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So what's the October Surprise?

A Trump surrender to Iran isn't out of the question, but it probably wouldn't help much.

8 min read

Via the latest Bluesky mini-meme, we learn that apparently punditguy Mark Halperin is still around—who knew?—and apparently everyone in Republicanism is texting him to tell him how bad internal polling is for Republicans, because apparently if you're a 2026 Republican election operative seeing new polls that suggest voters are going to feed your candidate to a wood chipper in November the first thing you do is dig up Mark Halperin's phone number to let him know that.

Sure, whatever. At this point I'm willing to believe that all of Republicanism is just one big text chain pity party. It'd still be more plausible than all of Republicanism being one big national security-compromising Signal chat or one big extremely disturbing sex & drugs club—and we know those two are true, so we'd look pretty ridiculous claiming the first one can't be.

Anyway: Don't care. Don't have to. Can't make me. But there was a completely useless tidbit in there that piqued my interest:

Efforts to get an October Surprise deal with Tehran are almost certainly an illusion and a trap for a dozen reasons, including the inconsistencies of U.S. "allies" in the region about what they want.

That's the punditguy's evaluation. It follows on the heels of a new proposal by Iran to reopen the Strait of Hormuz anytime Donnie wants.

Iran has offered to reopen the Strait of Hormuz and resume talks on its nuclear program in seven days if the United States lifts its naval blockade, waives sanctions on Iranian oil sales and observes a ceasefire that would include Lebanon.

That should sound familiar: It's near-exactly the same proposal Iran has put forth since the beginning of Trump's war. They agree to stop holding world oil supplies hostage (though possibly with new tolls imposed on Hormuz traffic) if the U.S. military agrees to pack up and go home, and the Israeli military agrees to leave Lebanon alone, and Trump drops sanctions on Iranian oil.

The AP's report doesn't mention U.S. reparations to Iran for the damage done by the attacks; it's not clear whether that demand was truly dropped, overlooked, or would be part of the "nuclear" negotiations being offered afterwards.

In any event, it would represent a humiliating defeat for the United States. The U.S. has already been driven from its military bases around the Persian Gulf after successful Iranian strikes; the relationship between the U.S. and its Middle Eastern allies is far shakier, now that U.S. security guarantees don't look so secure; Iran's control over the Persian Gulf would be solidified for the indefinite future; Iran would get an end to economy-crushing sanctions and have to give up, realistically, no more than what they'd already given up in the Obama-era nuclear agreement that Donald Trump tore up.

And, vitally, the U.S. proves itself the same sort of paper tiger that Russia is now considered: once a superpower, now unable to bring a far smaller and less capable foe to heel.

But there's never going to be a U.S. win here. The defeat is already baked in. Trump's not going to launch a ground war in Iran because the casualties would be horrific. There's no scenario in which Iran gives up its control of the Strait without concessions, and no non-ground-war scenario by which the U.S. can reopen it by force. It's been over half a year and Trump is still stuck, in his head, between the knowledge that his attack on Iran was a failure and a mostly-delusional hope that if he can maintain the status quo long enough, an unexpected miracle will fly out of his butt.

But now the midterms are here, diesel fuel is hitting $9 a gallon in many markets, farmers are irate, there's a 50-50 chance that Republicans lose both the House and the Senate, and if that happens the ability of Trump's various minions to f--k around on the taxpayer dime shrivels dramatically. There's no more wishing for miracles. Time's up.

So I actually think there is a non-zero chance Trump simply surrenders here. Takes his ball and goes home. Accepts whatever conditions Iran wants to impose on the United States, comes away with the thinnest possible promise from Iran that they won't drop a bomb on the U.S. mainland in the next few years, and declares Glorious Stupid Victory on the national airwaves in an effort to convince his voters that they can put away the wood chippers and vote for his Republican accomplices again.

You have to remember the core premise of Trump being Trump: He truly, sincerely does not give a shit about doing damage to America. He doesn't care. He considers the country to be nothing more than a stage on which he can build new monuments to himself, and he doesn't actually give a crap whether Iran controls the Middle East or has a nuclear weapon or any of the rest of it.

He wanted to bomb somebody because his military kidnapping of the Venezuelan president went great and he liked the feeling. He wanted to look tough. Now it's not fun anymore and he's looking for the next thrill, and to hell with the rest of you.

The U.S. Army Reserve is examining whether it can provide the military's Southern Command with police forces, medical personnel and other support units within the next four months, according to an internal Army message reviewed by CBS News.

Though the message makes no reference to Cuba, the request is for continued military planning aimed at Cuba, according to multiple U.S. officials who spoke to CBS News under condition of anonymity because they were not authorized to speak publicly.

That's CBS News reporting that the Pentagon is now planning out scenarios for a large-scale military operation in Cuba that would take place "possibly" in "90-120 days," and that whatever they're planning is in fact so large-scale that they envision needing to call up the Army Reserve to provide additional police and medical personnel.

Among the units is a combat sustainment support battalion that specializes in coordinating logistics such as transportation, maintenance, fuel and supply needs, along with an engineer battalion. The document also seeks an expeditionary sustainment command that would oversee logistics across a theater of operations.

This isn't no naval blockade they're planning for. It's an on-the-ground action needing supply lines.

Wonderful. Outstanding. Couldn't be worse.

From this, then, we can deduce that Trump and his Secretary of State(?) Marco Rubio have not lost their interest in toppling the Cuban government through military force. Even after their grand Iranian adventure ended in abject failure by every single metric, they still want another regime change-premised war.

That's not to say it will actually happen. But it's at least being planned for to an extent that the Pentagon is sending out requests for hard readiness numbers from the U.S. Army Reserves, and that suggests major ground operations, and that suggests major naval operations to get all those troops in-theater ...

And that, all together, means that the dwindling supplies of anti-missile missiles, our put-upon aircraft carrier groups, and all of the rest of it will have to be rerouted to the Gulf of Trump to stage attacks on another regional power, this one with the ability to conduct missile strikes on the U.S. mainland when Pete Hegseth f--ks it all up.

Trump and Rubio are bored with Iran. They don't want to be there. There's no upside there. They want to play with a new toy, not the one they broke. And, above all, all of these people are sociopathic idiots who don't particularly care whether the outcomes of their actions are good or bad so long as they feel good and testosteroney while they're doing it.

Any claims that Donald Trump is not thinking of staging a quick October surrender to Iran in a bid to (1) calm incandescently enraged Republican voters and (2) prepare for a new Rubio-led adventure down in Cuba are ... I don't know, fellas. I think you need to rack your pundit-brains a bit harder on this one. You're still thinking any of this has to do with logic, rather a dementia-addled narcissist's urges of the moment.

So I do think Trump might try for that October announcement, yes. And Iran knows he wants it, which is exactly why they're re-upping their proposal for a deal that gives Iran nearly everything it wants and gives Trump just enough of a face-saving "nuclear" deal for his Fox News prostitutes to paint as a victory.

I do not think it would make a damn bit of difference in the actual midterm vote totals, because six weeks is not enough time to unscrew global oil supplies. He waited too long, prices are too high, and voters are too ticked off. Right now the Trump administration is on a tear to try to patch up diesel markets, oil markets, and beef markets as their top-three Republican pain points, but they have stupided themselves into a corner. It's not clear they can double-stupid their way back out again.

The bigger "October Surprise," if we get one, is probably going to be the oligarchs pulling out all the stops to lie to voters. Big lies. Expensive ones. Think "the schools are making your child pee in a litter box" lies delivered to every swing district and swing household in America—to the tune of nearly $2 billion worth of rich asshole money.

Most of the money is coming from the usual culprits, from Musk to Uihein to Andreessen, all of it earmarked to protecting their own fortunes and turning the U.S. into a Russian-style kleptocracy. That's what's paying for the incessant focus on "trans kids" on the airwaves and in your mailboxes. It follows the usual conservative election pattern of finding and demonizing some already-marginalized group, creating an artificial panic with outright lies, all of it meant to fill up the discourse so that there's no time left to talk about gas prices or unprecedented corruption or how many of Donald Trump's closest allies appear in the Epstein files still being withheld from Congress.

Migrant caravans! Drug cartels might be working with terrorists for some reason! Barbaric immigrants are eating your pets! This time around, it's "if we don't check the genitals of every last youth soccer player, America will crumble."

That's an odd choice, in this Epstein-riddled environment, but they have half a century of experience in running orchestrated hate campaigns so they clearly have focus groups telling them it'll work. But it hasn't worked so far, because as much as hate-filled people like to hate immigrants and children they really don't like paying high prices at the gas pump. They do try, though, and they'll keep trying.

We also face the same problem we faced in 2024: The media, now fully under the control of the aforementioned oligarchs, is in the tank for Trump's white nationalist agenda. Nobody's even pretending otherwise at this point, and they will continue to chase after whatever jingling bell Republicans ring. They will continue to brush off Trump's most flagrant acts of corruption with headlines calling it merely "upending norms."

That's why every journalist in America thinks it's really, really important to get every Democratic candidate in America to weigh in on some attention-seeking Twitch streamer, and why there is no similar questioning of why Republican candidates can be plied with money from Nazi-saluting open white nationalist Elon Musk.

So we'll see. I'm a cynic by nature, and in my defense LOOK AROUND, and I do think that Americans are largely gullible enough to feed their own children to wolves if the wolves promised you'd never again have to meet a bilingual person. But this House and Senate have proven themselves so inept, so indifferent, so smarmy, so grotesque that we've seen even low-information voters recoil in disgust.

I don't think there's any October Surprise that can make much of a dent in that.

Hunter Lazzaro

A humorist, satirist, and political commentator, Hunter Lazzaro has been writing about American news, politics, and culture for twenty years.

Working from rural Northern California, Hunter is assisted by an ever-varying number of horses, chickens, sheep, cats, fence-breaking cows, the occasional bobcat and one fish-stealing heron.

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