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Leave no witnesses.
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Riley is the lawyer for Alexei Volkoff, and handles Volkoff's interests after his boss is arrested and incarceration. Riley first meets Vivian when he reads her father's letter of intention for her to take control of his company, Volkoff Industries. He is portrayed by Ray Wise, and is the tertiary antagonist of Season 4.
Riley is adamant that Vivian accept the directive to become her father's successor, and holds her at gunpoint when she declines. Although Vivian injures him and escapes, Riley later returns her locket and convinces her that the CIA have manipulated and betrayed her, revealing that Chuck, the man she trusts, was the agent who arrested and incarcerated her father. When Chuck promises to try and help her see Volkoff, but is blocked by the CIA, she decides that it was Chuck who lied to her, not his superiors, and this opens her up to be willing to listen to Riley who then poisons her mind against Team Bartowski.
In Chuck Versus Agent X, Riley and Jasmine, attempt to recover Stephen Bartowski's laptop, ambushing Chuck and his friends during his bachelor party in Las Vecas, and later assaulting Team Bartowski at the Somerset home of Hartley Winterbottom; the real identity of Alexei Volkoff aka Agent X, so they can retrieve deep intelligence on Agent X from Hartley's mother. Riley survives when Mrs. Winterbottom destroys the house and kills Jasmine and the assault team.
Riley returns in Chuck Versus the Last Details, guiding Vivian into becoming Volkoff 2.0; ruthless, merciless, cold. Riley and Vivian capture Frost as she attempts to retrieve the Norseman Device. Riley tells Vivian that Frost betrayed her father. Frost then escapes with the help of Team Bartowski, but Chuck let slip in front of Vivian and Riley that Frost is his mother.
By the end of the episode, Riley and Vivian attempt an escape, but their car is rammed in order to stop them and allow Chuck and Sarah to capture them along with the Norseman Device. Chuck again tries to reason with Vivian, telling her that he is not Agent X, and that Agent X is actually her father. Riley holds Chuck at gunpoint and lies to Vivian, to further push her toward the merciless CEO he is trying to form, and tells her it was Stephen Bartowski who turned her father into Volkoff, "Are you going to tell her who turned her father into Alexei Volkoff, huh? It was Stephen J. Bartowski. Chuck's father. He and Frost manipulated your father to give up his own identity so they could further their CIA careers." Chuck hotly called this the lie it was, and Riley then tried to kill him. Sarah shot Riley, saving Chuck, but Vivian got away, Riley's lies still the basis for her actions.