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Al-Makahleh: When War Outruns Strategy: Notes from a Closed-Door Conversation in Washington

Dr. Shehab Al-Makahleh

On Friday afternoon, I attended a closed-door meeting with a senior investment adviser in Washington whose career spans multiple U.S. administrations and institutions. Over the past four decades, he served in roles connected to the administrations of Ronald Reagan, George H. W. Bush, Bill Clinton, and George W. Bush, before moving into positions within the U.S. Department of Justice and the U.S. Securities and Exchange Commission. In recent years, he has become a strategic adviser to several hedge funds and multinational corporations that rely on such figures for their deep networks inside Washington—particularly within the Pentagon, intelligence circles, and the national security establishment.

The meeting brought together a small group of investors and analysts seeking a comprehensive briefing on the rapidly evolving confrontation involving Iran, Israel, and the United States. What emerged from that discussion was a picture not only of a war unfolding in real time, but of a strategic environment in which events have moved faster than the planning structures designed to manage them.

According to the adviser’s assessment, the most striking element surrounding the launch of military operations against Iran was the absence of a traditional war-planning framework. The campaign, he indicated, began without the establishment of a formal war council and without the full range of scenario simulations that normally precede a conflict of this magnitude. In other words, the escalation was driven more by political momentum than by a carefully staged strategic process.

The political dynamics behind the decision were equally revealing. Within Washington, the push toward confrontation was shaped by pressure from Benjamin Netanyahu and a receptive audience in the White House under Donald Trump. While some senior figures initially expressed reservations—including Secretary of State Marco Rubio and Vice President JD Vance—the internal debate ultimately tilted toward escalation. According to the briefing, Rubio eventually aligned with the pro-war camp, while Vance maintained a more cautious stance.

What appears to have surprised Washington most, however, was Tehran’s response. The original expectation in some policy circles was that the conflict would begin with limited exchanges between Israel and Iran, followed by targeted strikes against senior Iranian leadership. The assumption was that such actions might force Tehran toward negotiations, enabling the White House to declare a form of strategic victory.

Instead, the opposite occurred.

Iran chose rapid and comprehensive escalation, including the closure of the Strait of Hormuz and strikes against American interests across several Gulf states. That response has significantly disrupted the initial calculations in Washington. According to the adviser’s description of internal thinking, the U.S. administration now faces the reality that Tehran—at least for the moment—holds the initiative in determining the pace and scale of escalation. Attempts by Washington to establish back-channel communications in recent days have reportedly been rejected by the Iranian side.

Another emerging concern involves maritime security. Officials increasingly doubt that the United States can fully guarantee freedom of navigation through the Strait of Hormuz under current conditions. As a result, the immediate strategy appears to focus less on reopening the corridor and more on mitigating the global economic impact of its disruption—particularly on energy markets.

Meanwhile, another strategic complication may arise from Israel’s military priorities. American analysts believe that if Israel launches a large-scale ground operation against Hezbollah in southern Lebanon, a substantial portion of its air assets could be redirected from operations against Iran. Such a shift would reduce the overall level of Western air dominance over the Gulf and Iranian airspace.

At the same time, the logistical dimension of the war is beginning to strain U.S. capabilities. The Pentagon is already grappling with the challenge of replenishing missile inventories and other critical systems being consumed in the conflict. Some naval planners are reportedly resisting calls to redeploy additional carrier strike groups from the Pacific to the Gulf, warning that such a move could signal weakness to China and reinforce the perception that the United States cannot sustain simultaneous conflicts across multiple theaters.

Perhaps most telling, however, is the reaction of the Gulf states themselves. According to the adviser’s account, governments across the region are reluctant to become direct participants in military operations against Iran. Their hesitation does not necessarily stem from sympathy toward Tehran. Rather, it reflects a lack of confidence in Washington’s ability to manage the escalation and protect regional partners from retaliation. Gulf leaders are acutely aware that their infrastructure, ports, and financial systems could become immediate targets if the war widens.

Taken together, these insights point to a broader reality: the strategic architecture surrounding this conflict remains unsettled. The war’s opening phase has already disrupted assumptions about deterrence, escalation, and control. What was initially envisioned by some policymakers as a contained confrontation has instead evolved into a volatile contest in which the pace of events may be exceeding the ability of any single actor to manage them.

The Friday discussion in Washington made one point unmistakably clear. Wars do not simply test military strength—they test planning, alliances, and the credibility of political leadership. In the current crisis, all three are now under scrutiny.