Ten days into President Donald Trump’s war on Iran, his Joint Chiefs Chairman Gen. Dan Caine trotted out a well-worn Pentagon aphorism: “No plan survives first contact with the enemy.”
Once the dogs of war are unleashed, it’s never entirely predictable how things will go, or possible to envision exactly how it will end.
Some wars seem to hold the promise of quick victory, but despite one side possessing an overwhelming military advantage, they devolve into quagmires.
Just ask Vladimir Putin.
Some wars begin with spectacular success, but end up being long, hard slogs.
Afghanistan in 2001. Iraq in 2003.
And then some wars look unwinnable, but then, suddenly, end in victory.
While countless pundits have opined that regime change cannot be achieved by airpower alone, the 1999 war in Yugoslavia is an outlier.
NATO won after a 78-day bombing campaign that suffered no allied casualties, employed no boots on the ground, and led to the overthrow of dictator Slobodan Milosevic the following year.
But every war is different and has its unique challenges, and the Iran war is a textbook example of how the next war is usually nothing like the last war.
Trump, his confidence in the prowess of the U.S military boosted by the clockwork precision of the commando raid to capture Venezuela’s Nicolas Maduro, saw in a weakened Iran a chance to end its nuclear ambitions once and for all.
Trump envisioned a short war, in which Iran would be quickly overwhelmed by a precise, but punishing air campaign, and have no choice but to agree to “unconditional surrender,” and a new leader willing to work with the United States.
When word leaked out that Caine, architect of the brilliant Maduro raid and last summer’s Operation Midnight Hammer attack on Iran’s nuclear facilities, warned Trump that Iran would not be an order of magnitude more difficult, given the lack of allies aside from Israel and the need for thousands of high-end munitions, Trump scoffed and slammed the “Fake News Media.”
“If a decision is made on going against Iran at a Military level, it is [Caine’s] opinion that it will be something easily won,” Trump posted on Truth Social five days before giving the order to attack. “He only knows one thing, how to WIN and, if he is told to do so, he will.”
Caine, by all accounts, stays strictly in his lane as senior military adviser, presenting options and outlining expected outcomes and consequences.
“I don’t make policy, I execute policy,” Caine said at a Pentagon briefing.
Trump had lofty goals for Operation Epic Fury, a name he personally chose — Iran’s military capability would be destroyed, the Iranian people would be able to overthrow what remained of the regime, 1,000 pounds of enriched uranium would be secured, and the threat of a nuclear-armed Iran would be forever ended.
So far, only the first goal seems to be on track.
“There was never any doubt that the United States military could obliterate the Iranian military, never a doubt,” Sen. Chris Van Hollen (D-MD) said on CNN. “The question all along has been for what purpose, to what end, at what risk, and what the hell is the endgame?”
Trump has been warned that Tehran’s response to any attack would be to widen the war, attacking U.S. troops and bases in neighboring Gulf States, and to close the Strait of Hormuz, the vital chokepoint through which 20% of the world’s oil flows.
But because Iran did not react that way in June after its nuclear sites were hit with bunker-busting bombs delivered by B-2 stealth bombers, Trump is said to have considered the chances of Iran blocking the strait or firing missiles at its neighbors to be unlikely.
“Nobody. Nobody. No, no, no. The greatest experts. Nobody thought they were going to hit. I wouldn’t say friendly countries. They were like neutral,” Trump said. “They lived with them for years.”
At a Pentagon briefing, Caine indicated that he had received no orders to make contingency plans for naval escorts to ensure the safe passage of oil tankers or cargo ships. “If tasked to escort, you know, we’ll look at the range of options to set the military conditions to be able to do that,” he replied to a reporter’s question.
Now that Iran’s threat to shipping has spiked oil prices worldwide, Trump is anxious to get the oil flowing again.
He appealed to Asian and European allies, and even to China, to provide ships for an escort mission.
When they turned him down, in a fit of pique, Trump declared the mighty U.S. military didn’t need help, only to reverse himself the next day and resume his criticism of NATO allies for not stepping up.
“President Trump has been basically offending all of these people and pushing them away, slapping tariffs on them, making it very clear that he doesn’t care about the partnership or the alliance,” said Rep. Adam Smith (D-WA). “They didn’t want any part of this war.”
Restoring commercial traffic through the strait is the current No. 1 priority, but it could take weeks as U.S. airpower seeks and destroys the sea mines, drones, and fast boats that Iran can use to threaten shipping.
Meanwhile, Trump has even bigger problems. The new ayatollah, son of the old ayatollah, is just as hard-line as his father, and is unlikely to want to negotiate with the U.S., given that his father, wife, and son were all killed in an Israeli airstrike that he barely survived.
“There’s no way you can say you won this war with an ayatollah in charge. No way you can say that,” said Sen. Lindsey Graham (R-SC), a Trump confidant. “If anybody like him is in charge, we’ve degraded their capability, but we have not gone to the source of evil.”
And then there’s the 1,000 pounds of 60% enriched uranium, enough to make 10 or 11 nuclear bombs.
“By all accounts, we don’t know exactly where it is located, and it may be buried and inaccessible,” retired Adm. James Stavridis, former Supreme NATO commander, writes in Bloomberg. “If the stockpile is accessible, it would undoubtedly be guarded by a significant Iranian force, probably the most elite units.”
Recovering that uranium would be a risky mission requiring U.S or Israeli ground troops, which Stavridis says makes it unlikely in the near-term.
War Secretary Pete Hegseth has bristled as news reports have suggested Iran is pursuing a “horizontal” strategy, seeking to spread the pain of the conflict to other countries.
“A fake headline that I saw yesterday, ‘war widening,’” Hegseth said. “Here’s a real headline for you, for an actual patriotic press: How about, ‘Iran shrinking, going underground’?”
While Trump has promised the war will be over in “the very near future,” reports suggest that thousands of U.S. troops may soon be sent to the region as the war enters a new phase.
“Even though Iran’s capabilities have been degraded a great deal, even though the United States and Israel have achieved major tactical gains, Iran still has the capacity to continue the war and basically not only to block the Strait of Hormuz, but also attack the global energy supply system in the Gulf,” says Fawaz Gerges, professor of international relations at the London School of Economics.
“Iran has widened the war. It has been attacking its neighbors because, as Iranian leaders have made it very clear, they want to increase the pain to everyone, including America’s allies and its neighbors,” Gerges said in an appearance on CNN.
“Military power on its own does not really make a difference. The war has shifted into economic pain, waterways, alliances, shipping lanes, and this is really where Iran’s strength lies.”
In other words, Iran is not trying to defeat the more powerful U.S. military. It’s just trying to survive.
As Henry Kissinger wrote about the Vietnam War in 1969, “The guerrilla wins if he does not lose. The conventional army loses if it does not win.”
There’s a famous anecdote about an American officer who was part of a U.S. delegation overseeing peace accords in Hanoi in 1975.
According to the New York Times, Col. Harry Summers remarked to a Vietnamese colonel that during the war, the Americans had never lost a single battle. The North Vietnamese colonel is said to have replied: ”That may be so, but it is also irrelevant.”
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In the case of Iran, the U.S. runs the same risk of winning every battle but losing the war.
It just depends on how much pain the Iranian regime is willing to endure.
Jamie McIntyre (@jamiejmcintyre) is the Washington Examiner‘s senior writer on national security.
