Prosecutors moved Thursday to strip the U.S. citizenship from Manuel Rocha, the former American ambassador who in 2024 admitted he spent nearly half a century working as a spy for Cuba while serving in senior State Department positions. In a civil denaturalization complaint filed in Miami, the U.S. Attorney’s Office alleged the Colombian-born Rocha, 75, concealed his long relationship with Cuban intelligence when he swore allegiance to the United States during naturalization in 1978.

Rocha was sentenced to 15 years in federal prison after pleading guilty to 15 counts of acting as an illegal foreign agent. His arrest in late 2023 and subsequent plea closed the fifty-year operational arc of one of the most damaging humint penetrations in U.S. diplomatic history. An undercover FBI agent recorded Rocha praising Fidel Castro as “El Comandante” and calling his decades of espionage “more than a grand slam” against the U.S. “enemy.”

The criminal case left unresolved whether Rocha used his diplomatic access—postings included ambassador to Bolivia, toplevel assignments in Argentina, Mexico, the White House, and the U.S. interests section in Havana—to compromise U.S. personnel, operations, or secrets. As part of his plea, Rocha acknowledged that he first connected with Cuban intelligence agents in 1973, five years before he applied for citizenship, while at a student program in Chile at the twilight of Salvador Allende’s presidency. At Havana’s direction, he subsequently enrolled at Harvard and Georgetown universities on his way to securing a career inside the State Department.

Prosecutors now argue Rocha lied repeatedly under oath during his naturalization interview. The complaint alleges that when applying to become a U.S. citizen he stated he “believed in the U.S. Constitution” and denied any affiliation with Cuba’s Communist Party—an assertion contradicted by his own later sworn admissions. Federal law allows denaturalization only when an individual procured citizenship illegally or by willful misrepresentation of a material fact, a standard U.S. Attorney Jason A. Reding Quiñones said his office intends to meet. “This civil denaturalization case is about finishing the job,” Quiñones said.

The legal effort to revoke Rocha’s citizenship is the latest step in a quiet expansion of denaturalization actions. The Justice Department issued internal guidance last year asking prosecutors to prioritize cases against individuals who “pose a potential danger to national security,” including those involving terrorism and espionage. In the same week the Rocha complaint was filed, the administration moved to revoke citizenship from 11 other convicted individuals, among them people convicted of providing material support to terrorists and child sexual abuse offenses. Between 1990 and 2017, denaturalization was pursued only about a dozen times a year.

The effort to roll up Rocha’s legacy has been shadowed by the Central Intelligence Agency’s failure to identify him as Cuba’s “super mole” within the U.S. government despite warnings dating to the 1980s. An Associated Press investigation found that a CIA operative first flagged Rocha as a probable double agent nearly twenty years before his arrest, and that intelligence collected as early as 1987 suggested Fidel Castro had a highly-placed source burrowed inside the U.S. government. Some officials came to suspect that the mole might be Rocha. After his arrest, he spent months being debriefed by federal officials, though it remains unclear what additional damage assessments were completed.

The denaturalization complaint is not a criminal charge but a civil action that, if successful, would strip Rocha of the rights and privileges of citizenship while he remains incarcerated. Officials did not say whether the effort could eventually lead to deportation after he completes his prison sentence.