updated 1/18/2011 7:40:28 PM ET 2011-01-19T00:40:28

One of the highest-ranking CIA officers ever convicted of espionage will spend eight more years in prison after pleading guilty to betraying his country a second time.

U.S. District Court Judge Anna J. Brown sentenced Harold "Jim" Nicholson on Tuesday in Portland federal court on charges of conspiracy to act as an agent of a foreign government and conspiracy to commit money laundering. Five other charges were dropped as part of the plea deal.

Nicholson admitted to using his son, Nathaniel, to collect a "pension" from Russian agents while serving time in federal prison in Oregon.

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Before his sentence was handed down, Jim Nicholson delivered a tearful confession in court in which he partly acknowledged his transgressions and apologized to his Russian contacts, his parents and his children.

At times choked up, Nicholson said the impetus to collect his so-called "pension" was desperation. Penniless after a previous conviction, he said he sought to help his children with their student loans and debt.

Instead, he drew one of them into his conspiracy.

Nicholson's youngest son, Nathaniel Nicholson, was sentenced in December to five years on probation after making a deal with prosecutors to help build the case against his father, whom the younger Nicholson said he once idolized.

"I love him dearly, I could not be more proud of him," Jim Nicholson said about Nathaniel. "He has never let me down, and he has never failed his family.

"My failure has been mine alone."

During Jim Nicholson's statement, Nathaniel teared up and rested his head against a family member's shoulder.

As part of a deal he struck with prosecutors, Jim Nicholson was given 10 minutes of relative privacy with his family, during which he was prohibited from touching them. U.S. Marshals were instructed to be present in court and listen in on the conversation.

Nathaniel Nicholson declined to comment after the sentencing.

Brown, the judge in the case, said Nicholson could have been released in June 2017, at the age of 66. Instead, he'll be in prison — and likely remain in solitary confinement — until at least 2025. She described Nicholson's statement as eloquent, but challenged whether he regretted his actions.

"Notably absent from his remarks was any suggestion of remorse," Brown said.

Jim Nicholson admitted to using his son to collect more than $47,000 from Russian officials in Mexico, Peru and Cyprus for past spy work.

As part of his plea deal, Nicholson had to agree that prosecutors could prove the facts of the case, which began in the summer of 2006 when Jim Nicholson urged Nathaniel to contact the nearest Russian consulate.

Between October 2006 and December 2008, he met with representatives of the Russian Federation six times, including twice at a consulate in San Francisco.

"Nathaniel was excited about the prospect of acting in a clandestine fashion like his father," prosecutors wrote in a sentencing memo.

Jim Nicholson was divorced while still a CIA agent and had sole custody of his three children. After his conviction in Virginia, the children went to live with Jim Nicholson's parents in Eugene, Ore. Nathaniel Nicholson was 12 when his father was convicted.

He received a medical discharge from the U.S. Army in 2004 when he suffered a back injury during a parachuting training exercise. He began to attend Lane Community College, with the eventual goal of getting a degree in architecture.

At the first meeting at the Russian consulate, Nathaniel Nicholson presented three pieces of paper slipped to him in prison by his father. They included a letter of introduction, a photograph of Jim and Nathaniel Nicholson at the prison, and a request for money.

If caught visiting the consulate, Nathaniel told prosecutors he had a cover story: He would say he was asking the Russians about architecture.

At a second meeting at the consulate, Nathaniel received $5,000 in $100 bills, according to his plea agreement.

That set off Nathaniel Nicholson's globetrotting tour, which included stops in Mexico City, where he met with Vasiliy Fedotov, known to the FBI as a former high-ranking officer with the KGB. Fedotov gave Nathaniel Nicholson $10,000 in $100 bills.

Jim Nicholson told Nathaniel to distribute the money among his grandparents and siblings, and not to deposit more than $500 at a time.

"Nathaniel always took strength from the notion that he was helping the family by following his father's bidding," prosecutors wrote in a sentencing memo.

All along, CIA agents were keeping track of Nathaniel Nicholson, bugging his car, tapping his phone lines and monitoring his e-mails. He was arrested in 2008.

In his plea agreement, Jim Nicholson and prosecutors agreed to stick to the terms of his original agreement, struck in Virginia in February 1997.

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In that deal, for which Nicholson is already serving 24 years in prison, he admitted to providing the post-Soviet intelligence service of the Russian Federation with national defense information, including photographic negatives, between June 1994 and his arrest on Nov. 16, 1996.

Nicholson met with them in several southeast Asian countries, as well as Switzerland, receiving cash payments each time.

When he was arrested at a Washington, D.C., airport, Nicholson was headed to Zurich with cash and information on the identities on the CIA Moscow chief and his staff, the identities and code names of CIA informants and the identities of CIA case officers. He also admitted plans to reveal the extent of U.S. knowledge about the intelligence capabilities and military preparedness of the Russian Federation.

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