‘A very deadly woman:’ Ana Montes released from jail

Ana Montes was billed as a "very deadly woman" who had "blood on her hands," per the investigators who put her in jail. Now, she's out.
Logan Nye Avatar

Ana Belen Montes spent 17 years spying for Cuba. She memorized massive amounts of data in the Defense Intelligence Agency and then transcribed it in notes to the Castros. The Cubans likely passed the bulk of that information on to Russia, Iran, and other buyers.

And she didn’t do it for money. She wasn’t blackmailed. She wasn’t forced or coerced. Cuba got the information nearly for free.

But they did try to satisfy one big ask by Ms. Montes: When she got lonely, she requested a lover. But, to be blunt, it turned out that Cuban intelligence sucks at matchmaking.

Ana Montes serves Cuba, asks for one thing in return

Ana Montes Montes received a certificate of distinction from George Tenet, CIA Director, in 1997. Wikimedia Commons.

Ana descended from a patriotic family, and she had two siblings and a sister-in-law in the FBI. But she found herself increasingly drawn to socialist causes and against U.S. imperialism. So, in 1984, Cuba asked for her services and she agreed. She got a job at the Defense Intelligence Agency, which works for the Department of Defense and concentrates on military matters.

During the day, Ana sat at her desk and focused her impressive mental acumen on Cuban affairs. And she quickly rose in the ranks and earned medals for her service. But at night, she used her impressive mental acumen to transcribe documents she had seen that day.

The U.S. gave her medals for daytime work, and Cuba gave her medals for moonlighting.

A cheat code for Ana Montes
A “cheat sheet” provided by Cuban intelligence that Ana Montes used to help her encrypt and decrypt messages to and from her handlers. Wikimedia Commons.

But Ana Montes found her work lonely. After all, she had to be extremely careful not to tip her hand to anyone. She had no close friends and had to distance herself from her FBI-filled family. And she couldn’t date conventionally since her apartment had spy gear stashed in it and her schedule of listening to radio broadcasts and typing up documents would beg a lot of questions.

And so she did the logical thing: She asked Cuba for a boy toy. For some man meat. For a Lothario, a masher, a rake, a lounge lizard.

The man for Ana Belen Montes

Peter J. Lapp, one of the FBI agents who caught Ana, shared details of her request—and a lot more about Ana’s life, crimes, and eventual fall—in his new book, Queen of Cuba: An FBI Agent’s Insider Account of the Spy Who Evaded Detection for 17 Years.

Her requests were fairly doable. In 1998, she asked for “…someone Latin, smart, good-looking, and athletic who didn’t smoke—from a country known for its cigars and 60 percent smoking rate,” according to Lapp.

Sure, it might take some work to find a nonsmoker. Or it could take work for a smoking Cuban intelligence officer to quit smoking, or at least cover or hide his smoking. But other than that, finding a fit, Cuban man in a country with food and gas rationing seemed achievable.

Ana gets her mate

The Cubans agreed to find her a man. And they set up a rendezvous for the arranged, loving couple on a Caribbean island.

But Ana later complained about her match. As Lapp wrote in his book, “Ana realized she would have to find someone for herself. Her new Cuban friend was overweight. He smoked. He was not athletic.”

So, you know, still Latin. And no clear indication he wasn’t smart and otherwise handsome. So 60% success, three out of five traits, for the Cuban handlers and matchmakers.

Seems like Ana was being a bit choosy for an isolated spy. But she would get even more isolated a few years later when she was arrested and sent to prison.

Ana gets caught

Just three years later, even as Ana was trying to wrap up her spying career, she got caught. The U.S. had known they had a mole for Cuba in the mix somewhere. It took years for the FBI to realize that Ana was their woman (spies are rarely single women with no lavish spending), but they happened to close in on Ana in 2001.

The DIA was convinced Ana was the spy, but the FBI asked for them to isolate her without tipping their hands. They wanted to get enough evidence for a conviction, and that investigation would take time.

When the attacks of 9/11 raised the stakes for the DIA, though, the agency told the FBI to arrest Ana or they would fire her to protect information around the anticipated invasion.

Lapp and the rest of the agents assigned to finding and stopping Ana went to the courts with all that they had, and the courts agreed to an arrest warrant. The investigators in charge of the case called Montes “a very deadly woman,” and were convinced she had “blood on her hands.”

Ana was arrested just 10 days after the attacks. And, according to Lapp, she did plan to send information about the invasion to Cuba. She believed that America had a right to respond to the attacks and to invade, but she wanted Cuba to have the intelligence about how to defend themselves if the U.S. ever invaded them.

And if Cuba sold the plans to the Taliban or others? Well, that was a risk that American troops signed up for.

Ana was sentenced to prison and spent over 20 years in confinement. But on January 6, 2023, she got out and has said she plans to move to Puerto Rico. Maybe she’ll find a fit, Latin, non-smoker there. And perhaps a bit of patriotism or shame.


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Logan was an Army journalist and paratrooper in the 82nd Airborne Division. Now, he’s a freelance writer and live-streamer. In addition to covering military and conflict news at WeAreTheMighty, he has an upcoming military literacy channel on Twitch.tv/logannyewrites.