CHAPTER 8
CUBAN OPS
I
had always hoped to visit Old Havana before Fidel Castro died. A
leisurely sojourn to this Spanish Colonial marvel, frozen in time for
the past sixty years, was high up on my bucket list. Savoring ropa vieja
while sipping a mojito and grooving to the mesmerizing prerevolutionary
boleros of the group Buena Vista Social Club in a dimly lit Cuban joint
in Miami, while really nice, cannot possibly equal that same sublime
experience in Havana.
I came close a couple of times. The CIA tasked me to TDY to Havana
over Christmas 1995 to probe, survey, and generally mess with the DGI,
the exceptionally competent and aggressive KGB-created Cuban security
service. Since I’d be working there under the protective umbrella of Cold
War rules, the most the DGI could do was rough me up a bit before tossing
me off the island. In this sense, getting caught while screwing with the DGI
as an American spy is vastly preferable to getting caught while screwing
with ISIS as an American spy. Or as an American anything for that matter.
There were definitely tangible benefits to operating under the unwritten
but generally respected Cold War rules.
The CIA selected me for the Havana mission because of my Latin
America tour, but primarily because of my recent denied area experi-
ence in Yugoslavia operating against real Communist thug surveillance.
The DGI, like the KGB and others of their ilk, understandably fear agents
and other representatives of democratic societies, and they do their best
to protect their illegitimate, unelected masters from the threat posed by
freedom by keeping us under their dirty, heavy thumbs.
But I digress.
I’d also successfully completed the CIA’s intensive denied area surveil-
lance training course. If I were under surveillance in Cuba—and I would99