In the post–Cold War era, the longest and most damaging penetration of the U.S. military was perpetrated by Ana Belen Montes, a Defense Intelligence Agency (DIA) analyst arrested in September 2001. Born in the United States of Puerto Rican parentage, she graduated from Johns Hopkins University and joined the Department of Justice before she transferred to the DIA in 1985 as a Spanish-speaking specialist on Cuba. She made two visits to Havana for the DIA in 1993 and 1998, and at the time of arrest, in her midforties and unmarried, she was a senior analyst who had briefed Congress and the Central Intelligence Agency, was cleared for Special Access Programs and Intelink, the U.S. intelligence community’s internal data exchange, and had passed her polygraph tests. Her brother was a Federal Bureau of Investigation special agent in Florida, and her sister was an FBI translator.
Under interrogation, Montes acknowledged that she had been recruited by the Cuban Dirección General de Inteligencia (DGI) before she had even joined the DIAand had been vectored into her post. She admitted to having betrayed U.S. war contingency plans and telling the Cubans the names of four CIA officers working under diplomatic cover at the American Interests Section of the Swiss embassy in Havana. Montes seems to have declined the opportunity of a promotion to retain her access, apparently because she wanted to continue to influence U.S. policy on Cuba, a commitment for which she showed absolutely no remorse when she cooperated with the damage assessment conducted at her prison in Fort Worth. Indeed, she asserted her hope that her conviction would help American policy makers reconsider the continuing U.S. economic blockade.
From the DIA’s standpoint, the Montes penetration represented a 16-year disaster, longer than the betrayals perpetrated by Aldrich Ames and Robert Hanssen, and had been sustained by more than 300 meetings with Cubans operating not from the Cuban Interests Section in Washington, D.C., but as illegals. The FBI’s decision to arrest Montes was prompted by the terrorist attack of 11 September 2001 and the fear that her information might leak to another adversary and assist in a further atrocity or compromise military retaliation in Afghanistan.