As agents were closing in on Ana Montes, one reported the espionage investigation to Robert Hanssen
By Shane Harris, Washington Post
November 30, 2022 at 5:58 p.m. EST
In late 2000, the FBI was closing in on a suspected spy for Cuba working inside the Defense Intelligence Agency. Undercover operatives would soon begin trailing Ana Montes, the agency’s top military and political analyst on Cuba, by car and on foot. They filmed her making calls on pay phones, even though she carried a cellphone in her purse. They intercepted Montes’s mail and inspected the trash outside her apartment in Washington.
Montes had been spying nearly 17 years for Cuba, passing along so much classified information about DIA personnel, as well as on eavesdropping technology covertly installed on the island, that she essentially compromised every method the United States used to surveil the Castro regime, according to current and former U.S. intelligence officials. That makes Montes one of the most damaging spies of her time, they said.
Opening an investigation against a decorated intelligence officer, who colleagues heralded as the “Queen of Cuba,” was painstaking and high-stakes. And almost as soon it began, the FBI nearly shot itself in the foot.
The slip-up was inadvertent. Whenever the bureau began an intelligence investigation that might ruffle feathers in a foreign government or upset U.S. foreign policy, officials typically informed the State Department’s Office of Foreign Missions (OFM). It was a sleepy outfit, responsible for keeping tabs on travel by foreign diplomats and overseeing such things as plans to build new embassies or consulates in the United States. Hardly the setting for an espionage thriller.
So Terry Holstad, then the chief of the Cuba unit at FBI headquarters, never thought twice when he described the secretive Montes investigation to the bureau’s liaison to the OFM, a veteran agent and longtime colleague named Robert Hanssen.
Unbeknown to Holstad and the rest of the FBI, Hanssen had started spying for Russia more than 20 years earlier. He gave thousands of pages of classified documents to the KGB, divulging secrets about U.S. nuclear war planning and weapons technology. He compromised the identities of dozens of human sources, at least three of whom were executed, according to a review by the Justice Department’s inspector general, which called Hanssen “the most damaging spy in FBI history.”
Feature continues here: FBI Mistake