Don't Do Stupid Shit: A Foreign Policy Doctrine Nobody Can Follow
Four words of Obama-era wisdom turn out to be the hardest advice in Washington to actually take, and Trump's Iran gamble is proving it the expensive way. Grab some popcorn — or better yet, hide it, because apparently even snacks aren't safe from geopolitical chaos these days.


DON'T DO STUPID SHIT: A PRESIDENTIAL PHRASE THAT TURNS OUT TO BE HARDER THAN IT SOUNDS
Somewhere in the multiverse there's a version of Donald Trump who took foreign policy advice from Barack Obama, and in that universe things are going great, everybody's relaxed, gas is cheap, and nobody's currently bombing anybody's uranium. Alas, we do not live in that universe. We live in the universe where Trump and Obama regard each other with the warmth of two cats forced to share one sunny windowsill, which means any advice Obama ever gave was automatically filed under "absolutely not," even the advice that was, annoyingly, pretty good.
That advice, as Obama once explained to a journalist, was the entire secret to running American foreign policy in four words: "Don't do stupid shit." This is not exactly the Gettysburg Address. It is the kind of thing your uncle says right before you attempt a home fireworks show, and it turns out to be timeless precisely because approximately nobody follows it.
Which brings us to Trump, who on February 28th joined Israel in launching a war on Iran with, and I want to be fair here, apparently no actual plan for what happens after the launching part. He reportedly suggested that killing off Iran's top leadership and unleashing a bunch of airstrikes would basically cause the Iranian government to fold up like a lawn chair and go home. Experts have compared this level of optimism to thinking you could bomb the Mafia out of Sicily, which, if you've ever met a Sicilian or watched approximately one episode of anything about organized crime, you will recognize as a plan with the structural integrity of a gingerbread house left out in the rain.
Now, in fairness to Trump, not everything on his Middle East report card is a disaster covered in red pen. The Abraham Accords — getting four Arab nations to recognize Israel — was a genuine, real, grown-up accomplishment, the diplomatic equivalent of getting four cousins who don't speak to each other to all show up for Thanksgiving. He also eventually strong-armed Netanyahu into a Gaza ceasefire, which, sure, took longer than it should have and things over there remain grim, but "eventually did the right thing after a lot of foot-dragging" is a category Trump doesn't usually even qualify for, so we should note it while it's happening.
Even the initial strike on Iran's nuclear sites last summer, risky as it was, at least followed something resembling logic — hit the nuclear program, degrade it badly, accept that international inspectors lose access to enriched uranium as a cost of doing business. Iran's muted retaliation suggested the strategy mostly worked. That's not "stupid shit." That's just regular high-stakes geopolitical shit, which is a different, more respectable category.
No, the stupid shit is the sequel nobody asked for: declaring victory-adjacent things about regime change with the confidence of a guy who's never once assembled IKEA furniture without extra parts left over. Iran is not a Roomba that stops working when you remove its head. It is a complicated, ruthless, deeply entrenched theocracy, and "we killed the leaders, so now it'll collapse" is the geopolitical version of thinking a chicken with its head cut off is definitely, for sure, totally done running around.
And speaking of things Trump wants that he absolutely will not get: Greenland. He keeps demanding to buy or annex it like it's a timeshare Denmark is being unreasonable about. Annoying Denmark, a NATO ally currently useful for the small favor of helping deter Russia, is not a great strategy, but it clears the bar of "merely unwise" rather than "stupid shit" — right up until the moment somebody floats an actual invasion, at which point congratulations, we've found the stupid shit, it was hiding in Greenland the whole time.
Here's the truly funny part, and by funny I mean darkly hilarious in the way only foreign policy history can be: Trump and Obama actually agree on a surprising amount here. Both wanted out of the business of babysitting the Middle East forever. Obama tried to "pivot to Asia," reasoning that America's investments would "yield the biggest returns" somewhere that wasn't a permanent regional bonfire, only to get sucked right back in by Syria's civil war and ISIS, like a guy who tries to leave a party and ends up back at the keg forty-five minutes later explaining why he's still there.
Trump tried his own version of the pivot, standing in Riyadh promising Arab leaders the region would soon be defined by "commerce, not chaos" — selling nuclear tech, defense systems, and AI instead of dropping bombs, while, in a detail that writes its own punchline, members of the Trump family personally picked up hundreds of millions of dollars from Gulf investment funds along the way. Nothing says "commerce not chaos" quite like the president's relatives cashing checks from the neighborhood you're simultaneously threatening to bomb.
Then, roughly five minutes after promising commerce over chaos, Trump delivered chaos. Turns out it's tricky to build billion-dollar AI data centers when Iranian missiles are landing in the general vicinity, a business insight so obvious it should be on a fortune cookie. Now the Gulf states are quietly doing what smart people do when the guy who promised to protect them also just personally insulted the crown prince of Saudi Arabia — bragging in public that MBS never imagined he'd be "kissing my ass" — which is not, historically, how you keep an ally feeling valued. They're hedging. Paying off Iran on the side. Cozying up to Turkey for defense deals. Flirting with China economically. In other words: the neighborhood is starting to look elsewhere for a landlord.
The lesson, four words long, remains stubbornly true no matter who's in the Oval Office: don't do stupid shit. It's simple. It's not partisan. It rhymes with nothing, which is probably why nobody remembers it in the moment. And if the last however-many months prove anything, it's that "simple" and "easy" are, once again, not the same thing at all.

Contact
Questions or tips? Reach out anytime.
contact@leeboy.us
© 2026. All rights reserved. LeeBoy.us LLC - Lee Murphy
