planner, strategist, and even in daily life, I have always leaned into the worst-case perspective. Not because I have a pessimistic, Eeyore-style worldview; the opposite, in fact. I can afford to be optimistic because I’ve thought through and addressed the worst-case scenario. For me, it’s simple five-step process.
1. Define the worst case explicitly.
Vague fears can paralyze decision-making; named risks are manageable. This is a key element of Nassim Nicholas Taleb in his 2007 book, The Black Swan. Worst-cast thinking transforms decision anxiety into actionable planning.
2. Wargame before execution.
In a 2007 Harvard Business Review article, “Performing a Project Premortem,” Gary Klein – probably my favorite writer on strategic thinking – underscored the absolute necessity of wargaming. Imagining a project or operation has already failed — then working backward from that point — surfaces blind spots that uniformed optimism conceals.
3. Separate likelihood from impact.
This is a classic intelligence wargaming technique highlighted by Daniel Kahenman in his groundbreaking 2011 book, Thinking, Fast and Slow. Low-probability, high-consequence events demand disproportionate attention.
4. Build response protocols in advance.
Decision-making degrades under stress. Pre-determined and developed options – what we often define as branches and sequels in military planning – preserve clarity of thought when pressure peaks.
5. Normalize failure as data.
In her 2018 book, The Fearless Organization, Amy Edmondson cut to the chase on postmortems. Organizations that treat failure as shameful suppress the information needed to improve. That’s why after-action reviews or hotwashes are absolutely necessary in the wake of a failed project or operation.
The Iran Conflict’s Worst-Case Scenario Planning
Where does all this lead? Iran.
There was no scenario in which the United States would not prevail in a conventional fight against Iran’s military forces. And if the goal was regime change, the combined effect of the early strikes, as described by the secretary of defense, “cut the head off the snake.”
Except Iran isn’t a snake. It’s a Hydra.
The current situation in the Strait of Hormuz is only the beginning. The strait is a tipping point for the global economy. As CNBC noted recently, “Oil is far from the only critical input for the global economy” that transits the strait. The Middle East accounts for nearly a quarter of the world’s aluminum exports, a third of the global fertilizer trade, and a fifth of planet’s natural gas supply. In a highly integrated and globalized supply chain, the full downstream effects have yet to be seen and will be economically significant for months, if not years, to come.
Iran also possesses one of the most globally far-reaching cyber warfare capabilities. Working closely with countries like Russia, Iran built a network of both government-aligned and hacktivist cells that can be activated from anywhere in the world will no warning whatsoever. Despite our own claims of obliterating their nuclear capability, Iran still possesses enough enriched uranium (more than 400 kg) to produce 10-12 weapons with additional refinement. And they hold enough material in various stages of enrichment (over 6000 kg) to wreak havoc in other ways. Finally, Iran’s proxy networks and global terror infrastructure are extensive, with an established presence across the western hemisphere. Recent attacks in the United States served as reminders of our own vulnerability. These networks won’t target hardened capabilities – they’ll focus on soft targets that maximize public terror.
If we haven’t done our worst-case scenario planning, now might be a good time to start. We may have cut the head off the snake, but now we’re dealing with the aftermath, and it can – and might – get a lot worse before it gets better.
