Bentley and Matheson went through CIA Officer training together at Camp Peary. A tutor named Andrea was brought in to help them learn Russian, who Matheson married and had two children with named Russell and Melanie. When he officially joined the CIA, Wilson became his partner.
Hunt for Bentley
Following Bentley's capture by the KGB, Matheson was sent out to rescue him. Matheson found Bentley in a bar in Budapest, Hungary, and Bentley claimed to need immediate exfiltration to escape from KGB pursuers. However, when Matheson arrived at the rally point it turned out to be a KGB ambush; Bentley betrayed Matheson and allowed the KGB to capture him, as Bentley had been brainwashed.
Matheson was then taken before Bentley to be tortured. Although he tried to reason with Bentley and get him to remember his former allegiance, Bentley had no recollection of Matheson and proceeded to torture him for information regarding the whereabouts of Dan Ellender, Kurt Jenkins, and Kay Newman. After Bentley was done with him, Matheson was taken to Dr. Meisner's new lab in Bucharest, Romania, to be trained as a Cicada just like Bentley.
Bentley was eventually taken back to Meisner's lab in Budapest after he regained his senses and shrugged off the brainwashing. He was placed in a cell with Matheson and offered to help him escape, but Matheson immediately reported Bentley to the guards. Their roles have now reversed; Matheson is brainwashed and Bentley tried and failed to reach out to him.
After the guards subdued Bentley, Dr. Meisner placed a disassembled gun and a single bullet before Bentley and Matheson to see "who is truly the best", and then left for them to kill each other. Matheson immediately grabbed for the gun and began to assemble it, and although Bentley tried to stop him, he was only able to take the bullet from Matheson before he finished assembling the gun. Bentley implored Matheson to work with him, but when Matheson continued to fail to remember anything, Bentley took the gun from him and pointed it, now loaded, at Matheson.
After bringing up several facets of Matheson's past and family without effect, Bentley gave him an ultimatum; remember or die. To the very end Matheson couldn't remember, and so Bentley shot the wall right next to his ear, at which point he finally managed to remember bits and pieces of his old life, such as his wife telling him to "get home safe". With enough memories to recognize Bentley, Matheson worked with him to fight their way out of the facility. They rescued a Spanish Cicada along the way, and encountered Meisner himself near the exit. Meisner continued to toy with Bentley, who refused to shoot him despite Matheson's urging, until eventually Matheson himself shot Meisner in the head, killing him.
Stopping briefly in Alexandria, Romania, Bentley shared his concerns with Matheson that killing Meisner and returning to the CIA was all intended by the KGB. Matheson brushed this off as Meisner being a psychopath, "still in your head". Matheson also took note of Bentley's relationship with Petra, saying he'd kill Petra if he ever saw her again. Matheson then returned with Bentley to the CIA Station in West Berlin.