By Nick Catoggio
Tuesday, March 10, 2026
Yesterday I speculated that the White House had no Plan B
for the war in Iran because it
didn’t expect that it would need one. I imagined the president thinking
this was going to be another Venezuela, dopey as that may seem: “Neutralize the
country’s leader with an awesome show of force and wait for his terrified
deputies to sue for peace in hopes of avoiding the same fate.”
Last night the Wall Street Journal confirmed it. “Trump’s hope,
according to U.S. officials, was that the Feb. 28 decapitating strike on the
Iranian leadership … would trigger either a collapse of the Iranian regime or
the repeat of the Venezuela scenario, in which more pragmatic officials chose
to cooperate with Washington,” the paper reported.
It turns out that a regime of Islamist fanatics with
hundreds of thousands of men under arms wasn’t ready to surrender after a
single day of bombing. Suddenly everyone from congressional Republicans to Trump’s own advisers are praying for the mother of all
TACOs to end the war before an energy crisis swallows the GOP’s electoral
prospects whole.
What I didn’t get around to in yesterday’s piece is what
the price of a TACO would be. A creature as obsessed as Trump is with
projecting strength won’t easily stomach having to bug out of Iran with the
regime intact, its enriched uranium unaccounted for, and the Strait of Hormuz
still vulnerable to being menaced. MAGA zombies might buy his declaration of
“mission accomplished,” but no one else will.
A different kind of human would be chastened by a
miscalculation in Iran and rethink his hubris with respect to future military
adventures, but Trump will probably become more hubristic. Haunted by
appearing “weak” after failing to impose his will on the mullahs, he’ll scan
the global schoolyard for a pipsqueak to dominate—ideally one whom his
constituents have been spoiling to punch in the face for a long time.
There’s no mystery who that’ll be. Cuba wants to make
a deal, the president crowed to reporters at a press conference on Monday.
When asked what that deal might look like, he replied,
“It may be a friendly takeover, it may not be a friendly takeover. It wouldn’t
matter.”
“Friendly takeover” was also the term he used to describe
his designs on Cuba late last
month. Since then, despite being in the thick of war with the most sinister
Islamist power in the Middle East, he’s brought up his next regime-change
target repeatedly in public appearances. Cuba is “at the end
of the line”; Cuba is the “next
one”; Cuba will be “easy,”
requiring no more than an hour or so of Secretary of State Marco Rubio’s time
to strike a deal assuring the island’s submission.
There’s even been some movement within the Justice
Department to charge Cuba’s leaders with federal crimes, which you may
recall was the pretext for having U.S. troops capture Nicolás Maduro
without authorization from Congress.
Why Cuba? Why now?
A ripe target.
Well, for starters, the regime there really is at the end
of the line.
It’s been near the end for 67 years thanks to the
economic miracle of communism and a deathless U.S. embargo enforced by
presidents from both parties, but Trump’s Venezuela excursion has at last
pushed it to the brink. Without cut-rate crude flowing in from the now
Maduro-less government in Caracas, Cuba’s economy is in total collapse.
There are reports of locals picking through trash to find food,
losing running water in their homes, and doing chores in the middle of the night because that’s the only time of
day when electricity is available to power appliances. This week a CNN reporter based in Havana told of Cubans complaining to
him that “we have returned to the Stone Age” and that they can’t feed their
families. “Let the Americans come, let Trump come, it’s time to get this over
with,” one whispered.
Forcing Venezuela to turn off the oil tap to Cuba was a
brutal hardball gambit by the White House, but it achieved its intended
purpose, forcing Raul Castro’s grandson and caretaker into private talks with Rubio about the future of the regime.
That’s one answer to the “why now?” question: Cuba is “next” because it’s a
hostile power in America’s backyard that’s never been more vulnerable than it
is at this moment, especially with its friends in Moscow otherwise preoccupied.
As for “why Cuba?”, Trump himself supplied the rationale
at a public appearance yesterday. “No other president can do some of this sh-t
I’m doing,” he boasted to the crowd.
It’s very important to him, I think, to be
remembered as a president who did sh-t no other president could do, from
small-ball stuff like smearing his brand all
over the Kennedy Center to world-changing matters like helping Israel
assassinate the supreme leader of Iran. The common thread in his turn towards
militarism this year is settling Republican foreign-policy grudges that his
predecessors never forcefully addressed.
For years Venezuela’s Chavista regime agitated against
the United States, irritating the American right. Now its heir is sitting in a
U.S. jail and his successor takes orders from Washington. For years Iran’s
revolutionary regime waged proxy wars on America and Israel and stockpiled
enriched uranium intended for nuclear bombs, causing American hawks to warn of
an apocalypse if nothing were done. Now its uranium is buried under rubble, and
its leadership is dead.
The next, all-but-inevitable score to settle is with the
communists of Cuba, who’ve outlasted every U.S. president from Eisenhower to
the present day. They’re in Trump’s crosshairs not because he holds some strong
ideological objection to central economic planning—to
the contrary—but because he’s bent on succeeding where those who held his
office before him failed. He’s going to harpoon the great white whale that
eluded other American captains of state and impose regional U.S. hegemony at
last on the most unlikely and infamous holdout of the post-war era.
No wonder crazed hawk Sen. Lindsey Graham sounds like
he’s in the throes of religious ecstasy during his Fox News appearances
lately.
Sphere of influence.
There’s one more answer to the “why Cuba?” and “why now?”
questions, though. If Trump ends up humiliated in Iran, forced to cut the war
short to avert an economic disaster before his goals are achieved, I think he
might decide that he’s done with power projection outside the Western
hemisphere for the rest of his presidency.
His administration is already trending that way. In
January the Pentagon’s new National Defense Strategy de-prioritized the threat from China, a predictable turn to
those of us who long ago saw through nationalists’ phony
hawkish pretenses toward Beijing. And the president has no interest in
containing Russia, needless to say. (That’s the stark, unexplained exception to
his foreign-policy score-settling tour aimed at traditional Republican
enemies.) If and when the shooting finally stops in Ukraine, the White House
will almost certainly proceed to some comprehensive new rapprochement with
Moscow.
That’s why France is suddenly offering to create its
own nuclear umbrella for Europe. The era in which the United States
meaningfully deterred Russia is unofficially over already and will be officially over
soon enough.
As for the Middle East, I expect that it too will become
a no-go for an administration that’s bruised by its failure to subjugate Iran,
by the heat it’s taken from diehard “America First-ers” for waging another
regional war, and by polling that shows Americans turning against Israel.
Interventions there are too messy, too far-flung, and too difficult to be worth
the political trouble anymore.
Instead, I suspect, Trump will tend to his own garden by
focusing on America’s “sphere of influence” in its own hemisphere, where it can
menace military lightweights with little fear of resistance until 2029. That
means taking another run at Greenland eventually. (It’s
coming. Don’t kid yourself.) It means attacking Mexico’s cartels at some
point. And it most assuredly means dumping Castroism into the dustbin of
history.
Regime change in Cuba is an easy win relative to regime
change in Iran. But what would a “win” look like?
Delcy redux.
If the president had his wish, I think it would look like
Batista 2.0.
Fulgencio Batista was the strongman who ruled Cuba before
Castro’s rebellion toppled him in 1959. He was an s.o.b. (it was during his
tenure that Marco Rubio’s parents fled to the United States) but, as the saying
goes, our s.o.b. Batista was a U.S. client during the Cold War who made
Cuba a playground for American corporations and organized crime before the
economic resentment he sowed helped bring the communists to power.
He’s exactly the sort of character whom Trump
would like back in charge of the island, I suspect. Who is Delcy Rodríguez,
after all, if not a sort of Venezuelan Batista?
The president will want three things from a new Cuba.
First, of course, is a leader who does his bidding unquestioningly. Second is
an island economy that American businesses are free to colonize—after earning
the president’s favor on an ad hoc basis, of course—and a Riviera where rich
American tourists can frolic. (Remember how Gaza was teed up to become the Riviera of the Mediterranean? Wait until the Trump
Havana Hotel and Casino opens in 2028.) And third is a government that will
keep the population quiescent as the great redevelopment project commences.
An iron fist for Cubans and a velvet glove for Americans:
That’s the White House’s dream candidate to lead post-Castro Cuba. Batista 2.0.
But where can they find someone like that? They’ve been
looking for months within the regime for a Rodríguez-type who might be willing and able to fill the
role but without luck, as far as I’m aware. And maybe that’s no surprise:
As one Obama-era official explained to the Wall Street Journal, Cuba is
far more repressive and Stalinist in its indoctrination tactics than even
Venezuela is. “There’s nobody who would be tempted to work on the U.S. side,”
he predicted.
That would also complicate American operations to remove
the regime by force. “When you have a police state populated by people who have
no future in a pro-American successor government, they have no incentive to
give up, and they have the monopoly on firepower,” one historian warned The Atlantic of Cuba. That apparatus is diffuse and
decentralized too: “Even more than [Venezuela and Iran], Cuba's revolutionary
police state has been embedded and threaded throughout the country on a
literally block-by-block level,” Reason’s Matt Welch explained.
It’s the same problem the U.S. faces in Iran. Having
easily liquidated the Ayatollah and his top commanders, the White House is now
at a loss as to how to dislodge the vast Islamic Revolutionary Guard Corps that
actually runs the country.
But it gets trickier. In addition to being a nonstarter
for Cuba’s Castroists, Batista 2.0 might be a nonstarter for anti-Castroists
here in the United States.
At the risk of being naive, I doubt Americans will
tolerate strongman rule by “our SOB” on the island as easily as they’re
tolerating it in Venezuela. Cuban expats and their descendants haven’t spent 67
years calling for another Batista, they’ve spent it crying out for Cuba
libre. After generations of oppression and immiseration, the Cuban people
deserve real freedom—human rights, of course, and democratic elections. The
moral pressure on the White House to deliver it if the Cuban leadership
abdicates will be much greater than it was after Maduro was snatched from
Caracas.
And that could work out for the president. If
elections were held (er, somehow without the remnants of the Castroist police
state interfering), Cubans might plausibly elect a pro-American candidate in
the belief that a Trump-friendly leader would be better positioned to secure
economic aid from Washington. But there are no guarantees: Decades of communist
brainwashing and grievances about the U.S. embargo might produce a winner who
refused to be a White House puppet. And even if a pro-American candidate
prevailed, that person would serve two masters—not just Trump but the voters
who elected him or her.
That’s precisely why the president is in no hurry to hold elections in Venezuela. The moment a
new leader answerable to the people is chosen, he loses his marionette.
So what’s a mafioso who yearns to rule Cuba by proxy to
do? How does he install Batista 2.0 in Havana without tearing Castro’s police
state up by its roots and without angering the Cuba libre cohort
here at home?
Patience.
I don’t know how he does it successfully, but I think I
know how he plans to try. He’s going to solve the problem of how to replace the
Castroists by … not replacing them.
A few days ago USA Today reported that an economic deal between the
U.S. and Cuba is in the works and could be announced soon. “An agreement could
include a relaxation on Americans' ability to travel to Havana,” the story
alleged. “Discussions have included an off-ramp for President Miguel
Díaz-Canel, the Castro family remaining on the island and deals on ports,
energy, and tourism. The U.S. government has floated dropping some sanctions.”
A “friendly takeover,” we might call it.
The “off-ramp” for top officials could mean many
things—exile, amnesty from prosecution, or simply stepping down with assurances
that they won’t be targeted—but it sounds like the broader strategy is to open
up the island economically and hope that the infusion of cash proves so
intoxicating to the Castroist police state that its members decide to play ball
with Trump.
Is it likely that a vast Stalinist KGB will opt to go
straight and begin acting like normal peacekeeping cops? It is not. But I
assume that the White House will push a lot of money at them under the table to
try to secure their cooperation or, failing that, to entice them into
emigrating from the island.
It wouldn’t be regime change as much as it would be
regime co-optation, in other words, but with an extra degree of difficulty than
the U.S. faced in Venezuela. In that case, Trump left the Chavistas in place
without asking them to renounce their ideology; in this case, he’d be trying to
bribe America-hating communists en masse into supporting a new pro-American
capitalist regime.
“But the Cuba libre faction in the U.S. won’t
trust having Castroist thugs keep order in a post-Castro country,” you might
say. Are we sure about that?
If they can be convinced that the only way to achieve
long-term freedom for the Cuban people is to do so in stages, with the first
step involving economic liberalization to improve the dire standard of living
on the island, they might be amenable. And I know just the guy to convince
them.
“Cuba needs to change. It needs to change, and it doesn’t
have to change all at once. It doesn’t have to change from one day to the next.
... Everyone is mature and realistic,” Marco Rubio said last month. “They need to make dramatic
reforms, and if they want to make those dramatic reforms that open the space
for both economic and eventually political freedom for the people of Cuba,
obviously the United States would love to see that,”
The most credible member of Trump’s Cabinet, himself the
son of Cuban exiles, is on the verge of a diplomatic breakthrough that might at
last end Castroist rule in that country and send the country’s president into
the sort of luxe Moscow retirement that Bashar al-Assad is currently enjoying.
All he’s asking from Americans who are cheering on the effort is patience.
It might look initially like Batista 2.0, with plenty of
thugs weaned on Castroism still in positions of influence, but only as a
transitional point toward Cuba libre. That’s the ask. Patience.
Castro-haters aren’t the only ones capable of patience,
though. Delcy Rodríguez appears to be waiting the White House out on matters like elections and
severing ties with Russia and China, while making Trump happy on higher
priorities like oil. By next year Democrats might be back in charge of Congress
and/or by 2029 back in the White House—and an America where Democrats wield
real power will be one that’s less willing to compel Caracas to carry out its
wishes.
Cuba’s Castroists might take the same approach. If
Washington wants to bail them out of the economic calamity in which the island
is mired in exchange for their cooperation on “liberalizing,” they’ll take it …
and then, when the president is no longer in a position to threaten them,
they’ll reassert their authority by cracking down.
It’s less a question of whether we end up in the long run
with another strongman in charge there, in other words, than how willing that
strongman will be to work with the United States. That may not be Marco Rubio’s
dream for Cuba. But it’s probably the realistic best he can do.