Iran, Cuba, Trump.
It’s passing strange, politically speaking, that President Trump has chosen to bring the United States to the brink of war, or something like that, in the Middle East. The president knows his political base. He knows what they will abide and what they will not. And he knows that they will not abide a war in the Middle East.
What they might or and perhaps will abide is some kind of “decisive” strike against the Iranian regime; one that disables some of its ballistic missiles or destroys parts of its nuclear program or forces its leadership to negotiate some sort of deal that constrains their ability to wreak havoc in the region and beyond. But that’s it. Any suggestion of “mission creep” is a non-starter. Any over-long stay is a betrayal of Trump’s solemn promise of no more foreign adventures.
Iran knows this too. So, strategically-speaking, it needs to do everything in its power to rope-a-dope the United States: “Hit us again, harder and harder, until you’ve exhausted your available resources and the patience of your political base. And then you’ll have to retreat and we will have defeated the Great Satan again.” That’s the general idea.
And the way to do that is to take the initial (presumably heavy) hits and respond in such a way (attacks on U.S. bases, Saudi oil facilities, Israeli military installations, foreign embassies, etc.) that sucks the U.S. deeper into something like war. Not “boots on the ground” war, but “ladder of escalation” war; one that soon involves other regional powers, including (especially) Saudi Arabia, and turns days into weeks and weeks into months. The deeper the U.S. gets sucked in, the sooner support for “Trump’s war in the Middle East” will collapse (in the U.S. and amongst its allies in the region).
Here’s something you never imagined you would read on the “front page” of one of the nation’s leading newspapers:
The Pentagon is raising concerns to President Trump about an extended military campaign against Iran, advising that war plans being considered carry risks including U.S. and allied casualties, depleted air defenses and an overtaxed force.
The warnings have largely been voiced by Gen. Dan Caine, the chairman of the Joint Chiefs of Staff, within the Defense Department and during meetings of the National Security Council, current and former officials said, but other Pentagon leaders also have noted similar worries.
Such discussions are always part of the contingency-planning process before military operations, some officials said, noting that military leaders—especially the Joint Chiefs chair—provide prudent estimates of possible casualties and other potential costs of military operations.
Options being studied for strikes on Iran range from initial limited strikes to a days-long aerial campaign aimed at toppling the regime. All options carry risks, but a prolonged campaign in particular could incur significant costs to U.S. forces and munitions stockpiles, officials said, complicating the protection of regional partners if Iran is able to retaliate. If the U.S. uses up large amounts of air-defense munitions and other items that are in limited supply, it could also impact preparations for a possible future conflict with China. (Source: wsj.com. Italics mine.)
This story was sourced from (and by) the Joint Chiefs of Staff and its chairman. It didn’t arise from a couple of generals musing upon a major military campaign with three reporters from The Wall Street Journal who happened to be hanging around the parking lot. It was a concerted (and perhaps desperate) attempt to try to alter the course of events in the Middle East before it was too late.
It was aimed at the president, obviously, but also at his network of friends, his advisors, members of Congress, major donors, anyone who might have Mr. Trump’s ear. And to make sure the message got through, the Chairman and the Chiefs didn’t just “share” with The Wall Street Journal. The same story, more or less, appeared in The Washington Post and The New York Times, at the same time.
It’s not often that you get the Chairman of the Joint Chiefs of Staff practically begging the president to re-think his options regarding a major military operation on the front pages of three national newspapers. But there it was and there it is. We’ll find out soon enough if Chairman Caine was successful.
Which brings us back to what was (and is) “off” about all this. As a matter of national security (and American politics), Iran isn’t an urgent concern. Its regime is wobbling. Its economy is collapsing. Opposition to the regime is growing, all across the country. Push on those strings and who knows what might happen?
What won’t happen in that environment is a resurgence of support for Team Ayatollah. So why not adopt a kind of reverse rope-a-dope strategy? We’re not going to hit you as hard as we can until you fold. We’re going to wait and watch you do yourself in. To moves matters along, we’ll surround you with sanctions and make your life difficult in all sorts of different and annoying ways. And we’ll have more than enough military hardware in place to respond massively and immediately in the event you decide that the best defense is a good offense. So don’t make that mistake. In the meantime, good luck. You’ll need it.
Instead, we’re choosing to be impatient. It doesn’t make sense, militarily. And it makes no sense politically (at all). Especially because 90 minutes east of Key West, Florida lies the mother of all political opportunities: Cuba.
Cuba is on the brink of societal collapse. It’s hard to imagine the regime can survive for much longer. As a result, the United States has the opportunity to adopt Cuba as a kind of 51st state; a protectorate, if you will.
Sequence of events: The regime steps down (what choice does it have in two or three months, really?) and is replaced by an interim hybrid government (Cuban nationals, expats and U.S. advisors). In return, the U.S. pledges to underwrite vast investment in country. U.S. legal infrastructure (especially as it applies to commercial matters) is “installed”. The Cuban-American community floods the island with cash, development plans, energy and enthusiasm. Telecom companies rush to build out the island’s digital network; with fiber in the ground and next generation mobile everywhere above ground. New airports are built. Electronic vehicle infrastructure is built out. You get the drift.
All this would be a bonanza for the Cuban people. The unemployment rate would fall to zero. Tourism would explode. Commerce would explode. An enormous island of seemingly limitless possibility, now on the verge of economic death, would be reborn.
That’s a story easily sold. The banks and the i-bankers would love it. Corporate American would love it. The travel and hospitality “industries” would love it. The housing industry would be over the moon (“Havana condos”!). The Cuban-American community would at long last be able to return “home”. MAGA would have its big win. Trump would have done what no American president has been able to do since Eisenhower: “liberate” Cuba.
It probably wouldn’t win him a Nobel Peace Prize. But it does offer him the opportunity to create a 51st state. On terms that make sense and are beneficial to all concerned.
That would change the trajectory of the Trump administration or at least the
”substance” of its “political narrative”. The new story would be: America is growing again. There are new frontiers. Opportunities abound. Time-shares on all those amazing Cuban beaches. It’s a very MAGA sort of story; domestic foreign policy. And it sits reasonably well with everyone else.
Iran or Cuba? You’re a political advisor to the president: Pick one.
(How many beaches? If you overlay Cuba down on a map of the United States, its “coastline” stretches from New York to Chicago.)

