Soviet master spy and obsessed gambler, created by Ian Fleming as the first Bond villain in his novel Casino Royale. He’s been portrayed in various permutations in three James Bond films. Le Chiffre’s name comes from the French word meaning “cipher” or “number.” According to Fleming’s original novel, British Secret Service records identify Le Chiffre as a displaced concentration camp survivor after World War II who could not remember his name. Since he became a simple number on a list of displaced persons, he took the name Le Chiffre. He eventually becomes a top agent for the Soviet Union, working in the area of southern France and Monte Carlo. His penchant for high-stakes gambling and high-stakes losing (using Soviet funds) comes to the attention of both the Soviets and Western intelligence. The latter enlists James Bond to bankrupt Le Chiffre in one last grand game of chance, believing that this will convince the Soviets to take matters into their own hands and liquidate Le Chiffre before he becomes a source of embarrassment.

In CBS’s 1954 live adaptation of the novel, Le Chiffre is portrayed by Peter Lorre. An American agent nicknamed “Card Sense Jimmy Bond” (Barry Nelson) is sent to Monte Carlo to outplay Le Chiffre at baccarat. With the help of the Deuxième Bureau’s double agent Valerie Mathis (Linda Christian), he succeeds. However, while searching for Mathis, Bond is captured and tortured by the Russian master spy, who is determined to take back a check worth 87 million francs that Bond won at the tables. While Le Chiffre briefly leaves Bond alone while he goes off to search for the missing check, 007 manages to free himself, and he eventually shoots and kills Le Chiffre and one of his thugs.

The same character, albeit in a comic vein, was portrayed by actor Orson Welles in producer Charles K. Feldman’s Casino Royale spoof in 1967. In that goofy film, the Soviet master spy still plays baccarat in Monte Carlo with stolen Soviet funds, but he’s also a magician who practices his tricks right at the table. Le Chiffre is eventually defeated at the baccarat table by Evelyn Tremble / James Bond (Peter Sellers) and later killed by the KGB.

The most realistic portrayal of Le Chiffre was that of distinguished Danish actor Mads Mikkelsen in the 2006 blockbuster reboot of Casino Royale, which introduced Daniel Craig as the newest James Bond. Mikkelsen’s Le Chiffre is a ruthless sponsor of international terrorism, no longer working for the Soviets but affiliated with an international crime organization that is later revealed to be SPECTRE. The film adds a nice touch to the villain: he weeps blood from one of his eyes, a malady caused by a derangement of one of his tear ducts. He also suffers from asthma and uses an inhaler.

This version of Le Chiffre acts as an international investment strategist, and he has secured funds from Steven Obanno (Isaach De Bankolé), an African rebel leader who has been recommended to Le Chiffre by SPECTRE operative Mr. White (Jesper Christensen). Obanno trusts that Le Chiffre will invest his money wisely, with no risk. No sooner is the money secured than Le Chiffre shorts a million shares of the aeronautics company Skyfleet—betting the company’s stock will go down because Le Chiffre’s organization plans to blow up their sophisticated airliner prototype. However, when Bond thwarts that sabotage operation, Le Chiffre is forced to use the remaining hunk of Obanno’s investment to enter a no-limit, winner-take-all game of Texas hold’em poker. Bond tracks him to Montenegro and enters the marathon game, which Le Chiffre must win at all costs. At one point, Le Chiffre has Bond poisoned—sending 007 into cardiac arrest—but he’s saved by Her Majesty’s treasury liaison Vesper Lynd (Eva Green), who reattaches the line to the heart defibrillator that jolts Bond back to life.

In a nail-biting gambling confrontation, Bond eventually beats Le Chiffre, leaving him penniless. But the villain captures Bond and submits him to one of the most gruesome torture scenes ever conceived for mainstream PG-13 audiences—one taken directly from Ian Fleming’s own description in the book. Bond is stripped and tied to a rattan chair, the seat of which has been removed. Le Chiffre then wields a carpet beater, which he continuously twirls and slams into James Bond’s exposed privates. It’s one of those scenes that’s hard to watch, but Craig is brilliant as he fails to give in to Le Chiffre—even managing to laugh as he’s also screaming in pain. Fortunately, Le Chiffre’s failure to pay back the funds he acquired from Obanno comes back to bite him: he’s assassinated before he can kill Bond.