Appearing in both GoldenEye (1995) and The World Is Not Enough (1999), ex-KGB operative Valentin Dimitrovich Zukovsky (Robbie Coltrane) is the roguish but dangerous head of the Russian mafia, the only competition to Alec Trevelyan (Sean Bean) aka Janus Crime Syndicate. Prior to the events of GoldenEye, Bond shot Zukovsky in the knee, then stole his car and his girlfriend. This creates an air of tension when 007 (Pierce Brosnan) returns to Russia searching for information.
Bond tracks down Zukovsky in his St. Petersburg nightclub looking for intel on Janus. Zukovsky maintains a vast knowledge of firearms — he can discern 007’s presence just from the cocking of his gun. (“Walther PPK, 7.65 millimetre. Only three men I know use such a gun… I believe I’ve killed two of them.”). Zukovsky is wary of helping Bond, but 007 reminds him that he only shot Valentin in the leg, even though he had a clear shot. The pair, realising they have similar aims, broker an uneasy truce: inexchange for the sale of C4 explosives where Zukovsky will be allowed to take the majority of the profits, Zukovsky tells Bond what he knows about Janus and facilitates an introduction.
Years later, in The World Is Not Enough (1999), Zukovsky moves to Baku, seemingly setting up as a legitimate businessman, opening his own casino and caviar factory. He still has some underhand dealings in his portfolio, including a transaction with oil heiress Elektra King (Sophie Marceau). He smuggles Russian equipment and supplies, using his nephew Nikoli (Justus Von Dohnanyi) and a submarine.
When Zukovsky realises Elektra and her lover Renard (Robert Carlyle) have killed Nikoli, Valentin is furious and he goes to find Elektra to demand Nikoli’s hat back, Elektra uses the hat to hide a gun and shoots Valentin. His last act is to fire a rifle hidden in his silver-handled walking cane at a wrist restraint constricting 007, freeing Bond from Elektra’s torture chair. In an ironic twist, the walking stick Valentin uses as a result of Bond’s bullet to his knee saves 007’s life.