A Career Spanning Three Worlds

Enrique “Ricky” Prado built one of the most remarkable resumes in CIA history. His official career included operations during the Central American conflicts, intelligence work in Korea, espionage programs targeting China, and a senior position under counterterrorism chief Cofer Black. After leaving the agency, he joined the private military firm Blackwater.

But according to an extensive investigation by journalist Evan Wright — author of the Iraq War chronicle Generation Kill — Prado’s career had a far darker dimension. Wright’s reporting, published as How to Get Away With Murder in America, compiled years of state and federal police investigations suggesting Prado began his professional life as an alleged hitman for a Miami organized crime figure, and that his connections to the criminal underworld persisted even after he entered the intelligence community.

Origins in Miami’s Criminal Underground

According to Wright’s investigation, Prado’s alleged criminal career began through his relationship with Alberto San Pedro, a Cuban exile who became one of Miami’s most prominent cocaine traffickers. The two reportedly met as high school students in Miami after their families fled Cuba following the revolution.

San Pedro built a criminal empire that imported tens of millions of dollars worth of cocaine annually into the United States, according to the investigation. His social network reportedly extended into Miami’s political and media establishment, including connections to a gubernatorial aide, multiple judges, lobbyists, and a state prosecutor.

Prado joined the Air Force but never deployed to Vietnam. After returning to Miami, he worked as a firefighter while allegedly carrying out contract killings for San Pedro’s organization. Investigators from the Miami-Dade Police Department’s organized crime unit suspected him of involvement in at least seven murders and one attempted murder.

Entry Into the CIA Despite Red Flags

Prado initially attempted to join the CIA but reportedly withdrew before completing the background check, allegedly due to concerns about scrutiny of his family connections. He was later admitted to the agency during the Reagan administration’s covert operations against leftist movements in Central America, where he reportedly trained Contra fighters.

What made the situation more alarming, according to the investigation, was that the alleged killings in Miami continued after Prado joined the CIA. One case involved a cocaine distributor in Colorado who was killed by a car bomb — reportedly because of fears he would cooperate with police.

Wright characterized the situation as a new form of institutional compromise. Rather than a foreign agent penetrating the CIA, the agency had allegedly allowed someone working on behalf of domestic criminal interests to rise through its ranks.

Rise to the Top of Counterterrorism

By 1996, Prado had become a senior manager inside the CIA’s Bin Laden Issue Station, years before the Al-Qaeda leader became a household name. Following the 1998 embassy bombings in Kenya and Tanzania, Prado was elevated to chief of operations at the CIA’s Counterterrorist Center under Cofer Black.

In that role, Prado oversaw field offices conducting surveillance, renditions, and other operations. He was also reportedly placed in charge of a targeted assassination program that was ultimately never activated — the CIA shifted its focus to drone strikes instead.

The Privatization of Assassination

According to Wright’s reporting, the CIA eventually transferred its dormant assassination capability to Blackwater. Prado allegedly negotiated the deal, which Wright described as the first known instance of the United States government outsourcing a covert killing operation to a private company.

Whether that unit subsequently became operational remained a matter of dispute, though two Blackwater contractors told Wright it began active operations in 2008.

Separate reporting revealed that after leaving the CIA, Prado constructed a network of foreign shell companies to conceal Blackwater operations beginning in 2004. A 2007 communication to the Drug Enforcement Administration pitched Blackwater’s capabilities for surveillance, intelligence gathering, and disruption operations — carried out by foreign nationals to provide built-in deniability.

Unanswered Questions

The full extent of Prado’s alleged criminal ties remained unclear. One theory suggested he sought legitimate employment in the military, firefighting, and intelligence work as an escape from his obligations to San Pedro’s organization, but found himself unable to sever those connections.

The broader question concerned the CIA itself. The agency had a documented history of associations with morally compromised individuals in pursuit of intelligence objectives. Yet the Prado case, if the allegations were accurate, represented something different — not a calculated relationship with a foreign asset, but a potential failure to detect that one of its own senior officers was allegedly operating on behalf of domestic criminal interests throughout his career.

Multiple police investigations into the alleged crimes were either sidelined by higher-ranking officials, ended without resolution, or resulted in minimal sentences — raising questions about whether institutional protection played a role in shielding both San Pedro’s network and Prado himself from accountability.