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Five Months In, and Still No Answer to the Only Question That Matters

A war that was supposed to last four to six weeks is now in its fifth month. Nightly bombings. Iranian drones striking US bases across Kuwait, Bahrain, Qatar, Jordan and Syria. Seventeen US service members dead. Brent crude again above $90 a barrel. And still, no end in sight.

This is not how it was supposed to go. On March 10, Trump declared at a military ceremony: “Right from the beginning, we projected four to five weeks”. By July, that prediction had become a cruel joke. The war has now dragged on for nearly five months, with no end in sight.

The administration has tried three strategies so far: regime change, relentless bombardment, then diplomacy. Each has come up short. Trump declared victory, signed a ceasefire, declared it “over,” bombed again, floated a 20% toll on ships using the Strait—then reversed within 24 hours. Trump appears to have put himself in a box.

The administration’s stated aims—regime change in Tehran, ending Iran’s nuclear program, curbing its military, and reopening the Strait of Hormuz—remain unachieved. The Strait was open to free navigation before the war. Now it is a battleground. Iran has effectively closed it to shipping traffic, and Trump is fighting to restore a status quo that existed before he started the war.

Meanwhile, the conflict has expanded dangerously. On July 17, Iran launched attacks across the Gulf region, targeting US military sites in Kuwait, Bahrain, Qatar, Jordan, Syria, Oman and Iraq. Two US service members were killed and one remains missing after Iranian ballistic missile and drone attacks in Jordan. Iran’s Supreme Leader Mojtaba Khamenei declared that America’s “repeated breaches” of the ceasefire had “laid bare a fundamental truth: the signature of the US president is utterly worthless and devoid of credibility”.

Trump’s latest gambit—a 20% fee on all vessels transiting the Strait—lasted all of 24 hours. He abandoned it the following day. This is not strategy. This is flailing.

Former Trump chief of staff Mick Mulvaney offered a grim assessment: “The war will continue now until the Iranians don’t want to continue in hostilities”. In other words, the end is not in American hands. It is in Tehran’s. And Tehran shows no sign of relenting.

I learned this lesson in Afghanistan in 2009, sitting in a NATO military meeting chaired by General Stanley McChrystal. Watching American officials speak with arrogant condescension about Afghan army efforts, it became crystal clear to me: the Afghans would win that war. Not because they were stronger, but because resentment builds. The “green-on-blue” attacks started shortly after. The rest, as we all know, is history.

The parallels are unsettling. America’s Gulf allies publicly distanced themselves before the war even began. Kuwait, Bahrain and Jordan have all come under Iranian fire, caught in a crossfire they never asked for. The joint investigations and statements of solidarity continue, but the trust is fraying.

Now, five months in, the same question haunts us: What is the endgame? POTUS still hasn’t answered. And until he does, every bomb, every death, every escalation is just more evidence that he is making this up as he goes. The Strait that was open before the war is now a war zone. The nuclear program he vowed to stop is still there. The regime he promised to topple is still standing.

Trump may be reluctant to escalate given the war’s unpopularity, rising energy prices, and the risks to US forces. His approval rating has fallen to 34%, returning to the lowest level of his second term. But backing down in the face of Iranian defiance could add to Tehran’s sense of leverage. He is trapped.

As one analyst put it, “This has turned into a war of attrition, and wars of attrition tend to go on for a long, long period of time”. The question is not whether Trump can start this war. He already has. The question is whether he can end it—or whether he has simply added another chapter to America’s long, sad history of Middle Eastern quagmires.