Le Chiffre

"You know, I never understood all these elaborate tortures. It's the simplest thing... to cause more pain than a man can possibly endure.... And of course, it's not only the immediate agony, but the knowledge... that if you do not yield soon enough... there will be little left to identify you as a man. The only question remains: will you yield, in time?"

- Le Chiffre, about to torture James Bond.

Le Chiffre is the main antagonist of the Ian Fleming's first James Bond novel Casino Royale, the 1954 television adaptation, and the 1967 and 2006 films of the same name. His alias is French for "The Cipher" or "The Number".

In the novel, not much is known about Le Chiffre's origins, except that he was found in the Dachau displaced persons camp in the US zone of Germany in 1945, before being transferred to Alsace-Lorraine and Strasburg three months later with a stateless passport. He adopted his moniker as he considered himself 'only a number on a passport'. He is the paymaster of a French trade union secretly controlled by the Soviet agency SMERSH.

In the 2006 film, Le Chiffre was born Jean Duran and is Albanian by birth (though officially stateless), and his one notable physical feature was a defective tear duct, which causes him to cry blood. He works for a mysterious group called Quantum, and finances terrorist groups by investing millions of dollars and forcing stock market shifts through terrorist acts. It is implied that he profited off the terrorist attacks on September 11, 2001.

He was portrayed by Peter Lorre in the 1954 television adaptation, Orson Welles in 1967 film, and by Mads Mikkelsen in the 2006 film, who also portrays Rochefort in The Three Musketeers (2011), Hannibal Lecter in the NBC television series Hannibal and Kaecillus in Doctor Strange (2016).

Novel Biography
Le Chiffre is the paymaster of Syndicat des Ouvriers d'Alsace (Alsatian Workmen's Union), a trade union run by SMERSH. He makes a major investment into a string of brothels with SMERSH's money, which ends badly after prostitution is banned. In order to reclaim his lost funds, Le Chiffre travels to Royale-les-Eaux and hosts a high stakes baccarat game with the goal of earning fifty million francs. Secret Service agent James Bond is sent to take part in the game and bankrupt Le Chiffre. Things do not bode well for 007 when Le Chiffre manages to clean Bond out of his funds, but CIA agent Felix Leiter gives him 32 million francs, putting Bond back in the game. Despite one of Le Chiffre's henchman's attempts to kill Bond, Bond wins the game and costs Le Chiffre 80 million francs belonging to SMERSH.

In a desperate attempt to get the money back, Le Chiffre kidnaps Bond and his love interest, Vesper Lynd, and subjects the former to torture, threatening to kill them both if he is not told the location of the money. When he realizes that Bond will not talk, Le Chiffre prepares to castrate him, only to suddenly be shot by a SMERSH agent for his failure.

Airline Scheme
Le Chiffre's first scheme presented in the movie is an attempt to make money for Quantum by investing $101,206,000 that terrorist Steven Obanno had entrusted to Quantum by investing it in an airline company called SkyFleet. His plan was to gamble on the stock by purchasing put options and then ordering the destruction of their new prototype plane. The destruction of the plane was foiled by MI6 agent James Bond, who had come across the plot while investigating what turned out to be some of Le Chiffre's underlings. Le Chiffre lost his total investment, and to save his own skin, he set up a high stakes hold 'em poker tournament at a casino in the Balkan nation of Montenegro.

The Poker Tournament
MI6, who knew Le Chiffre was funding terrorism but couldn't prove it, dispatched Bond to Montenegro to compete in the exclusive tournament, because he was known as the best card player in the agency. Recognizing the threat that Bond posed, Le Chiffre ordered his girlfriend, Valenka to poison Bond on the first night of the tournament, but Bond managed to save himself with a defibrillator, with the help of his treasury contact and love interest Vesper Lynd. Later that night, Obanno and some of his underlings visited Le Chiffre, threatening his life and that of his girlfriend Valenka if he didn't get his money back. The next night, Bond ended up winning the tournament with the help of CIA agent Felix Leiter. He sent the money into an account with a password known only to him.

Death
In a last act of desperation, Le Chiffre kidnapped Vesper, presumably unaware that she was in fact a reluctant double agent for Quantum trying to secure her boyfriend's safety. He managed to capture Bond, and took him to a ship nearby. Le Chiffre wanted Bond's account password, so he tortured him by flagellating his testicles with a weight attached to the end of a rope. Bond refused to give in easily, taunting Le Chiffre that without the password, his clients would find him and kill him for losing their money. However, Le Chiffre gloated that even if he killed Bond and Vesper, MI6 would welcome him with open arms and grant him asylum in return for what he knew, declaring that he would win either way. Bond still refused to give in, so Le Chiffre threatened to castrate him. However, Mr. White, Le Chiffre's immediate superior in Quantum, broke into the room and shot Le Chiffre in the head; partly for having made a deal with Vesper Lynd to save Bond's life in exchange for the money, but also because Le Chiffre could no longer be trusted.

In Spectre, it was revealed that Quantum was a subsidiary of SPECTRE, making Le Chiffre an agent of the latter organization.