The spycatcher who guessed a retired NSA clerk’s secret password

Robert Lipka wanted proof that the man claiming to represent Moscow really knew his past. In a 2016 Smithsonian interview, retired FBI agent Dimitry Droujinsky described meeting Lipka undercover in Pennsylvania in 1993. Lipka demanded a code word and traced its beginning in dust on his dashboard. Droujinsky did not have it. Remembering Lipka’s comment about playing chess with an old handler, the agent tried a guess at their next meeting: rook. According to Droujinsky’s recollection, it was right.

Lipka had gained access to intelligence through a routine processing job. An Army historian’s account describes his assignment to the NSA at nineteen in 1964, working in a central communications room. His duties involved collecting classified reports from teleprinters, distributing them around the agency or destroying them. In September 1965, he approached the Soviet Embassy offering material for cash. The position placed documents within reach even though he was a junior enlisted soldier, rather than a senior analyst directing American intelligence.

The inquiry revived after information in the Mitrokhin archive and a report from Lipka’s former wife drew FBI attention in the early 1990s. The Army history says Droujinsky posed as a Russian intelligence officer seeking renewed contact. Lipka complained about unpaid compensation from his earlier spying. Investigators paid him $10,000 over several months while building evidence. He admitted supplying the KGB in the 1960s and offered documents he still possessed from the NSA. The bureau stopped contact in December 1993 but continued assembling its case.

Agents arrested Lipka on February 23, 1996, long after the work that had first put him in Moscow’s service. He pleaded guilty to espionage and received an eighteen-year sentence.

He was released in December 2006 after serving roughly half that term. Smithsonian’s account reports his death in 2013. The password episode remains an attributed recollection from the undercover officer, but the plea and sentence establish the result: a short period of access in the 1960s had produced a prosecution three decades later.