( CNN ) -- The prison sentence for the highest-ranking CIA officer ever convicted of espionage should grow significantly Tuesday when a federal judge penalizes him for continuing his covert activities while incarcerated . According to the U.S. District Court of Oregon website , Harold James `` Jim '' Nicholson will be sentenced -- again -- at 1:30 p.m. ( 4:30 p.m . ET ) in Portland after admitting to working through his son to secretly pass information to and get payments from Russia . The elder Nicholson received a 23-year sentence in 1997 after pleading guilty to spying for Russia , one year after he was arrested at Dulles International Airport outside Washington while attempting to board a flight to Switzerland . Federal prosecutors said that at the time of his arrest , Nicholson was carrying 10 rolls of film of classified documents as well as coded messages on a computer disk . They said he planned to meet his Russian handlers , who would pay him more than $ 180,000 . But his covert , and profitable , relationship with the Russians did not end while he was imprisoned at the Federal Correctional Institution in Sheridan , Oregon . Nicholson admitted as much in November , when -- 21 months after being indicted again -- he pleaded guilty to conspiracy to act as an agent of a foreign government and conspiracy to commit international money laundering as part of an agreement with federal prosecutors . At that hearing , the 16-year former CIA station chief confessed to working with his son , Nathan , to funnel information to and get money from the Russian government between 2006 and December 2008 . Nicholson could have faced 25 years in prison and $ 750,000 in fines for both crimes . But instead , he will have eight years tacked onto his existing sentence per the plea deal , a statement from the U.S. Attorney 's office in Oregon said . According to court documents , Nathan Nicholson , 26 , cooperated with prosecutors in their case against his father after FBI agents confronted him about frequent international travel . The younger Nicholson , a former U.S. Army paratrooper , admitted to authorities during the FBI questioning that he had not gone overseas to visit `` a battle buddy '' as he had claimed previously . FBI agents then informed Nicholson that lying to them was a federal crime and offered him a chance to change his story , according to one agent 's testimony . At that point , FBI Special Agent John Cooney testified , Nicholson became more `` forthcoming . '' Nathan Nicholson told the agents that at his father 's behest , he made trips to California , Mexico , Peru and Cyprus , where he met with Russian government representatives who gave him payments totaling more than $ 35,000 in cash . During Nathan Nicholson 's prison visits to his father , according to court records , `` Harold Nicholson spent a significant amount of time advising ( the ) defendant on how to conduct himself in a clandestine manner as he traveled to and from various international meeting locations . Harold Nicholson tried to impart his CIA training to ( the ) defendant . '' Prosecutors alleged the Russians gave the elder Nicholson back-pay for his prior espionage activities and for details on how he was caught . `` The Russian Federation was specifically interested in how Harold Nicholson got caught by the FBI , '' according to a government sentencing memo filed with the court . It added that the information concerned `` who interrogated him after his arrest and the timing of his transfers as a CIA Officer prior to his arrest . '' According to court records , the elder Nicholson and his son put the plot into motion after Nathan Nicholson complained to his father about the family 's precarious finances . The sentencing memo said that Nathan Nicholson provided crucial help in the prosecution of his father . The elder Nicholson pleaded guilty on the day that his trial was set to have begun last month and who now faces an additional 20 years in prison . In an October psychological report entered into the court record by prosecutors , Nathan Nicholson took aim at his ex-spy father . `` I was n't aware of his selfish side , '' Nathan Nicholson said , according to the records . `` I allowed myself to be blindsided . I was like a lobster in a pot , heated slowly until it was too late . '' CNN 's Patrick Oppman contributed to this report .
' ` ` Jim '' Nicholson will be sentenced Tuesday , again , for espionage . He is continuing his covert activities while imprisoned in Oregon . He could have gotten nine years , but through a plea bargain , he 'll receive two more . The former CIA station chief previously got 23 years for spying for Russia .