In the lead-up to the 2003 Iraq invasion, I was stationed at the Pentagon as a strategic officer, gaining unique insights into military strategies, intelligence evaluations, and high-level discussions. I frequently participated in meetings chaired by Secretary of Defense Donald Rumsfeld and Chairman of the Joint Chiefs of Staff Richard Myers.
From an outsider’s perspective, it seemed that Washington was exuding confidence. The Bush administration projected certainty, and much of the media seemed to align with this sentiment.
However, that’s not how I felt.
As I gathered more information, I found myself filled with questions. What would victory entail? How many soldiers would we require? What would follow the takeover of Baghdad? Were we ready for a prolonged occupation? Did we have a full grasp of the political, tribal, and religious dynamics we were about to unleash?
Such uncertainties were often overshadowed by a belief in the U.S. military’s superiority.
The regime fell rapidly, but war wasn’t as straightforward as that.
Since then, the U.S. has endured over 4,400 deaths, more than 32,000 injuries, and costs exceeding $2 trillion. This conflict also set the stage for ISIS’s emergence, a continuing threat in the region.
Now, 100 days into the war with Iran, I find myself revisiting many of those same questions.
The tenuous stalemate that began in early April appears to have collapsed. On June 9, an Iranian drone struck a U.S. Army AH-64 Apache helicopter near the Strait of Hormuz, marking the first Apache loss in this conflict. Thankfully, both crew members were rescued and reported safe. President Trump remarked on Truth Social that “the United States must inevitably respond” to this attack, leading to a retaliatory action by U.S. Central Command on the same day.
In response, Iran targeted U.S. military installations in Bahrain, Kuwait, and Jordan. This was the second day of Iranian strikes against U.S. forces in the area.
On June 10, the U.S. executed another round of attacks, this time hitting multiple sites in Iran. The Strait of Hormuz, which plays a crucial role in global oil transport—accounting for 20%—is still contested. On Wednesday, Brent crude prices climbed to $91.10 per barrel. The S&P has seen a decline of 4.5% since its peak on June 2.
Despite ongoing bombings, President Trump assured reporters that a deal was “a few days away” and that the strait would be reopened “immediately” if Iran signed. Iran’s parliamentary speaker claimed that Trump’s public remarks “contradict parts of the agreement,” indicating Tehran does not perceive an imminent deal.
I can see the rationale behind the government’s stance. The escalating costs might eventually lead Iran to recognize that compromising is preferable to ongoing sanctions. Yet, history shows that things are rarely that straightforward.
Iran has been responding in this way for almost 50 years. They negotiate, delay, and demand concessions, seeking influence without making irrevocable commitments.
I previously pointed out that a major misjudgment in Washington is the belief that Iran thinks like we do. While America seeks a resolution, Tehran’s priority is survival. Whereas America desires closure, Iran needs time.
A framework set in late May, as a 60-day memorandum, allowed Iran to resume oil sales and placed a temporary halt on enrichment in exchange for sanctions relief, with a pathway to nuclear talks. Iran’s foreign minister hinted that a deal was “very close,” while also accusing U.S. negotiators of making “extremist demands.”
This cycle of advances and setbacks has characterized Iranian diplomacy since 1979. It’s baffling that we continue to expect different outcomes.
Now, President Trump faces three critical choices, each carrying unacknowledged costs for the U.S. government.
The first option is escalation. If the intent is to dismantle Iran’s nuclear ambitions permanently, and if Tehran resists, the logic may lead to something larger than airstrikes. Iran is not Iraq; it’s larger and more densely populated, with significant geographical challenges. The required forces would far exceed those deployed during the Iraq invasion in 2003, which involved a coalition of several nations. Currently, no such alliance exists for action against Iran. Mobilizing not just active-duty soldiers but also National Guard and Reserve units, without the support that was present in Iraq, has yet to be honestly presented to the American public.
Gaining control of Tehran will be challenging, and maintaining it could demand a long-term commitment. Predicting subsequent developments will be even harder.
The second option involves long-term containment. This requires acceptance of an uncomfortable truth: Iran will likely never willingly negotiate away what its leaders see as a strategic need. Containment would consist of military deterrence, sanctions, maritime security, intelligence operations, and strengthening regional alliances. It necessitates patience, not grand declarations. Although it lacks the appeal of a decisive victory, it better aligns with confronting a regime focused on longevity rather than election cycles. The strategy of containment effectively kept the Soviet Union at bay for half a century, backed by mutually assured destruction. The same principle applies in this situation.
The third option is an armed ceasefire. This is where Trump currently stands. Even with recent strikes, negotiations persist. Yet any agreement must be evaluated based on its practical outcomes rather than just promises. Pacts that freeze hostilities while leaving fundamental issues unresolved will only delay the next conflict, often at a greater cost.
I have previously discussed that adversaries like Iran evaluate situations in terms of generations. They absorb today’s setbacks to enhance their position for tomorrow. Every week without a definitive ceasefire regarding denuclearization allows the Iranian government to regroup and strategize, waiting for Washington’s political climate to shift.
The real challenge for the president isn’t a lack of military strength; the U.S. remains preeminent in that regard. The pressing challenge is to articulate realistic political objectives and be transparent with the American populace about the associated costs.
If the aim is to overcome the regime, Americans deserve straightforward information about the scale, duration, and human toll involved.
If containment is the goal, then the government ought to refrain from suggesting that more bombings will compel Tehran to concede.
If seeking a negotiated settlement, the focus must shift to validation rather than optimistic timelines. The prospect that Iran could agree today and adapt tomorrow is still uncertain.
The most challenging inquiry facing President Trump now echoes the questions I posed during my time at the Pentagon before Iraq.
It’s not about whether America can win a military engagement. We can.
It’s not even about the capability to destroy specific targets. We are capable.
The crux of the matter revolves around what political ramifications will legitimize the ensuing events, and whether we’re prepared to confront that truth before another Apache goes down.
The battle of choice starts with a sense of assurance but concludes when leaders find themselves confronted with unavoidable decisions.
