I've studied military strategy. Trump now faces Iran's oldest battlefield trick
War is not checkers. It is chess, a game that began in India and was refined and carried through Persia, where "shah" meant king and "shah mat" meant the king was helpless. The language matters because strategy, whether in chess or war, is not only about placing an opponent in check. It is about knowing how to finish the game.
President Donald Trump holds the stronger pieces, and Tehran knows it. That is why Iran is not trying to match America move for move. It is trying to widen the board before Washington decides how to close the game.
The pattern is now familiar. Trump strikes Iranian military targets. Iran pressures commercial shipping. Trump tightens the maritime noose. Iran threatens new energy routes. Each American move is answered not by matching American firepower, but by shifting the pressure somewhere else: at sea, in oil markets, across Gulf capitals and inside Washington's political debate.
U.S. Central Command has confirmed a fresh wave of strikes on Iranian coastal defense and missile sites, part of an effort to reimpose a naval blockade on Iranian ports and degrade Tehran's ability to threaten Hormuz shipping. Iran answered with strikes on U.S.-linked targets in Bahrain, Kuwait and Jordan, and with cruise-missile strikes that killed and wounded mariners aboard tankers in the strait. Tehran is trying to make each American strike produce a wider problem.
That is not simple retaliation. It is a counter-move, and Iran has used this approach before.
During the Iran-Iraq War (1980-1988), Tehran helped turn the Persian Gulf into a battlefield in what became known as the Tanker War. The U.S. Navy launched Operation Earnest Will to escort reflagged Kuwaiti tankers through the Gulf. In April 1988, the frigate USS Samuel B. Roberts struck an Iranian mine while on that mission. Four days later, the Navy answered with Operation Praying Mantis, sinking or damaging a significant portion of Iran's operational navy in a single day.
Iran did not defeat the U.S. Navy. It learned something else: mines, tankers, shipping lanes and oil anxiety can force a far stronger power to defend much more than a single waterway. That habit has not changed.
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The Strait of Hormuz remains the central square on today’s board. The U.S. Energy Information Administration reports that oil flow through Hormuz averaged roughly 20 million barrels a day in 2024, about a fifth of global petroleum consumption.
But Hormuz may no longer be the whole board. Reuters reports that Iran is signaling it could use its Houthi allies in Yemen to threaten the Bab el-Mandeb gateway to the Red Sea, putting a second vital energy artery at risk. Closing Bab el-Mandeb would force tankers around southern Africa, adding time and cost to global energy shipments.
A one-chokepoint crisis is dangerous. A two-chokepoint crisis becomes a test of American staying power.
Washington also handed Tehran an argument it did not deserve. Trump floated a 20% fee on shipping through Hormuz, then dropped the idea a day later, saying no one should be able to charge such a toll. The legal problem was obvious. The U.N.'s International Maritime Organization said there is no legal basis for mandatory tolls on an international strait under transit-passage rules.
America cannot credibly tell Iran it has no right to toll an international waterway while briefly weighing a toll of its own. Even withdrawn, the proposal was an unforced error.
The larger danger is that repetition becomes a substitute for strategy. Axios reports that Trump convened a Situation Room meeting to weigh an offensive wider than the current strikes near Hormuz, and Trump has said publicly that strikes on Iranian power plants and bridges could follow if Tehran does not return to the table.
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Force works when it narrows an enemy's options. It fails when it multiplies America's obligations. Tehran is betting that every American strike, threat and widened blockade will look like progress while adding another place Washington must defend.
Trump should refuse that bet. Three disciplines would help him do it.
First, stop making maritime policy in public. A major maritime policy should not reach a social media post before its legal basis, allied support and enforcement mechanisms are settled.
Second, name the war America is actually fighting. Is this limited retaliation, a maritime-security operation, coercive nuclear diplomacy or an effort to dismantle Iran's coercive infrastructure? Each answer requires different targets, different limits and a different explanation to the American people.
Third, use force to narrow the war, not expand it on Tehran's terms. American power should shrink Iran's options, not multiply Washington's burdens.
The Tanker War offers a caution. What began as a limited escort mission became a test of national will, alliance management and escalation discipline. Washington cannot afford timidity. It also cannot afford carelessness.
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Iran cannot defeat the United States directly, and it does not have to. Its strategy is to widen the board, raise the cost and survive long enough to call endurance a kind of victory.
Trump holds the stronger pieces. He has put Iran in check more than once this year. But check is not checkmate. A regime under pressure can still escape, counterattack and drag the fight into a costlier configuration if its opponent mistakes movement for strategy.
Trump has the pieces to prevail. What he needs now is the discipline to prevent Tehran from choosing the next square.