Two weeks to stop the war: Trump’s trepidatious Iran timeline

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President Donald Trump said last month that the war in Iran would be over “within two weeks … maybe three.” Yet, with the regime still intact and unwilling to give up nuclear enrichment, it seems things are just getting started.

The Trump administration’s Iran war timeline feels a lot like the COVID-19 lockdown timeline. “Two weeks to stop the spread,” they said, yet lockdowns and mandates persisted for months or years; some places still haven’t recovered. Similarly, we have been hearing for nearly two months that the war is about to end — yet War Secretary Pete Hegseth just warned on Thursday that the United States is “reloading with more power than before” and White House Deputy chief of staff Stephen Miller recently said the war could continue “indefinitely.”

After launching Operation Epic Fury, Trump said the bombings would continue “throughout the week.” Two days later, he projected a timeline of “four to five weeks.” The next day, Hegseth said, “It could be three” weeks or as high as eight. The following week, Trump said the war would be over “very soon.” He said on March 9 that “We’ve already won,” and on March 11, he said the war would be over “soon” because there is “practically nothing left to target.” The next day, he said Iran was “pretty much at the end of the line.” He declared victory once again on March 24 and March 26, saying “we’ve won this war,” and “they’re defeated.” And this week, he said the war is “very close to being over.”

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And yet the regime, while battered, is still standing, continuing to commit war crimes and domestic atrocities. Coming full circle, Trump said a couple of weeks ago that the war was ending “very shortly … We’re going to hit them extremely hard over the next two to three weeks.”

Trump’s two-week timelines don’t stop with Iran; he’s made similar projections regarding the Russia-Ukraine war, the proposed acquisition of Greenland, the Israel-Hamas war, the TikTok deal, and various trade deals.

I fully support Trump’s move to strike Iran. I think it would be suicidal to allow the regime to obtain nuclear weapons and create a jihadi North Korea crisis. The conflict also significantly weakens China, by far Iran’s largest trading partner and our greatest adversary. But while Trump understandably wants to maintain flexibility over his timeline, his projections repeatedly undercut his “we won” messaging. And while I acknowledge the value of strategic rhetoric and public posturing, I wish we had more clarity from the White House, because the war is driving up costs that impact us all. Those costs may also be a factor in Trump’s ever-changing timeline and repeated declarations of victory, as he attempts to soft-launch an unpopular long-term conflict that we’re paying for through taxation and inflation just months before the 2026 midterm elections.

Whether or not regime change is the best solution in a vacuum, ending this war without toppling the Iranian regime would be extremely dangerous. The people who chant “death to America” and call us “the great Satan” will be even more radicalized if they’re allowed to stay in power.

A February piece in the Foreign Affairs magazine, by the Council on Foreign Relations, argued that the way to enact regime change in Iran without putting troops in place would be to weaken it enough that the Iranian people could “do the rest.” The U.S. and Israel have killed Ayatollah Ali Khamenei and a slew of other top political and military figures, annihilated the country’s navy, and damaged or destroyed the vast majority of its defense industrial base, production facilities, launchers, and stockpiles. Yet the Iranian people are either unwilling or unable to finish the job from the inside.

Did Trump think doing 80% of the job would force the regime to give up? As the ceasefire deadline gets closer, it does become more probable, but as it stands now, Iran seems emboldened. With over 50,000 U.S. troops in the region, in addition to other military assets, Trump has three options: Give up and allow a more radicalized regime to regain its strength, strike Iran’s civilian infrastructure to put more pressure on its leaders, or conduct a ground invasion.

The ground invasion option is most likely to accomplish all of Trump’s objectives for the war, but would certainly cause the most loss of American lives in the process. Striking infrastructure could cause the regime to buckle, but they appear to be suicidally determined to continue fighting, similar to Japan at the end of World War II. And throwing in the towel would look terrible for Trump, no matter how he tries to frame it, because at the end of the day, we will have only set Iran back temporarily while further radicalizing them.

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The first 80% of the job was easy. The last 20%, should we choose to finish it, will likely take more time and manpower than the rest combined. That’s not going to be popular during the midterm elections, and it’s definitely not going to drive down the cost of oil. Trump is in a pickle right now, but if anyone can get out of it, I believe it would be him.

With peace talks going nowhere and the ceasefire winding down, the only thing that can be sure is the two weeks to stop the war, much like the “two weeks to stop the spread,” will last a whole lot longer than a fortnight.

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