On a Saturday morning in the summer of 2006, as the sun climbed over the farmlands of northwest Oregon, Nathan Nicholson drove from his apartment in Eugene to a federal prison two hours away in Sheridan to visit his father, Harold "James" Nicholson, the highest-ranking CIA officer to be convicted of spying.

The visit was a fortnightly ritual for Nathan, one that had punctuated the last decade of his life, from adolescence to the threshold of manhood. Sitting behind the wheel of his blue Chevy Cavalier, he glanced at himself in the rearview mirror. His face was boyish, handsome, with blue eyes and blond hair mowed down to a crew cut. As he sped along Pacific Highway West, which cuts a near-straight path through lush green flat country, he had occasion to reflect upon a lost dream.

In the mirror, Nathan would have liked to see the man he'd always aspired to become: a confident Army Ranger—the spitting image of his father, Jim Nicholson, decades before. Instead, Nathan saw a 22-year-old Army washout, a young man who had failed Ranger training and had left the military without ever having stepped onto a battlefield. While his friends were fighting wars in Iraq and Afghanistan, sending back pictures of themselves in tanks and Humvees, Nathan was studying drafting at a community college and working at a Pizza Hut. There was an ignominy in this contrast, this chasm between what Nathan could have been and what he had become. The only escape from it was the fantasy world of video games in which Nathan immersed himself, sometimes in the company of cousins who lived nearby, sometimes alone. In this world, Nathan could be a hero, vanquishing digital enemies with deft toggles of a joystick and rapid clicks of a mouse.

In a jail cell at the Federal Correctional Institution in Sheridan, Jim Nicholson groomed himself in front of a mirror, as he did every other Saturday in anticipation of his son's visit. As a star agent for the CIA, he had once donned suits and worn a Rolex. Now his wardrobe consisted of prison fatigues that draped his six-foot-tall frame with indignity. Such was the price of betraying one's country: ten years of life taken away, thirteen more to go. The time in prison had aged him. At 55, his beard was flecked with gray, which he took care to mask—especially before meeting his son—with the help of an old toothbrush and shoe polish. In the grand scheme of things, it would prove to be a minor deception whose only aim was to preserve, in Nathan's eyes, his image as a debonair father, international man of mystery.

Jim Nicholson was one of 2,000 convicts at Sheridan, a minimum-to-medium security prison that could pass for a sternly fortified boarding school. Outside the low-slung buildings, inmates grow rows of lettuce and tend rosebushes. Inside, the visiting room looks like a Greyhound bus terminal, with rows of blue plastic chairs and flat fluorescent lights. Vending machines hum on one side, behind a line that prisoners aren't allowed to cross. On his visits, Nathan would walk over that line to get things for his dad: a Twix bar, a hamburger. There were other favors, too: buying Christmas presents for his dad's old friends, sending Nicholson a P. G. Wodehouse novel. But none of these would compare to the task his father had in mind today.

Father and son sat shoulder to shoulder, and the conversation inevitably turned to a familiar topic: the family's financial troubles. Nathan still owed eight grand on his Cavalier. His sister, Star, shouldered $50,000 in student loans, and Jeremiah—the oldest of Nicholson's three kids—was $25,000 in debt. As they spoke, Nicholson leaned into his son. He said he'd thought of a way to help the family from prison. It involved contacting his "old friends"—the Russians—who owed him some money. His plan would require Nathan to do something that was dangerous but not illegal. Would he be willing?