THE SPY'S SON, PART 2, DARK INHERITANCE

True Spies: The Spy’s Son, Part 2, Dark Inheritance

Welcome to True Spies. Week by week, mission by mission, you’ll hear the true stories behind the world’s greatest espionage operations. You’ll meet the people who navigate this secret world. What do they know? What are their skills? And what would you do in their position? I’m Vanessa Kirby, and this is True Spies: The Spy’s Son, Part 2.

NARRATOR: It’s early morning in San Francisco, and a young man in a crumpled black suit is trudging resolutely uphill. He’s exhausted - courtesy of an eight-hour drive from Portland - and the streets are punishingly steep. But he’s been given a mission and the price of failure is steeper still. 

ETHAN KNIGHT: He'd gone to the consulate, the nearest one at that time by car from Portland, Oregon, and went in. 

NARRATOR: The Russian Consulate, to be exact. An imposing, dust-colored block, just a stone's throw from the Presidio National Park. The disheveled visitor’s name is Nathan Nicholson. It’s early October 2006, and he’s 22 years old. He enters the consulate and requests an audience with the Chief of Security. He gets it.

ETHAN KNIGHT: Announced who he was, offered a letter.

NARRATOR: In a soundproof room, deep inside the building, the security chief takes a quizzical glance at Nathan’s neatly folded letter. It reassures the Russian that the boy across the table is the son of the highest-ranking CIA officer to ever sell secrets to the Kremlin. Jim Nicholson. Let’s rewind. In the first episode of this True Spy story, we followed Jim’s spectacular fall from grace in 1996.

JOHN MAGUIRE: Nicholson was one of the highest-ranking people ever to become involved in something like this and was working in a sensitive global center related to terrorism. So there was a tremendous amount of risk of what was coming out and leaking out because of him. 

NARRATOR: Now, we’re returning to the story a decade later for the second act in a long career of treachery - Nicholson’s manipulation of his son, Nathan, in order to continue selling secrets from behind bars.

ETHAN KNIGHT: It's a fascinating story that gives us insight into the mind of a spy and a traitor at the outset. It was clear that this was someone who 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.

NARRATOR: Meet your guide to this extraordinary father-son relationship.

ETHAN KNIGHT: My name is Ethan Knight, and I'm an Assistant US Attorney for the Department of Justice in Portland, Oregon. And I was one of the two prosecutors in the United States vs. James Nicholson and the United States vs. Nathan Nicholson.

NARRATOR: If you haven’t heard the first part of this story, we’d suggest going back and listening before you settle in for the denouement. But now, let’s rejoin Nathan Nicholson in that airless interrogation room, deep within the Russian Consulate in San Francisco. Nathan hands over his supporting documentation - a picture of himself, alongside his infamous father. The chief of security gives the photograph an impassive once-over.

ETHAN KNIGHT: Obviously the Russians generally are going to be suspicious of someone walking into a consulate, claiming to be an American citizen connected to an imprisoned US spy. 

NARRATOR: Very suspicious indeed. In fact, the Russian turns him away outright but the door is left open, just a crack: “Come back in two weeks.”

ETHAN KNIGHT: And so, it's not surprising or uncommon, generally speaking, that he would be turned away until that information could be verified and he didn't know that. But when he drove back to Portland - up Interstate 5 along our West Coast - he called his dad and, in code, relayed this information.

NARRATOR: In Sheridan Federal Prison, northwest Oregon, Jim Nicholson replaces the receiver. Unlike his son, he’s not in the least bit perturbed by the rejection. It’s a complex game - a long one, too. And nobody plays it better than him.

ETHAN KNIGHT: This was my first foray into espionage. And the reality is there aren't many of these cases brought nationally, and there certainly aren't many brought in the District of Oregon. And lastly, there aren't many that involve former spies.

NARRATOR: In the Department of Justice, Ethan Knight and his colleagues are responsible for prosecuting federal crimes, including cases that impact national security.

ETHAN KNIGHT: We work closely with investigators, usually from the FBI, who bring us the cases, but it's our job to see them across the finish line and to ensure that they are judiciously and successfully handled when they get to court. And helping the FBI make tactical decisions on whether they needed assistance with legal process or any other search warrants to move forward with their case at that time. 

NARRATOR: Need a wiretap? A covert entry? You’d better have permission from the DoJ. Prosecutors like Ethan are made aware of ongoing investigations during the early stages and have oversight across the entire process. But when investigators caught wind of the second generation of Nicholson espionage in 2007, cases of this magnitude were all relatively new to Ethan.

ETHAN KNIGHT: I had arrived at the US Department of Justice just about a year before I became involved in the Nicholson case. I had been a local prosecutor here in Portland, Oregon, handling mostly murder cases, and robbery cases for a district attorney's office. And, roughly a year into my tenure, I got called in and was asked to be involved in what was then a very sensitive case. And that was the early investigative stages of the United States vs. Nicholson. 

NARRATOR: Nathan Nicholson - quiet, blond, and unassuming - was 12 years old when his father was arrested and imprisoned on espionage charges. Overnight, his world had imploded. Jim Nicholson had been nicknamed ‘Batman’ at the Agency for his competence and élan. Nathan, his youngest boy, couldn’t help but cast himself as Robin. Now, all around him, the world decried his hero as a villain. He never quite believed them. And, in the decade between their last farewells outside Dulles International Airport, to the moment he arrived at the Russian consulate in San Francisco, Nathan had walked an unforgiving road.

ETHAN KNIGHT: Nathan he was a young man, probably in search of an identity trying to figure things out. Not in great financial shape and probably trying to sort out his future. 

NARRATOR: With Jim behind bars, money was tight for the Nicholsons. All three siblings had incurred debts. Nathan himself was in the hole for $8,000 in car repayments. Unsuccessful stints as a pizza delivery driver and an insurance salesman had barely made a dent. And his bad luck went beyond his wallet.

ETHAN KNIGHT: I mean, he had had an injury while in the Army that ultimately got him an honorable discharge and disability from the US Army. And I think that set him adrift.

NARRATOR: Later, Nathan would speak of a dark moment in the aftermath of that injury. He had been on the verge of attempting suicide. A call from Jim had interrupted him before he could make a fatal mistake. In a way, he believed that he owed his father his life.

ETHAN KNIGHT: He came back to Oregon, where his family was and where his dad was. But I think the future that he envisioned for himself at that time, like many young folks, suddenly looked different. And I don't think he knew how to reconcile that vision, what he thought was his future, with the reality and where he was at that time. 

NARRATOR: He’d maintained contact with his father since his incarceration, keeping the older man up to speed with the rapid social and technological changes of the era. He had shared his achievements and ambitions, all to a stream of unqualified fatherly praise. As life took chunks out of Nathan, he filled the gaps with Jim’s approval. Meanwhile, Jim Nicholson had been suspected of trying to smuggle messages out of prison for his former handlers in Moscow. Fortunately for Jim, a subsequent FBI investigation was unable to turn up any definitive evidence. But in 2006, with his son back in Oregon, he recognized the potential of having a blameless man-on-the-outside through which to communicate with his erstwhile employers.

ETHAN KNIGHT: He began to meet with Nathan more frequently, talked to him more frequently than his other kids, and began to lay the groundwork for Nathan's initial contact with the Russian Federation at the consulate in San Francisco. So Jim Nicholson was housed in the Sheridan Federal Penitentiary here in Sheridan, Oregon, about an hour and a half outside of Portland. In many ways, a bucolic setting in the rolling hills of Yamhill County. And part of the reason he was there, of course, was to see family and Nathan Nicholson would conscientiously visit him there at Sheridan, in the visiting room. And the visiting room looked both spartan and accommodating. And it was an open space almost like the waiting area of the bus station minus some of the accouterments. And it was there that they would talk in person, face to face. 

NARRATOR: During these father-son catch-ups, Jim Nicholson began the process of recruiting his own son as an asset. As an experienced CIA case officer, it was a dance he knew intimately. And if you’ve listened to previous episodes of True Spies, you’ll already know the steps. A good CO can spend months grooming their target before making their pitch. They’ll learn their likes and dislikes, express interest in their hobbies, and winnow out the essential motivations that drive them. Jim Nicholson had been a highly effective Case Officer. And for him, this was child’s play.

ETHAN KNIGHT: You have to start from the proposition that there's an incredible power dynamic and an emotional power dynamic between the two of them. You're talking about father and son, and that's different than every source I suspect that Jim Nicholson ran in the field and a different dynamic between any two co-conspirators. And sadly, in many respects, in my view, that gave Jim Nicholson a tremendous head start. It gave him a head start because he knew exactly what buttons to push and what to say to bring Nathan along in this game. And the praise he heaped on him was not just the praise of a handler to a source, it was the praise of a father to his son. And it can't be underestimated what that could mean and what it meant to Nathan.

NARRATOR: During their conversations, Jim learned about the financial strain that was facing Nathan, his two siblings, and the rest of the family. And so he proposed a quick, easy, and consequence-free way for his youngest son to raise some funds. If Nathan could make contact with the Russians, they would make sure that the Nicholson clan was looked after. It was a matter of honor between gentlemen, after all - Jim had sacrificed his career, his family, and his freedom for the Kremlin. They would pay up. 

ETHAN KNIGHT: And what Jim had repeatedly told people - and what the facts bear out to some degree - is he's collecting a pension for doing work for a former employer. In this case, the employer wasn't the United States government, it was the country he betrayed them for, and that was the Russian Federation. And so, there's an interest almost as a recruiting tool for folks to know that we take care of our own. And in this case, they meant taking care of Jim Nicholson. 

NARRATOR: Nathan trusted his father implicitly. If he said that this was above board, then he believed him - or he could convince himself that he did, anyway. More to the point, for the boy who had grown up idolizing his superspy father, this was a chance to enter the secret world alongside him. Across the table in the sterile confines of the prison visiting room, Jim taught Nathan the basics - how to detect surveillance, how to communicate securely, and what he could expect when he met the Russians. But, as we know, Nathan’s first trip to the Russian consulate had been underwhelming, to say the least. When he returned, two weeks later, he received a much warmer welcome.

ETHAN KNIGHT: On the second trip to San Francisco, it was characterized later on to me that they were almost apologetic, and he makes it back to the chief of security in the same room. And that's when it appears, at least from the characterization of the meeting, that they do indeed believe him when he says who he is, and that is the son of an imprisoned Russian spy. And at that point, the dialogue and conversation began about: “What can we do? How's the family? And what's going on with your dad?” 

NARRATOR: Clearly, the Russians had allayed their previous doubts about his identity. Nathan left that meeting with $5,000 in cash - a token of goodwill, and a promise of future collaboration. On his way back to Oregon, he called his father at Sheridan prison to share the good news. Speaking in code, Nathan informed Jim that he had cleared an impressive sale in San Francisco. The youngest Nicholson had held a day job as an insurance salesman. Any curious eavesdroppers would sense nothing amiss - unless they had access to Nathan’s actual sales record, which was poor. He also mentioned an upcoming ‘business trip’ to Mexico City. This was also the location of the nearest Russian Embassy away from the FBI’s US jurisdiction. He would fly there in December of 2006, a couple of months away. In the meantime, father and son would start their work in earnest.

ETHAN KNIGHT: Someone listening may say: “Well, how on earth did this prisoner - whose calls and mail are monitored as a condition of his earlier plea agreement - how can he facilitate this?” And you have to go back to that spartan visiting room that we were talking about just a moment ago and realize that he had already scouted out the scene and knew how to slip notes to Nathan that he could take out of the visiting room and deliver by hand to the Russians at any one of these consulates because he knew very well he couldn't simply drop that in the mail. So he was a trusted conduit, Nathan was, to get this information out. 

NARRATOR: If you’re passing notes in a secure environment - a prison’s visiting room, say - you’re going to want to be subtle about it. The ‘brush pass’ is a stalwart piece of CIA tradecraft wherein an item is passed almost imperceptibly between a case officer and his source. It requires confidence, sleight of hand, and years of practice to pull it off. 

ETHAN KNIGHT: And sometimes Jim, leaning close to his son, will either slip them in Nathan's pocket, probably not drawing any attention from guards nearby. If he was giving his son a hug, even though contact was limited, or he'd brush by him and simply drop them in his pocket.

NARRATOR: Nathan, warming to his role, eventually devised an even more ingenious method of communication. He would buy snacks from the vending machine and eat them with his father at the table during visits. When the time came for him to dispose of the empty wrappers, he would pluck another note from beneath the pile, secreted there by Jim during the course of their bonding time. Over time, Nathan came into possession of an impressive, if untidy dossier of secrets plucked from the mind of his spy father. Even with a decade outside of the Agency, Jim Nicholson retained information that would be worth the Russian’s time. For example, any details he could recall about the months leading up to his arrest in ‘96 could hold clues to how the FBI investigated traitors. With that kind of insight, the next generation of turncoats might just get away with it. By December 2006, six weeks had passed between Nathan’s second meeting with the Russians. Mexico beckoned.

ETHAN KNIGHT: Nathan is invited to go to Mexico City, or he's encouraged to go there. He had relayed this to his dad. And there certainly was an element of excitement. And while he was indeed simply a conduit between his father and the Russians, he, in his mind, was also a son who was living the life that his father lived. And there was an element of excitement in what he was doing, the fact he was going abroad. In these subtle acts of deception he was engaged in, and he was making his father proud. And so, against that backdrop, he went to Mexico City and went to the embassy there following the instructions - specifically to ask for the chief of security.

NARRATOR: This time around, Nathan found himself in a large, well-appointed room overlooking a picturesque courtyard. His host, a short, gray-haired man in his early 70s, greeted him graciously.

ETHAN KNIGHT: Nathan said the name of his handler, at least known to him, was George. 

NARRATOR: In reality, ‘George’ was a KGB general who had been brought out of retirement to handle Jim Nicholson’s courier - which should give you some idea of just how valuable this line of inquiry was to the Russians. Nathan handed over a couple of handwritten notes from his father. The SVR man read them approvingly and requested another meeting with Nathan in July of the following year. In the meantime, he was to ask his father the following questions: i) What were the identities of the FBI agents who had interrogated him in 1996? ii) At what stage might he have come under surveillance? iii) Who might have been placed to report his activities to the CIA? And with that, George unloaded $10,000 onto the table in front of Nathan Nicholson. Until next time. Nathan was thrilled. He turned his hat and jacket inside-out, and left the embassy - if he had been followed, he hoped that a swift change of outfit might throw off his tail. That’s True Spy behavior, sure enough. But possibly surplus to requirements.

ETHAN KNIGHT: Nathan, his image of himself, I think, at this stage may be different from reality. He was taking steps that he thought would be helpful or necessary to avoid detection, and reversing his clothes and concealing the cash on him when he left Mexico for the United States were two of those things. 

NARRATOR: Once he was safely back on US soil, Nathan distributed the money between members of his family, claiming that the cash came from his grandparents’ handicraft business. Needless to say, nobody asked too many questions. Jim Nicholson’s boy had done well. The older man heaped more praise on the younger, assuring him that he had handled himself better than many recent graduates of the Farm. Inwardly, Nathan beamed with pride. Six months later, he returned to Mexico City with the information that George had requested along with some ambitious requests from his father.

ETHAN KNIGHT: Jim had, I think, fanciful ideas of what he thought he was going to do or how he was going to get out of prison. Everything from an elaborate escape involving a helicopter to resettling to sell recreational vehicles in the Russian Federation. And these were at least thoughts he had and expressed to others during that time about his long-term planning. And I think at some level, certainly, thought that he would be able to sign the Russians up for any one of these schemes.

NARRATOR: It should probably go without saying that a helicopter extraction from an American prison was not on the cards for Jim Nicholson. But the information he had provided was good. The Russians were happy to keep paying his son, the courier, for more intel. Since being discharged from the Army, Nathan’s stints as a pizza delivery driver and would-be insurance salesman had failed to inspire him. But he was discovering a talent for espionage - one that leveraged his youth to his advantage. When George provided Nathan with an unsecured Yahoo email address through which to communicate, the spy’s son took the elderly KGB man to school. If you grew up in the early 2000s, you might be familiar with this approach to covert contact, which worked on suspicious parents and counterespionage investigators alike.

ETHAN KNIGHT: So they would simply leave electronic messages for one another in draft message folders and then pick them up to confirm whether or not they'd had them, or put a new one and confirm whether or not they'd received them. And that's sort of the process that they followed at the direction of the Russians throughout their time together. 

NARRATOR: As the second layer of security, the emails were written in the same euphemistic style that Nathan had used on phone calls to his father.

ETHAN KNIGHT: There were a series of code names that Nathan had used with the Russians in email form so that they could communicate, at least at that time - we're talking 15 years ago - surreptitiously. This is before the era of easily accessible, encrypted communication platforms, before Snapchat, before Signal, and before Telegram. 

NARRATOR: For example, if either party couldn’t make a meeting, they would leave a draft email that read: “My brother Eugene is ill.” 

ETHAN KNIGHT: The two of them, Nathan and his handlers, were using pseudonyms. And the whole purpose was, of course, to create a fictitious or easily disguised line of communication that would keep anyone interested off the trail. 

NARRATOR: Before Nathan returned to the States, the Russians set up another rendezvous - this time in Lima, Peru - for December 2007. He could hardly wait. So far, things had progressed smoothly for Jim and Nathan Nicholson. But you already know how this story ends. What goes up, must come down - even if it has to be pulled.

ETHAN KNIGHT: You have to look at how, ultimately, the FBI and others were able to determine that indeed, Nicholson was engaged in the same activity again through the prism of examining someone who had not only done this in the past, but also had tried and made efforts to use other inmates to his advantage. Not many years after he'd gone to Sheridan, he was using other inmates to try and get messages out and find ways to circumvent the very clear protocols that were set up. He was under a heightened amount of suspicion. So when those letters were examined, when those calls were examined, all of us were looking at those really from the perspective of: “Is there something else going on?” 

NARRATOR: Jim Nicholson was good at what he did - and he knew it. His communications with his son, while technically unencrypted, were vague enough to avoid suspicion. So it fell to Nathan, merely a talented amateur, to make the first mistake. It was a wonder that it hadn’t happened before now. CIA analysts routinely listened to the Nicholsons' calls and read their letters.

ETHAN KNIGHT: And I think there was one line in a call or a letter, and he sort of slipped and said: “How's that… ‘thing’ going?” And it was just enough of an opening, enough daylight, where that looked different. I think certainly in hindsight, that began to give way to “maybe something else was going on”.

NARRATOR: Nathan had reached for another euphemism and missed. The analysts alerted the FBI.

ETHAN KNIGHT: Well, the FBI, obviously having an interest in this, began to look more carefully at the writings and the letters, and they also began to look more carefully at the earlier efforts that Jim had made to get material out of the prison because that, at least, underscored the belief that he was finding a way or looking to find a way to contact the Russian Federation. And so, going back over those old interviews, into those inmates, and then looking at the new communications with Nathan, obviously prompted some concern that the two of them, Nathan and Jim, were up to something now.

NARRATOR: The Bureau sprang into action. A team was assembled to lead a new investigation into Nicholson and his youngest son. The Department of Justice issued warrants for electronic and physical surveillance on both men. 

ETHAN KNIGHT: Notwithstanding what folks often see on TV, there's no switch you can flip to suddenly be monitoring everyone's calls. It has to go through a very cumbersome and secret process. And in this case, that's what happened. And ultimately, there was a search conducted - authorized by a judge - of the cell, and of Nathan's apartment.

NARRATOR: FBI agents were able to gain access to Nathan’s apartment as well as his car. More than a decade earlier, similar searches had thrown up a mountain of evidence against his father. Now, evidence gathering allowed the Bureau to predict their target’s next moves.

ETHAN KNIGHT: And if you look at the letters that Jim was sending Nathan, that actually referred to specific locations that he said would be good to vacation in. He had mentioned discreet spots in South America like Lima. He had even alluded to Cyprus in a very circuitous way in a discussion about architecture in that part of the world, which, at the time, we began to piece together as recommendations for safe places to conduct meetings. And that helped the FBI begin to get a picture, of course, of what happened, particularly leading up to his trip to Peru.

NARRATOR: By late 2007, communications technology was a different and more sophisticated beast than its mid-90s counterpart. Nathan’s cell phone and computer were easily tapped. But even a monitored line needs someone to, well, actually monitor it.

ETHAN KNIGHT: The FBI was tracking Nathan's car, getting close to it while he was in the middle of his activities with the Russians. At one point, they lost sight of the fact that he had gone to Portland International Airport.

NARRATOR: The call was made at around 4 am on the 10th of December, 2007. Nathan was contacting his girlfriend to tell her that he had safely arrived at Portland International Airport. But nobody at the Bureau was awake to hear it. Four hours later, the agents realized that the GPS tracker on their target’s car was miles away from his home in Eugene, Oregon. By the time their black sedans screeched to a halt outside the terminal, they were much, much too late.

ETHAN KNIGHT: And it was later confirmed that not only had he gone to the airport, but he'd gone to Lima, Peru and the FBI scrambled and missed him, but ultimately tracked him when he came back.

NARRATOR: When Nathan landed on home soil three days later, he was in receipt of another $10,000. His next meeting with his handlers was ordained to take place in the ancient city of Nicosia, on the sun-kissed Mediterranean island of Cyprus. Treachery does have its perks. He had made a note of his destination in a nondescript little notebook. A trained spy would have encoded the information. Nathan was not a trained spy. As he passed through airport security, he was earmarked for a random inspection by customs. Of course, there was nothing random about it. His bags were taken to another room, where the contents were pored over by members of the FBI team.

ETHAN KNIGHT: And that's really when they got some information that gave them tremendous insight into the case. And that was a journal he kept. 

NARRATOR: That telltale notebook, containing spools of unencrypted documentation about Nathan’s work for the Russians, proved to be a goldmine.

ETHAN KNIGHT: And as remarkable as it seemed, he laid out many of the details names, dates, and places in this journal that would help reconstruct what we knew to be, later on, the extended scheme between Nathan, Jim, and the Russians. And they pretty explicitly state the details for an upcoming meeting that he was to have in Cyprus. And, at that time, given what the prior activities had been, agents were relatively certain, of course, that this was indeed the real thing. 

NARRATOR: Once the Bureau agents had what they needed - including the exact address at which the next meeting would take place - Nathan’s possessions were returned to him. No sense in closing the net too soon. On his next visit to Sheridan, the young man explained to his father what had happened. Jim agreed that this was cause for concern, but was willing to take the risk. After all, Nathan’s next rendezvous with the Russians, in Cyprus, was a year away, scheduled for the winter of 2008. There would be plenty of time to mull over their options, and, if necessary, abort the operation before anyone could be charged. In the intervening months, the FBI kept a close watch on Nathan’s communications, including his letters to Jim, and his digital dead drops to the Russians. In November 2008, he was observed at a travel agency, booking a flight to Cyprus. A month later, he was airborne once more. This time, the FBI knew exactly where he was headed.

ETHAN KNIGHT: They were planning on meeting at a TGI Fridays in Cyprus, a restaurant that I thought had closed its doors in about 1989, roughly before the fall of the Berlin Wall, but evidently was still open for business in Cyprus and was the chosen place of meeting for the Russian Federation. I mean, I couldn't believe it. We first got this thing, I thought, really, Fridays?. That's where we're meeting? But don't wanna make it too obvious.

NARRATOR: It was here, at the branch on 12 Diagorou Street, that Nathan met his Russian handler at 7 pm on the 10th of December - exactly a year on from his last appointment. The FBI obtained footage of the meet - hard evidence that the younger Nicholson had committed a crime against his homeland. As the 24-year-old began walking back to his hotel, laden with $12,000 in cash, he was riven with anxiety. The superspy fantasy had given way to the stresses of a man who knew that he could well be standing at the edge of an abyss.

ETHAN KNIGHT: By December of 2008, after Nathan's trip to Cyprus, the gig was clearly up and Nathan flew back into the United States on an unseasonably snowy day. The roads were covered in snow and ice, and it took him a very long time to make that trip from the Portland airport to his home, at that time, in Eugene, Oregon, a small college town about 90 minutes south. He made it there through the storm.

NARRATOR: Exhausted, Nathan Nicholson slept deeply. The end came during the deepest snowfall that anyone could remember. And it came with a knock - a deep, insistent pounding that lurched Nathan Nicholson out of his bed. It was mid-afternoon, with 10 days until Christmas. Half asleep, he shuffled to the door of his bachelor’s apartment, hoping against hope to be greeted by an especially determined Jehovah’s Witness. He opened the door.

ETHAN KNIGHT: Only to be greeted by two FBI agents who, of course, had been immersed in his life and this investigation and the prior case of his father's for months. And they were there and they were ready to talk, much to his surprise. And of course, they knew far more than I think he knew that they [did]. 

NARRATOR: Meanwhile, in a command center nearby, Ethan is braving the cold too.

ETHAN KNIGHT: On that day, Nathan had flown in from halfway around the world. My co-counsel, Pam Holsinger, and I made that icy drive down to Eugene, Oregon, on that very day. It took us eight hours to make it 90 miles on the interstate to be there when the confrontation with Nathan occurred and we were not in the room, but we were there to ensure that everything went as it had been planned logistically and to ensure that we could do everything we could to preserve the information evidence for its ultimate prosecution. 

NARRATOR: For now, the prosecutors can only wait as the FBI enters Nathan’s apartment. It’s the second time in his life that he’s been greeted by men in Bureau suits. The first time, all the way back in 1996, was the worst day of his life. Today is a close runner-up. Finally faced with the consequences of his actions, Nathan decides to lie.

ETHAN KNIGHT: You can see the hamster running on the wheel trying to think: “How can I outsmart this situation? Is there a way out?”

NARRATOR: Nathan and his father have concocted cover stories for each of his travels abroad. Visiting an Army buddy. Finding a nice spot to propose to his girlfriend. Studying architecture. He carried cash because he didn’t trust the banks. It’s 2008 - who would?

ETHAN KNIGHT: And, depending on who's doing the questioning, the further you get into that conversation, the person often will realize there's no way out. And they know too much. Or maybe it's just time to be honest and own up to this. And Nathan got to that point later than some, but sooner than most.

NARRATOR: The FBI listened to Nathan’s fabrications. And then, calmly, they stopped him. They offered him a chance to start over - to tell the truth. To loosen the thick knot of anxiety that had tangled in the pit of his stomach for two stressful years. And he took it.

ETHAN KNIGHT: Nathan appeared, by all accounts, to hold up relatively well. I mean, there's always that aspect when somebody is caught that you can almost see it in their eyes where they have to have been thinking this day was going to come, even if they thought they'd gotten away with it. But he was friendly and he gave them information and he got in the car with those FBI agents and began what would be really a very clear break from his past and a new and different chapter in his life with the initiation of a criminal case against him for engaging in, really sadly, what was conduct similar to that that had gotten his father in prison. He was arrested very soon after and indicted very soon after.

NARRATOR: The Department of Justice moved quickly. They’d spent months gathering evidence. Now they could finally put the prosecution into motion. In Sheridan prison, Jim Nicholson was taken from his cell. 

ETHAN KNIGHT: Ultimately, the charges that were levied against both Nathan and his father were twofold. They were not traditional espionage, but they were that Jim Nicholson and his son were acting as an agent of a foreign power or agents of a foreign power. And that is, they are doing things at the behest of the Russians without authority from their own government and they're laundering money in this case, the proceeds of that activity. So the operating or animating theory of our case had always been that Jim Nicholson was collecting a debt or a pension from the Russian Federation.

NARRATOR: The court proceedings were painful for Nathan.

ETHAN KNIGHT: The first time that we saw Nathan Nicholson, he didn't fit the mold of your typical grizzled criminal. He was nervous and scared and looked like he could have been a juror or somebody watching from the back of the room because the reality is this was not only his first foray into espionage but his first foray into the criminal justice system. And I think the look in his eyes said that the moment we saw him for the first time and when we got to the end of the case, you know that awareness you could see had finally sunk in of the severity of what he'd done and where he was. 

NARRATOR: The defendant was forced to confront some painful home truths.

ETHAN KNIGHT: It was a gradual process, I think, for Nathan to realize what had really happened to him, that he had been manipulated. And, at the end of the day, his dad had run him as a source, not unlike many before him. And that was a process, a gradual one, where he had to come to terms both with the evidence against him and realize the legal predicament he was in, but also realize what his options were and that he really - both legally and personally - had to be his own person in this process, and that the final decision he had to make when he stepped into that courtroom alone to enter that guilty plea had to be his and his alone. And he had to separate from his father. 

NARRATOR: Ultimately, Nathan Nicholson took a plea deal on the condition that he testify against his father in court.

ETHAN KNIGHT: At the end of the criminal case, both Jim Nicholson and his son decided to plead guilty for different reasons. Nathan Nicholson received a five-year probationary sentence and, at the end of the day, we all felt that that was indeed appropriate, given his cooperation against his father and given, really, the person that he had shown himself to be. It certainly couldn't have been easy.

NARRATOR: Understandably, Jim Nicholson garnered less sympathy.

ETHAN KNIGHT: When it came to Jim's sentencing, I don't think a single person was surprised that he might want to say more than a few words. This was someone who - I think you would find little debate - at his core is at the very least a narcissist and someone who may have found fault in anyone but himself in this process. What was remarkable, at least to us at the time, and to me, certainly, is that in listening to him opine about the various things that led him to this point again is that he managed to apologize to the Russians. Not to the country he'd betrayed twice, but to the country he, in his mind, had embarrassed. And that was the Russian Federation. 

NARRATOR: At home in Virginia, John Maguire, the CIA officer who led the first operation against Nicholson, was gobsmacked when he heard the news.

JOHN MAGUIRE: A CIA senior officer told me about that. I didn't know it was going on because I had moved on to do other stuff. I was gone and she called me up and said: “I think you might want to know what Jim has done because I was always thinking about the 24 years he's going to serve.” I think he had to serve 80 percent of that sentence. She explained to me: “He's really done something that was outside the lines - he destroyed his kid.” 

ETHAN KNIGHT: Oftentimes as a prosecutor, you have to suspend your earlier conceptions or beliefs about someone and let the facts guide you. In that case, they did with Nathan, and we think that was the appropriate result. Jim Nicholson, on the other hand, is serving an additional eight-year sentence on top of his earlier sentence for espionage, postponing his release date now until roughly the middle of 2024.

NARRATOR: He’ll be serving that time in ADX Florence, a maximum security facility in Colorado. It’s been home to some of America’s most dangerous criminals and reviled traitors - the Unabomber, Robert Hanssen, and El Chapo, to name a few. If you’re anything like us, you’re curious to discover what happens to a captured spy when they’ve served their time. Well, we can only speculate. But John Maguire has a good idea.

JOHN MAGUIRE: I expect him to be gone in a flash. I hope they're watching it. I hope they [have] surveillance and put the lid on him because he has the skill set. And 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. They honor their commitments just like we do. They owe him money. They'll pay him. 

NARRATOR: Ultimately, justice was served. But when John and Ethan look back on the story of the spy and his son, they can’t help but do so through a father’s eyes.

ETHAN KNIGHT: I reflected periodically throughout the case about what legacy you owe your children and how you should treat them. 

JOHN MAGUIRE: He compromised his bond of trust and responsibility as a dad and used his kid to do something illegal to make money and wrecked his kid's life. I just thought: “I don't know how a father does that as a dad. It just doesn't compute for me.” I mean, you sacrifice your own life to save your kids. You don't sell them and use them to make money. 

ETHAN KNIGHT: And that's the piece of this that can't get lost in the espionage and the role of the Russian government and the gamesmanship that really is inherent in any espionage investigation or case that may be a chess match, but at the end of the day, you have probably a scared little boy whose dad was taken away from him when he was 12 now facing those same demons as an adult. And what does that really mean? And what does he have to do to confront that? 

NARRATOR: I’m Vanessa Kirby. For more details about this extraordinary case, pick up a copy of The Spy’s Son by author and journalist Bryan Denson. We’d also like to thank Bryan for his invaluable assistance during the pre-production stages of these episodes. Join us next time, as we enter the secret and seductive world of honeypots in a three-part True Spies anthology or, if you’re a subscriber to Spyscape Plus on Apple Podcasts, there’s no need to wait: you can listen to it right now.