‘A Very Deadly Woman': Ana Montes, Cuban's Top Spy in the US, to Leave Prison

A woman who infiltrated the U.S. intelligence community and spent years spying for Cuba's Castro regime is set to be released from prison this month.

The saga of Ana Belén Montes reads like something out of a spy novel: encrypted messages, clandestine meetings with handlers, secret disguises.

FBI officials call Montes' story a "classic tale of recruitment." After graduating from the University of Virginia and getting a master's from Johns Hopkins University, Montes was working a clerical job at the Department of Justice in 1984 when her views critical of the U.S. government's policies toward Central America caught the attention of the Cubans, who thought she'd be sympathetic to their cause.

After meeting with them, she agreed to help Cuba, and was able to get a job at the Defense Intelligence Agency, a key producer of intelligence for the Pentagon, in 1985.

"Her reason for spying wasn’t necessarily pro-Cuba, I wouldn’t describe her as socialist or a communist or a Marxist, I think she’s more idealistic and anti-American," said former FBI agent Peter Lapp, the Bureau's lead investigator on the Montes case. "From the day she walked in to DIA, she was fully recruited, she only went to DIA for the purpose of spying for the Cuban intelligence service."

Montes became the DIA’s top Cuban analyst and was known throughout the U.S. intelligence community for her expertise. The whole time, however, she was leaking classified U.S. military information and deliberately distorting the government’s views on Cuba.

FBI

To escape detection, Montes never removed any documents from work, electronically or in hard copy. Instead, she kept the details in her head and went home and typed them up on her laptop, the FBI said. Then, she transferred the information onto encrypted disks. After receiving instructions from the Cubans in code via short-wave radio, she'd meet with her handler and turn over the disks.

Scott Carmichael was the first DIA investigator who suspected Montes might be a traitor. In a 2007 interview, he said Montes was the ideal spy for 16 years, rising through the ranks at the DIA as a model employee.

"She was truly a professional spy, she was serious about the business," Carmichael said.

Former DIA investigator Chris Simmons said Montes was prolific and effective at giving the Cubans damaging intelligence, and they're suspected of selling that info to other enemies of the U.S.

"A lot of spies historically have given up information, but she repeatedly tried to get Americans killed in combat," Simmons said. "A very deadly woman, a very dangerous woman."

Investigators believe Montes provided the info which led to an American green beret being killed along with soldiers he was training in El Salvador. Prosecutors said she was involved in the infamous shootdown of the unarmed Brothers to the Rescue planes in 1996, when Cuban fighter pilots killed four Cuban Americans over international waters.

"That was her team, she was working with the Cuban government who murdered American citizens in cold blood," Lapp said. "So she didn’t pull the trigger but she was complicit after the fact."

Lapp said two Cuban defectors provided crucial tips which led the FBI to Montes. Using a FISA warrant, Lapp searched her Washington apartment several times, and found a shortwave radio which she used to receive coded messages from Cuba and a laptop which contained messages to and from her Cuban handlers,

He also found details about a top secret defense program, and the true identity of a U.S. spy in Cuba who Montes outed. Prosecutors said she ultimately revealed four American spies in Cuba.

Two of Montes' siblings actually work for the FBI, including a sister who's in the unit that looks for Cuban spies.

"I believe she does have blood on her hands," Lapp said. "Ana really betrayed not just our country and the government but the Montes family."

"The fact that she could fool her own family, two of whom work for the Bureau, shows the type of chameleon that she is, and we know she feels absolutely no remorse," Simmons said.

Authorities said Montes was willing to reveal American war plans in Afghanistan just before her arrest, but her ruse all came to an end when she was arrested by the FBI on Sept. 21, 2001, just 10 days after the 9/11 attacks.

Montes pled guilty in 2002 and has spent the past 22 years at a maximum security prison in Texas. Now 65, she's set to be released on Sunday, Federal Bureau of Prisons records show.

"I will say I think she’s pretty fortunate to be getting out of jail, there’s not a lot of spies of this caliber who walk out of prison and quite frankly, she could’ve spent the rest of her life in prison, frankly I would’ve preferred that," Lapp said.