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Frederic B. Hill, a former foreign correspondent for The Baltimore Sun, covered part of the Iranian revolution in 1979 and later conducted wargaming exercises for the Department of State, including one in 1987 that was influential in the Reagan administration’s decision to reflag Kuwaiti tankers. He is author of the forthcoming book, “Over the Horizon: Foreign Policy Gaming in the Department of State.” He lives in midcoast Maine.
Mines laid in the Strait of Hormuz, the narrow passage in the Persian Gulf through which one-fifth of the world’s oil and gas flows. Small high-speed civilian boats. Missiles fired from the Iranian side of the Gulf to attack ships and planes and shut it down.
Sound familiar? It is similar to what Iran has done in the last month to counter-attack President Donald Trump and Israeli Prime Minister Benjamin Netanyahu’s war against Iran — and to effectively stymie their overwhelming military advantage and devastating assassinations of top leaders.
Yet many of the very same tactics were employed by a badly weakened Iran four decades ago at the end of the 1980-1988 Iran-Iraq war, one of the bloodiest conflicts in modern history.
Having suffered more than 500,000 deaths towards the end of that war, Iran began firing missiles and placing mines to attack oil tankers trying to move south from Kuwaiti and Iraqi terminals. It worked for a while — until the Reagan administration, under pressure from Gulf states and European leaders, decided to reflag the Kuwaiti tankers.
Deploying a powerful convoy of ships, the largest use of the U.S. Navy since World War II, the reflagging worked almost immediately. On July 22, 1987, two tankers flying the American flag, and three U.S. destroyers, headed through the Strait of Hormuz. Two days later, the 414,000-ton supertanker Bridgeton (originally the Al-Rekkah) was struck by a submerged mine near Farsi Island. Shortly after that, the U.S. forces seized an Iranian ship laying mines. The reflagging was a major factor in Iran’s agreement to end the war a year later.
Now Trump and his Defense Secretary Pete Hegseth have been set back in their unhinged — and to date far from successful — war against a new Iranian regime, a war of choice with a baker’s dozen goals. And, according to numerous news accounts, they have disastrously ignored the history of the region, as well as the stunning results of previous and contemporary wargaming by the Pentagon and a former State Department gaming office.
Current Pentagon generals and admirals no doubt conducted many exercises in the last year — all highly classified. But for cautionary warning, one only has to look back at a series of wargames held some two decades ago titled Millenium Challenge. That 2002 series might have been what John Ratcliffe, current director of the Central Intelligence Agency, and Vice President JD Vance were aware of when they opposed aspects of this new war by Trump. Vance said it was a bad idea, according to reports, and Ratcliffe termed expectations of a popular revolt in Iran “farcical.” Yet Trump, under the heavy influence of Israel’s Netanyahu and the success of the June 2025 bombing, figured it would be a slam-dunk.
That may sound familiar. That’s what the then CIA director told President George W. Bush before the invasion of Iraq in 2003 — which led to one of the most disastrous strategic mistakes in modern U.S. history — one that strengthened Iran.
And guess what country prevailed in Millenium Challenge, the most expensive wargame ever held? Using mines, small boats, motorcycles and missiles, a “Red team” (Iran) succeeded in defeating the far more powerful U.S. forces. The “enemy” defeated the U.S. team, sinking an entire American battle carrier group and killing many American troops despite vastly superior U.S. forces, more advanced weaponry and technology. Held a year before the invasion of Iraq, the wargame was designed to demonstrate that American technological supremacy could overwhelm any adversary. The Red team’s asymmetric warfare, similar to Iran’s tactics this year, prevailed, shocking the Pentagon brass.
It is too soon to reach any clear projection of the outcome of this war in Iran. While the U.S. military has performed its appointed task effectively, while the effort to change the behavior of a murderous regime in Iran warranted tough measures to reverse, the political and world-wide economic turmoil has been extremely costly — an estimated $1 billion or more per day just for the U.S. Wars, as so many leaders have chimed, are easy to start but without any control of their consequences.
What is clear to me is that Trump has no clue of that truth. Given his lack of history, lack of military experience and refusal to accept wise counsel, I believe he is the most capricious, rudderless and reckless president in American history. And guess who warned us all of that 10 years ago when the former real estate dealer first ran for president.
Fifty of the most respected and experienced Republican leaders in national security and intelligence, signed a statement in 2016 that Trump would be “the most reckless president in American history.” Trump, it said, “lacks the character, values and experience” to be president, “and would put at risk our national security and well-being.”