Ana Montes received a certificate of distinction from CIA Director George Tenet in 1997. Four years later, FBI agents arrested her at her Defense Intelligence Agency office. During those years, Montes was also working for Cuban intelligence.
The arrest announcement, dated September 21, 2001, says agents took Montes into custody that morning without incident at DIA headquarters at Bolling Air Force Base in Washington. She was 44. The complaint charged conspiracy to deliver US national defense information to Cuba under 18 USC 794(c). Investigators also obtained search warrants for her home, car, office and safe-deposit box.
Her espionage had lasted through most of her DIA career. The case connects a recruitment operation that began before she joined the agency with a method of passing secrets that relied heavily on memory, encrypted computer files and radio instructions.
Recruited before she entered DIA
The Justice Department's 2013 announcement of an unsealed indictment against Marta Rita Velazquez supplies a detailed account of the alleged recruitment network.
Prosecutors alleged that Velazquez befriended Montes while both studied at Johns Hopkins' School of Advanced International Studies in Washington. In December 1984, the indictment alleged, Velazquez introduced her in New York to a Cuban intelligence officer presenting himself as a Cuban Mission official.
The government further alleged that Velazquez accompanied Montes to Cuba for intelligence training in 1985 and helped her obtain a DIA job later that year. Those were allegations against Velazquez; the announcement did not establish her guilt. Montes's own conviction is a separate matter. The same release records that she worked at DIA from September 1985 until her arrest and pleaded guilty on March 19, 2002, to conspiracy to commit espionage for Cuba.
How secrets left the office
In a 2023 Washingtonian interview, author Jim Popkin described how Montes avoided carrying documents out of work in nearly all instances. She memorized information, typed it into an encrypted Toshiba laptop at home and periodically handed a disk to a Cuban handler at meetings in Washington restaurants.
Popkin's account also describes coded telephone calls from a payphone near the National Zoo and efforts to spot surveillance by doubling back through the zoo.
The warning that resurfaced
The FBI's case history traces an early warning to 1996, when a DIA colleague reported a suspicion that Montes might be under Cuban influence. A security official interviewed her, but she admitted nothing.
Four years later, that official learned the FBI was looking for an unidentified Cuban agent in Washington and contacted the bureau. Investigators used surveillance and covert searches to build their case. They initially wanted to identify her handler and waited for a meeting.
Popkin describes another part of the hunt: National Security Agency analysts obtained information that helped them decode Cuban shortwave transmissions referring to an unidentified 'Agent S.' They concluded the source was probably a significant US intelligence official. According to his account, the FBI initially thought it was looking for a man and made little headway for more than two years. An NSA analyst then took the information to DIA, where investigators identified Montes.
The September 11 attacks changed the timing. According to the FBI, Montes was approaching an assignment involving US war plans, and the agencies moved to arrest her before she received that access. Her arrest ten days after the attacks did not mean she was implicated in them.
The FBI says ideology motivated her: she opposed US foreign policy and accepted expense reimbursements rather than payment for secrets. It also records that she had passed a polygraph.
What she admitted, and what remains classified
Associated Press reporting records that Montes acknowledged exposing four undercover US agents to Cuba. Prosecutors said at the time that those four were not harmed. AP also reported that court records described disclosures about US surveillance of Cuban weapons, while other secrets were too sensitive to describe publicly.
In March 2003 congressional testimony, FBI Director Robert Mueller cited Montes's conviction while describing a broader counterintelligence reorganization. He said the bureau had established a Counterespionage Section, shifted 216 positions from criminal investigations to counterintelligence and placed full-time counterintelligence squads in 48 of its 56 field offices. The account placed foreign penetration of US intelligence among the bureau's stated threats. Mueller described these as changes to the wider program, discussing other espionage cases in the same testimony.
The government also examined how Montes had escaped detection. A June 16, 2005, Defense Department inspector general report reviewed deterrence, detection and investigation of her espionage. The National Security Archive's catalog identifies its source as a Defense Department Freedom of Information Act appeal release and places it in a sourcebook published in 2015.
Montes received a 25-year prison sentence in 2002. ABC News reported that prison officials confirmed her release on January 6, 2023, after a little more than 21 years in custody.
