Hear more about Jim Nicholson on True Spies podcast: The Spy’s Son Parts 1 & 2

Harry James Nicholson was convicted of spying for Russia - twice - and released from prison in November 2023. So what does a master manipulator do for an encore? 
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CIA officer Jim Nicholson saw himself as a superhero during his time in South Asia. His radio call sign was ‘Batman’ and the supremely confident operator appeared to be on the fast track in the '90s.

The CIA and Russia had struck an intelligence-sharing deal to tackle Islamic terrorism after the collapse of the Soviet Union in 1991, so it was natural for Jim to meet Moscow’s SVR officers. At one point, though, probably around 1994, Jim Nicholson crossed the Rubicon, entered the Russian Embassy, and offered intelligence for cash. 

The high-ranking CIA officer sold national defense intelligence, revealed the identities of all CIA officers stationed in Russia, and sold files on CIA trainees including his own students. He was caught in ‘96 - handcuffed and splayed across a car at Dulles airport - but even prison couldn’t stop Jim Nicholson. While serving time in Oregon, Nicholson was still running a spy on Moscow’s behalf - his own son.
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The Spy Hunt

Things started to unravel In 1995 when a Russian asset tipped off the FBI about a mole in the Agency. It was a couple of years after the arrest of CIA traitor Aldrich Ames and the top brass were still jumpy. The Russian asset didn’t have a name but sketched out a profile, so when Jim Nicholson failed a routine polygraph, he was put under surveillance. Nicholson’s meeting with Russians in Singapore confirmed the FBI’s suspicions. But if they wanted to make an arrest, it needed to be on US soil. 

It was time to set an elaborate trap. The joint FBI-CIA team tapped John Maguire, an ex-Baltimore cop turned CIA counterterrorism expert, to headline a unique spy-vs-spy operation at the Agency's sprawling compound in Langley, Virginia. “Welcome aboard,” FBI agent Ed Curran said when Maguire passed a polygraph test. “We have another Ames.”
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Spy vs Spy

Their target, Jim Nicholson, was now back in the US, working as an instructor at the Farm, the CIA’s legendary training facility. The role gave Jim access to personnel reports and compromising intel about the next generation of CIA officers - excellent fodder for the Kremlin - so the FBI-CIA team moved Jim to a different supervisory role. John Maguire was embedded as his deputy. The ex-Baltimore cop was now Jim Nicholson’s shadow.

The stakes were high. John’s boss made that abundantly clear, Maguire told the True Spies podcast: “If you successfully do this, you'll have accomplished something that really matters and you'll get your pick of assignments,” John recalled his supervisor saying, and “If you f*** this up, you're finished.”

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Bringing down a Russian spy

Luckily, Jim Nicholson was always working an angle. He trusted his new deputy and became more relaxed - sloppy, even. One day, he took John to a post office where there was something fishy about the stamps Jim was so keen to collect. “That's a clear indicator. He's going to mail something and the stamp means something,” John said. He passed his suspicions to the FBI and things moved quickly. “I was stunned by what they were able to pull together so fast.”

Later that night, Jim Nicholson’s Chevy crawled out into the darkness - just him, a postcard bearing a unique stamp, and a fleet of FBI surveillance vehicles trailing discreetly behind. The Bureau now had access to Nicholson’s home, laptop, and document scanner. A pinhole camera had already been mounted above Nicholson’s desk at CIA HQ. Through it, the FBI secretly watched Jim’s every move.

Jim, a gadget-lover, had asked the CIA tech team to borrow a hi-res camera hidden in a briefcase. It was the same camera Jim used to snap document after CIA document while the FBI watched through their pin-hole camera planted in Jim's office. The US attorney was satisfied. On November 16, 1996, Jim Nicholson arrived at Dulles International Airport with $50,000 in classified CIA documents stored on film in his camera bag. FBI agents disguised as passengers kept eyes on the mole. As he strode out onto the tarmac, Jim was handcuffed.

John Maguire watched Nicholson’s life evaporate in front of his eyes. The FBI-CIA operation, some 10 months in the making, was finally at a close - or so they thought. 
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Running spies in prison

Jim was sentenced to more than 23 years and served his time in Oregon. The location allowed Jim to stay close to his family - too close. Nathan Nicholson was 12 years old when his father was jailed, and over the next decade of prison visits, Jim would groom his son to spy for Russia. Nathan now thought of himself as Batman’s sidekick, Robin.

Jim “was a master manipulator. But at the end of the day, it really is about a son trying to find his place in the world with his own father,” Ethan Knight, Assistant US Attorney in Portland, Oregon, told True Spies. Knight handled the case.

In October 2006, with Jim still behind bars, Nathan entered the Russian consulate in San Francisco and offered the chief of security a letter. It introduced him as the son of Jim Nicholson, one of the highest-ranking CIA officers to ever sell secrets to the Kremlin. The Russians told Nathan to come back in two weeks. They wanted to check out his story. Jim Nicholson was not concerned. Spying is a complex game - and a long one.

On his second trip to San Francisco, Nathan left the Russian consulate with $5,000 in cash - a token of goodwill from Moscow - and a promise of future collaboration. Nathan was excited to share the news with his father but knew the prison phone was monitored. Addressing him in code, Nathan told Jim he'd cleared an impressive insurance sale in San Francisco and was planning a ‘business trip’ to Mexico City. 
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Selling Secrets to Moscow

Jim Nicholson may have been warming the bench in prison for a decade, but he still had intel to sell - his arrest in ‘96 held clues about how the FBI investigates traitors, their identities, and the names of those who may have spied on Jim at the CIA. Nathan delivered his father's intelligence to the Russian Embassy in Mexico City and left with $10,000 - another win - but the young courier was getting used to the routine and becoming a bit careless in communications with his father.

“There was one line in a call or a letter, and he slipped and said: ‘How's that… ‘thing’ going?’ And it was just enough of an opening, enough daylight,” Knight said. “That began to give way to ‘maybe something else was going on.’”

Analysts alerted the FBI. The Justice Department issued warrants for electronic and physical surveillance on both men. The FBI tapped Nathan's cell phone and computer. His car was tracked. During one foreign trip, Nathan passed through airport security and his bags were earmarked for a ‘random’ Customs inspection. The FBI found his journal, a goldmine of names, dates, and trips. None were coded.

When he flew to Cyprus, Nathan met his Russian handler at 7 pm on December 10 at TGI Fridays restaurant. The FBI was there to record the meeting. The 24-year-old left with $12,000 but the gig was up. Back home, the FBI came knocking on Nathan’s door 10 days before Christmas. After initially lying, Nathan decided to cooperate and confront some painful home truths.

“It was a gradual process, I think, for Nathan to realize what had really happened to him, that he had been manipulated,” said Knight. “And, at the end of the day, his dad had run him as a source.”

Uncomfortable truths

Ultimately, Nathan Nicholson received five years probation on the condition he testify against his father. Jim Nicholson got eight extra years at a maximum security prison in Colorado, one that has also housed El Chapo, Robert Hanssen, and the Boston Marathon bomber. In November 2023, Nicholson was finally released.

So what happens to a captured spy when he is finally set free? Nicholson earned about $300,000 selling US secrets but the FBI arrested him before Jim could pocket all of the money. He may still be hoping to collect his pension.

“I expect him to be gone in a flash,” John Maguire said. “If he wants to get away, he'll get out of the country. And he'll go somewhere and meet up with the Russians and get the money that they owe him.” 
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