Will Iran Escalate As an October Surprise?

A couple days ago the Wall Street Journal reported that Iran was looking to escalate the war with America as part of a strategy to make continuing the fight more costly and difficult.

After President Trump signed a memorandum of understanding with Iran in mid-June, administration officials fanned out to build support for an agreement they hoped would reopen the Strait of Hormuz and start winding down the war.

Iran’s hard-line leaders huddled in Tehran and came up with a different plan, according to Iranian and Arab officials. In their view the pact was likely just an attempt by the U.S. and Israel to take pressure off the global economy and buy time for a bigger attack down the road. Instead of putting faith in talks, they took the past two months to prepare for a bigger fight…

Arab intelligence officials have picked up evidence—including communications between Iran and militia allies in countries such as Yemen and Iraq—of a strategic shift inside the country’s hard-line leadership to get their forces ready to widen the war and raise the costs for the U.S., officials familiar with the findings say. Alarming weaker Gulf countries like Kuwait, Iran’s leaders are increasingly talking about offensive operations on enemy territory.

Their overriding goal is to inflict enough pain to ensure the kind of attacks Iran has endured with the 12-day war last year and the continuing conflict aren’t repeated…

People close to Iran’s top negotiators have warned peace talks could be just an interlude before more conflict. Mehdi Mohammadi, a strategic adviser to chief Iranian negotiator Mohammad Bagher Ghalibaf, described the current stalemate Tuesday as the calm before the storm.

Iran doesn’t want peace. As they’ve said very loudly and repeatedly, they want Trump dead. And while murdering a U.S. president turns out to be pretty difficult to do, especially from the other side of the world, there are other things Iran can do to damage Trump. One of those, obviously, is to make sure his party loses the midterms.

Iran has a lot of experience with punishing U.S. presidents. The regime severely damaged Jimmy Carter’s chances of being reelected by kidnapping U.S. hostages and refusing to release them prior to the election. 

Today, Marc Thiessen has a column at the Post tying all these threads together. He suggests that Iran may be preparing for some kind of October surprise designed to do similar damage to Trump.

Though Trump did enormous damage during Operation Epic Fury — destroying more than 85 percent of Iran’s defense industrial base, sinking its navy, grounding its air force and annihilating its conventional military forces — he stopped about 14 days short of completely U.S. Central Command’s target list. This left Iran with enough firepower to threaten Gulf energy infrastructure, U.S. bases and the ships making “dark runs” through the strait.

Iran could decide to use that firepower before Americans go to the polls in November. One reason Trump has hesitated to resume major combat has been his stated concern that Iran might retaliate by launching attacks on energy targets in Saudi Arabia, Qatar and other Gulf states, taking much of their oil off the world market and sparking a global depression. As Trump explained, “I never want to be the late, great Herbert Hoover.”…

Iran believes that it is winning the battle of wills with Trump. As retired Gen. Jack Keane points out, Iran’s leaders may think that if they launch an attack before the midterms, “there’s a good chance that the Democrats will take control and maybe stop funding the war.”

Democrats retaking the House and/or Senate would damage Trump and would very likely help Iran directly as Democrats work to stop the fighting. Put another way, Iran and Democrats have the same enemy.

Thiessen’s conclusion is that Trump should finish the bombing of Iran now while he still can and force them to reconsider. At a minimum it might break up some of the existing plans. But of course there are reasons why Trump hasn’t gone all the way so far. The midterms are only a few months away and, at the moment, a substantial amount of oil is making it through the Strait of Hormuz, keeping energy costs from spiking. That could stop if Iran starts shooting everything that moves in response to a U.S. attack.

I don’t know if finishing the job now would work, but I do think Thiessen is right that Iran is probably planning some serious mischief over the next two months. By the time we find out what that is, it may be too late to do anything about it.

Editor’s Note: The 2026 Midterms will determine the fate of President Trump’s America First agenda. Republicans must maintain control of both chambers of Congress.

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