CROSSPOST: DAN DREZNER: The Trump Administration Strategy Fail
The Trump Chaos-Monkey Doctrine: how bluffing two adversaries at once backfires; “they have more to lose than we do” — and other things that aren’t even plans. When you skip the walking-down the game-theoretic strategy tree that planning is, your adversaries dig in and your former allies decouple. Both with force and at speed:
Dan Drezner is fed up with the Trump administration because:
Leverage without a plan is not strategy — and both adversaries are calling the bluff.
Assuming your opponent is about to collapse is a recurring, unforced error that forecloses realistic diplomacy.
Public trolling actively degrades bargaining position by hardening the other side and closing off cooperation.
Canada is not the weaker party it’s assumed to be; resource dependence cuts both ways.
The administration’s inability to recognize it’s losing means the losses will likely compound “through November.”
CROSSPOST: DAN DREZNER: The Trump Administration Strategy Fail
<https://danieldrezner.substack.com/p/the-trump-administration-strategy> <https://danieldrezner.substack.com>
They have no idea what they are doing in Iran or Canada.
Daniel W. Drezner
Sep 09, 2026 ∙ Paid
Have you heard the good word about the new U.S. strategy in Iran? The Wall Street Journal’s Shelby Holliday and Alexander Ward provided some details last week:
Trump has sent mixed signals on what might happen next. Trump has embraced an economic pressure campaign in recent weeks in the hopes of forcing Iran to the negotiating table. Tehran has shown no sign of backing down, however, and the U.S. and Iran continue to exchange fire as both nations assert control over the Strait of Hormuz. Privately, Trump is having discussions with senior aides about whether to declare the Iran war over, U.S. officials said, noting Trump has said he favors the idea. Trump also tells aides that he believes sticking with economic pressure will eventually force the regime either to dismantle its nuclear program or collapse, they said.
“I like our position now much better, with almost total control of the Hormuz Strait, and their economy totally collapsing,” he wrote on social media. “They are just playing out the inevitable. When are the Iranian people going to rise up and fight?”…. As Trump waits to see if his strategy will work, the U.S. military is maintaining a presence of 50,000 troops in the region in part to give the president flexibility on next steps. Current missions include intercepting Iranian missiles, providing cover for commercial ships in the strait and blockading Iranian ports and coastal areas. U.S. forces also stand ready to launch larger offensive attacks should Trump choose to escalate the war.
Now, if this feels a bit like déjà vu, that’s because we have been down this road multiple times — and yet Trump repeatedly fails to stick to this strategy for any appreciable amount of time. As I wrote back in May: “there are multiple reasons to be skeptical that ‘blockade and wait’ will work. The two most obvious problems have to do with Trump’s decision-making pathologies. As previously noted, Trump is lousy at playing a waiting game, and that’s what this strategy entails….. A second pathology is the administration’s wishcasting that Iran is just days away from collapsing.”
Meanwhile, the Trump administration’s approach towards its galactically stupid trade war with Canada appears to be to amp up the insults and the trolling. Secretary of Commerce Howard Lutnick and U.S. Trade Representative Jameson Greer added their own analyses last week, claiming that Carney had escalated the dispute for “political purposes”:
“It was manufactured,” said Lutnick, during a press conference in Washington on Thursday. “So there’s the sovereignty party trying to run, and they’re in the lead in Quebec and so this was Mark Carney manufacturing something that would try to keep them from winning, and then you have Alberta has an independence resolution.”…. Greer previously told CNBC on Monday that Carney’s claims that the U.S. was trying to curtail French protections was a “funny fake story.”
In that interview, Greer said Canada came back after a tentative deal was announced on Tuesday, wanting more than what the U.S. was prepared to give. “I don’t know if it was political for them,” he said. “It certainly doesn’t make economic sense, but perhaps for political reasons, they have some byelections coming up”…
This appears to be part of a larger attempt to sow domestic division within Canada. Now as I have noted previously in this space, the Trump administration’s foreign policymakers are so lazy that they keep self-sabotaging. And in the cases of both Iran and Canada, that self-sabotage is bearing some bitter fruit.
<https://danieldrezner.substack.com/p/the-trump-administration-strategy> <https://danieldrezner.substack.com>
Brad DeLong here: That is where Dan Drezner’s paywall kicks in. After it, there is an extended quote from Politico’s Nahal Toosi::
One strange aspect of the U.S. faceoff with Iran is that, in this modern age of advanced warfare, some basics have been forgotten. Stuff like: Make sure you have enough weapons. Keep your friends on your side. And clearly define your ultimate goal. Perhaps most important, though, is “know your enemy.” An awareness of your enemy’s strengths and weaknesses is key to figuring out how to defeat them. When it comes to the regime in Tehran, the Trump administration appears to still be in the early learning stages. A clear sign of this is administration assertions that Iran’s regime is splintered or so divided that it can’t even effectively negotiate. At times, President Donald Trump and his aides, including those who’ve negotiated with Iranian officials, seem frustrated or outright surprised by such dynamics….
When I ran the recent Iran developments by current and former U.S. officials and others who closely follow the Iran crisis, they generally agreed that the Iranian regime’s shape-shifting was business as usual. The bottom line for many was that the regime, having survived despite the assassinations of many of its top officials, appears solidly in control for now. The Islamic Revolutionary Guard Corps, a military body that reports directly to the supreme leader, has significant sway. Internal disagreements are about tactics, not strategy….
By overstating the regime’s divisions, Trump could be missing strategic opportunities. That’s especially true if the U.S. military and economic pressure campaigns don’t work and Trump decides to once again try diplomacy. To get to a deal, it will likely be critical to structure an offer that would pass muster with the pragmatists, the hard-liners and whoever is in between in Tehran…
Then Dan notes that the U.S., does not, in fact, control the Strait of Hormuz: “traffic across the strait is at its lowest level in months…. Peter Eavis and Jenny Gross report [that] Iran has been able to stymie U.S. efforts to re-open the waterway”:
Attacks from Iran have continued to deter many tankers from operating in the strait…. In the seven days through Thursday, a daily average of 6.7 million barrels of oil transited the strait, nearly 60 percent less than in the months before the war began…. Iran now wants to formalize its influence…by charging… fees…. Industry executives said they didn’t want to risk the lives of their crews or lose a vessel for weeks if it was struck. Most of the time, Iran’s attacks don’t destroy tankers, but some do enough damage that the ships are out of action while they are repaired…
Then Dan switches to Politico’s Zi-Ann Lum on how Lutnick on Canada is a real moron:
“I don’t think, with all respect, appointed, unelected Cabinet members in the United States are experts on Canadian politics,” Carney told reporters Thursday in Thunder Bay, Ontario. Carney, who urged the U.S. to “stop trying to be tough and start being serious” this week, said it was the Americans’ “our way or the highway, take it or leave it” attitude that made it clear the Trump administration wasn’t going to move on issues Ottawa viewed as red lines. “We’re ready to sit down and strike that deal when the Americans are ready,” he said Thursday….
Lutnick has maintained that at the last minute Canada demanded that trucks receive the same tariff relief as passenger and light-duty vehicles. Canadian negotiators said they’d been flagging the issue as a nonnegotiable since talks intensified in July. Chief U.S. trade negotiator Janice Charette told POLITICO that another red line was a concept floated by U.S. Trade Representative Jamieson Greer to have future Canadian free-trade agreements fall in line with the Trump administration’s policies…. The sides are currently not talking or making an effort to stop Canada’s countertariffs — a threat Trump Cabinet members have met with a shrug, focused instead on making the argument that the American economy is too big for Canada’s measures to have any impact…
Followed by noting that Canada can hurt the U.S. economy, quoting Politico’s Mike Blanchfield:
Canada is no longer talking about critical minerals as an asset to share with the United States, as it slaps back at the Trump administration in its bitterly escalating trade war…. Although Trump keeps insisting otherwise, the U.S. relies heavily on Canadian resources. Canada supplied more than 80 percent of U.S. electricity imports in 2025, according to the Canada Energy Regulator. U.S. Ambassador to Canada Pete Hoekstra has singled out potash as something America needs. Shortly after arriving in Ottawa in April 2025, Hoekstra told POLITICO that Trump was “very interested” in Canada’s energy and critical minerals.
Washington views Canada’s stockpiles as a bulwark against Chinese dominance of the global market in critical minerals essential to defense, quantum computing, artificial intelligence and virtually every piece of tech. Canada and the United States have a cooperation agreement on critical minerals that took root in the Joe Biden administration and continues under the Trump administration. After walking away from trade negotiations last month, Prime Minister Mark Carney signaled he was losing interest and patience in cooperating with the U.S. on critical minerals. He said he would continue finding deals and keep pursuing them elsewhere, suggesting Washington had squandered an opportunity to cooperate with Canada…
With Dan then summarizing:
It sure seems as though the United States is responding with dumb memes and own goals — almost like there really is no U.S. strategy as the trade war worsens…. Megan Messerly…. “I talked to a senior White House official about this last week, who actually said the Canada situation was ‘almost like Iran.’ The person told me: ‘They have a whole hell of a lot [more] to lose than we do.’” The problem, of course, is that the administration has no actual strategy beyond believing that they can employ their leverage to get what they want…. These are galactically stupid wars and will end badly for the United States. And the Trump administration is too witless to realize that they are losing…
What do I think of all these issues?
I agree with Dan that attempts at coercive leverage and public trolling as a substitute for actual planning is really stupid. Actual planning walks down the game theory strategy tree. Not doing so is (a) completely characteristic of the chaos-monkey Trump administration, and (b) unlikely to end well for the United States. The Trump administration’s creating an adversary and then automatically assuming that the adversary is fragile and near collapse (Iran’s regime “splintered”; Canada as the party with “more to lose”), and therefore waiting for capitulation is not how it works. So when the first round of pressure fails, no fallback plan exists.
Moreover, this form of attempted “diplomacy” teaches those you have made your adversaries three things:
You will start conflicts for no reason.
You cannot be counted on to understand and follow your own interests, so you cannot be counted on not to do things that are not just reasonless but completely self-defeating and deranged.
You are more focused on creating memes to make your domestic base happy than in actually running a, you know, foreign policy.
Even if a deal is reached, you will not keep it.
Therefore you, as a country whom Donald Trump has picked as an adversary, need to, first of all, decouple from the United States as fast as possible and completely as possible in order that Trump not even imaagine that he has leverage over you.
And that Trump’s term will be over in less than 2.5 years does not help: a United States that elected Trump president twice is too deranged to be regarded as anything but a roaming chaotic natural disaster.
Therefore you need, second of all, to figure out what pressure points you have that will make Trump kowtow to you the way he decided he needed to kowtow to Xi Jinping—and apply them.
That is too bad for the Americans who find themselves grist for the mill, but most of them did not care whether or not Trump became president, and among those who did more than half were pleased to support him.
And there are many such pressure points for (7). This is wise:
Paul Krugman: Adding Injury to Insult, Canada Edition <https://paulkrugman.substack.com/p/adding-injury-to-insult-canada-edition>: ‘This idiotic trade war will hurt more than people realize…. The derangement isn’t coming solely from Donald Trump…. He… [and] Natalie Harp… post… puerile insults and images on social media. But we also have Scott Bessent, the Treasury Secretary, comparing our northern neighbor to a “little yippy dog.”… Part of the job of being a finance minister involves projecting a certain gravitas…. When he sounds like an immature thirteen-year-old instead, that does real damage….
It’s also important to realize that an escalating trade war with Canada will do real damage to the U.S. economy…. Canada concentrates on producing a limited range of goods… some… [of which] take advantage of Canada’s natural resources… [and others produced at] economies of scale by… exporting most of what it produces to the United States while importing the auto models and components it doesn’t produce…. Canada supplies… 70 percent of the oil refined in the U.S. Midwest… 60 percent of US aluminum…. almost all of America’s spruce-pine-fir lumber… for framing in residential construction. If the tit-for-tat with Canada were to escalate into all-out trade war, could the U.S. economy manage? Yes — but it would be expensive and take a great deal of time…
Long run, this is such a complete disaster.