Obama Just Opened the Door for Castro's Spies
Cuban intelligence will have a field day in the United States thanks to
Obama's latest outreach to Havana
By John R. Schindler • 10/14/16 3:03pm
Normalization of relations with Fidel Castro's Cuba has been one of the
big foreign policy initiatives of Barack Obama's presidency. During his
two terms in the White House, Washington has overturned more than a
half-century's worth of American policies toward the Communist regime in
Calling that legacy a "failed approach," Obama's outreach to Havana,
particularly in his second term, has been pronounced, including a visit
by the president and the first lady to Cuba. By the time he leaves
office in three months, Obama will have substantially re-normalized
relations with the Castro regime.
Obama has pressed forward over the opposition of many Cuban-Americans
and human rights groups, who note that Washington's gifts to Havana have
not been reciprocated with greater respect for democracy and the rule of
law in Cuba, as many had anticipated. In the words of Amnesty
International, "Despite increasingly open diplomatic relations, severe
restrictions on freedoms of expression, association and movement
continued. Thousands of cases of harassment of government critics and
arbitrary arrests and detentions were reported."
Obama seems unperturbed by all this, and today he issued revised
guidance for the U.S. Government in its re-normalized dealings with
Havana. Presidential Policy Directive 43 is likely to be this
president's last push on Cuban matters, and its call to Congress to drop
the Cold War-legacy embargo on the Castro regime seems like to fall on
Most of PDD-43's guidance won't impact average Americans, unless they
happen to travel to Cuba. Obama has now permitted them to bring back as
much Cuban rum and cigars as they like—something Americans were last
able to do when Dwight Eisenhower was in the White House.
There's the usual Obama boilerplate about promoting democracy and human
rights in Cuba, though there's nothing in PDD-43 that seems likely to
make any impression on Havana. The document omits the word "Communist"
entirely. Cubans expecting this president to demand concessions from the
Castro regime in exchange for trade favors and diplomatic recognition
have been let down yet again by Barack Obama.
Some of PDD-43's guidance will have important national security
implications. It directs the Defense Department to expand its
relationship with Havana, especially in "humanitarian assistance,
disaster relief, and counternarcotics in the Caribbean." It further
orders the Pentagon to "support Cuba's inclusion in the inter-American
defense system…which will give Cuba a stake in hemispheric stability."
It's far from clear that Havana's Communist rulers—whose entire
worldview for more than a half-century has been based on resistance to
Yankee hegemony—actually want to be part of any American-led defense
apparatus in our hemisphere, but the Pentagon follows orders, so we can
expect the U.S. military to have more meetings and conferences with
Cuban counterparts at the table.
Perhaps the most curious aspect of PDD-43 is what it tells our
Intelligence Community to do. Obama has ordered American spies "to find
opportunities for engagement on areas of common interest through which
we could exchange information on mutual threats with Cuban counterparts."
That wording is intentionally vague, as spies like it, and it's not
clear if anything will come of it, beyond low-level information sharing.
Nevertheless, it's apparent that Obama is declaring a truce in the
SpyWar that's raged between Washington and Havana since the early 1960s.
In PPD-43, the White House has omitted important facts about the
intelligence relationship between the United States and Cuba—namely how
hostile it has been for more than 50 years.
For Havana, America possesses the only two existential threats to their
Communist system: the U.S. military, which outclasses Cuba's armed
forces a hundredfold, and the Cuban exile community, which Havana has
long considered a regime-change cadre in waiting. Cuba therefore has
spied intensely on America practically from the moment Fidel Castro took
power in 1959.
It needs to be said that Cuban espionage against the United States has
been impressive. Well trained by the Russians in spycraft, Havana's
intelligence services have consistently beaten Americans in the SpyWar,
displaying a discipline and seriousness that the regime lacks in other
Although it's practically unknown to the American public, Cuba has
consistently ranked among the Big Four counterintelligence threats to
our government (the others are Russia, China and Israel, in case you
wondered). Havana punches well above its weight in espionage and poses a
real threat to our national security—not least because the secrets it
steals from us with depressing ease don't always stay in Havana.
Perennially short of cash and lacking much of a legitimate export
economy, the Castro regime has a well-developed habit of selling
purloined American information to third countries such as Russia, China
Just how badly we've been beaten by Cuban spies is something Americans
should know. Our spy operations inside Cuba have been a bust from Day
One. It was bad news for our Intelligence Community in 1987 when the
highest-ranking Cuban intelligence defector to ever come to our side
revealed that every single agent run by the Central Intelligence Agency
since Castro came to power was actually fake. Some four dozen sources in
all, they had all been detected by Cuban counterintelligence and turned
into double agents for Havana.
This spy debacle, which revealed that the CIA had been decisively
outfoxed by Havana, made too little impression on Congress or the
public. Needed Intelligence Community reforms did not follow. Neither is
there any indication that things have gotten much better for the CIA in
the SpyWar against Cuba since 1987.
Even worse is the fact that Cuban intelligence has consistently managed
to beat our counterspies inside the United States, too. Lacking much of
a diplomatic presence in this country, Cuba for decades has nevertheless
done an impressive job of recruiting and running agents on American
soil, right under the noses of the Federal Bureau of Investigation.
Havana's secret tentacles extend deep into the émigré community and its
Miami base. There's really nothing happing in the Cuban-American world
that the Castro regime isn't aware of, and Havana has never lacked for
volunteers eager to spy on fellow Cubans. The only limit to Cuban
intelligence penetration of the émigré community, explained a top Cuban
intelligence defector to me, is the limited number of case officers that
Havana can infiltrate into the United States. There were always more
willing volunteers than Cuba could handle.
Indeed, Havana's penetration of émigré ranks is so deep and pervasive
that it can sometimes be difficult to determine what's really going on.
Cuban agent provocateurs are plentiful in Miami, and it can be safely
assumed that a significant percentage of the craziest-sounding
exiles—the ones agitating for violence and extremism—are really working
for Havana to discredit the Cuban-American community.
The so-called Wasp Network, consisting of five Cuban intelligence
officers and their many agents, which the FBI rolled up in 1998,
stretched deep into the Cuban émigré community in Florida. The Cubans
had even orchestrated the deaths of four anti-Castro activists in a
notorious 1996 incident. However, the Wasp Network had also penetrated
U.S. military installations in Florida, including U.S. Southern Command
in Miami, which is the Pentagon's headquarters for most of its Latin
Havana has consistently been able to recruit agents inside the Pentagon
and our Intelligence Community. The remarkable case of Ana Belén Montes,
a Defense Intelligence Agency senior analyst who spied for Cuba her
entire Pentagon career, caused less public waves than it merited, in
part because she was arrested just 10 days after the 9/11 attacks, when
media attention was elsewhere.
However, Montes did enormous damage to the Defense Department and our
spy agencies, since she was actively stealing secrets to pass to the
Cubans for more than 15 years. She was recruited by Castro's spy
services when she was a graduate student in Washington, and underwent
espionage training in Cuba before she joined DIA. In fact, her Cuban
handlers told her to get a job inside American intelligence, and Montes
She was unmasked thanks to diligent counterintelligence analysis by
several of our spy agencies, over years, and we learned from the Montes
case that she was only one of several Cuban moles lurking inside the
Beltway. One of those spies was caught in 2009. That was Kendall Myers,
a retired State Department analyst, who spied for Havana for three
decades, with his wife's assistance. His motivation, like Montes, was
ideological, not financial: Myers had a serious man-crush on Fidel Castro.
Other Cuban moles remain undetected. One may have been Alberto Coll, who
left the Naval War College in 2005, where he was a dean, under a cloud.
Coll, a former Pentagon senior official, was caught lying on official
forms. A Cuban émigré who came to the United States as a child, Coll had
taken trips to Cuba that he failed to tell security personnel about,
while he had friendships with Cuban spies he likewise did not disclose,
as he was required to. Coll was never charged with espionage, but many
Washington counterspies think his ties to Havana went deeper than has
ever been publicly revealed.
American counterintelligence hands who know the Cubans best have no
doubt that some of those moles remain active in and around Washington.
What's worse is that President Obama has now opened the door to
increased Cuban espionage against our country. Soon Cuba will have
brand-new diplomatic missions all over the United States and, per
standard practice, they will all contain a hefty number of spies posing
Given how successful Havana has been at conducting espionage against us,
on our own soil, without such large embassies and consulates, there's
every reason to expect Cuban spying to get more aggressive—and
effective—in the near future. President Obama has unilaterally declared
a truce in our half-century SpyWar with Cuba, but there's no indication
Havana has done the same.
John Schindler is a security expert and former National Security Agency
analyst and counterintelligence officer. A specialist in espionage and
terrorism, he's also been a Navy officer and a War College professor.
He's published four books and is on Twitter at @20committee.
Source: Obama Just Opened the Door for Castro's Spies | Observer -