1. Aldrich Ames – The Most Brazen Spy
Ames is a former CIA officer turned KGB mole. He was the son of a CIA officer and interned at the Agency when he was a sophomore in high school. He eventually became a full-time employee.
His career was not stellar. At his first overseas position in Mexico, he embarrassed himself numerous times due to his severe alcoholism. He also failed polygraphs and divorced his wife, then began to date a Columbian woman without informing his employer that he was seeing a foreign national, as required.
After Ames’ divorce, he had to pay alimony to his ex-wife, plus his new love interest had some fancy tastes. In 1985, he walked into the Russian embassy and volunteered to give them a few names of CIA sources for $50,000.
During his entire espionage career, Ames eventually took over $2 million from the Russians, and sold out virtually every American asset. The scandal was humiliating for the CIA, who had to admit that Ames routinely failed polygraphs, and nobody had bothered to question how a man with a $70,000 yearly salary could afford a new Jaguar and pay $560,000 in cash for a new house. He was convicted in 1994. He is serving a life sentence without the possibility of parole.
2. Robert Hanssen – The Most Perplexing Spy
Robert Hanssen is a former Federal Bureau of Investigation agent who spied Russian intelligence services against the United States for 22 years from 1979 to 2001, eventually taking $1.4 million in cash and diamonds for his deeds. His motives are unclear, even now, probably even to himself. He didn’t seem to need the money; unlike Ames he wasn’t flashy. In fact, he was deeply religious and lived modestly. The root of his acts is probably insecurity; he felt he was smarter than everyone else and wanted to prove it.
On July 6, 2001, he pleaded guilty to 15 counts of espionage and was sentenced to 15 life terms without the possibility of parole. His activities have been described by the Department of Justice’s Commission for the Review of FBI Security Programs as “possibly the worst intelligence disaster in U.S. history.” The extent of his damage to the US with his spying is still classified.
3. Harold James Nicholson. The Most Audacious Spy.
Harold James Nicholson is the highest-ranking CIA officer to ever be convicted of espionage. He began to spy for the Russian Foreign Intelligence Service (SVR) in the wake of Aldrich’s arrest in February 1994. His motives were money, though he cloaked it in concern for his children. He was sentenced to nearly 24 years in prison.
When Russia recruited agents inside the US, they set aside money for them in case they defect to Russia (this is sometimes referred to as a pension.) Since Nicholson knew Russia still had money for him, he decided to access with a diabolical plan. From behind bars, he recruited his youngest son to continue spying for Russia. Nathaniel Nicholson collected more than $48,000 from the Russians in Mexico, Peru and Cypus, payment for his father’s past spy work. Nathaniel was given probation after helping prosecutors build a case against his father while Harold James Nicholson received eight more years for the unprecedented act of spying for Russia for a second time. Nicholson is incarcerated in Supermax prison in Colorado, and is scheduled for release in 2024.
4. Ronald Pelton – The Most Desperate Spy
Ronald William Pelton is a former NSA intelligence analyst who sold secrets to Russia after hitting financial difficulties. In 1979, Pelton declared personal bankruptcy and resigned from his $24,500-a-year job ($80,800 today) with the NSA A Group. On January 14, 1980, Palton contacted the Soviet embassy in Washington DC and arranged a meeting. During the meeting, he disclosed details of Operation Ivy Bells, an NSA and Navy program to secretly wiretap undersea cables to monitor Soviet military communications and track Soviet submarines. He had no documents to offer, but he had his memory – and he spilled everything he knew until 1984, collecting about $37,000 from the Soviets.
In 1985, his handler VitalyYurchenko defected to the US. When he was debriefed by the FBI and CIA, he mentioned he met with a former NSA analyst in 1980 and said he had red hair. The FBI quickly realized Pelton was the one. He was convicted in 1986 and sentenced to three life sentences. He was released on November 24, 2015.
5. Jonathan Pollard–The Guy Most Likely To Spy
Pollard was a bit of a fabulist, a bit of a troubled soul, and a bit of an asshole. He had a weird fascination with spywork from a young age, and when he failed to be hired on the CIA due to admitting to prolific pot smoking, he tried the US Navy. Two months after he was hired, the director of his group asked that he be fired due to lying about his father’s CIA service (which was non-existent) and offered to start a back channel operation with the South African intelligence service. But he was kicked upstairs. He continued to befuddle and annoy his bosses, and attempts to dismiss him were repeatedly foiled.
Pollard met a colonel in the Israeli Air Force and volunteered to work as a spy. Within a few days, he passed the first bundle of information and was paid $10,000 and given an expensive diamond and sapphire ring. He also continued to try to spy for South Africa and even Pakistan and China. He was finally investigated in 1985, convicted, and sentenced to a life term.
On November 20, 2015, after 30 years behind bars, Pollard was released from prison.
6. Earl Edwin Pitts
Pitts’ spying began when he was working on at FBI’s foreign counter-intelligence investigations in the New York Office from January 1987 to August 1989. During this time, he accepted over $224,000 for turning over classified materials including a secret computerized FBI list of all Soviet officials in the US with their known or suspected posts in Soviet Spy agencies.
Pitts was discovered after a Soviet defector identified him to the FBI and assisted the FBI in their sting operation. Years after he had stopped spying – during which the FBI was investigating him – his KGB contact approached him at his home and asked to speak with him. Pitts demurred and told him that he had told him everything he knew. But he made many incriminating statements about his prior activity. When asked why he had spied for the Soviets, he said he wanted to “pay them back”. During his debriefing by the FBI, he was asked if he was working with any other spies. He said no, but he was suspicious of Robert Hanssen. Hanssen continued to spy until 2001.
In June 1997 Pitts was convicted of espionage and sentenced to 27 years in prison.