Red Grant

"My orders are to kill you and deliver the Lektor. How I do it is my business. It'll be slow and painful...The first one won't kill you. Not the second. Not even the third. Not till you crawl over here and kiss my foot!"

- Grant before fighting Bond.

Red Grant is the secondary antagonist in the James Bond novel and film From Russia With Love. He was played by actor Robert Shaw.

Novel Biography
Grant is sent by SMERSH superior, Rosa Klebb, to intercept James Bond while safeguarding their pawn Tatiana Romanovain the Balkans. Grant encounters Bond aboard the Orient Express posing as an agent sent by M named Norman Nash. He puts a sleeping pill in Tatiana's drink to knock her out before holding Bond at gunpoint. He is eventually killed by Bond while on the train.

Film Biography
Donald "Red" Grant is a henchman for the villain Rosa Klebb. In the film Grant works for S.P.E.C.T.R.E. and is assigned the task of assassinating James Bond to avenge the death of Dr. Julius No. The pre-title sequence shows Bond and Grant searching for one another. Grant kills Bond, before a mask is removed from "Bond's" face to reveal that the whole thing was a training mission for Grant. Grant is described as being a homicidal maniac, who escaped from Dartmoor prison where he was incarcerated for life and was recruited by SPECTRE in Tangier while on the run from the law.

Grant has been intensively trained by the organization and when not on a mission, he is on SPECTRE Island. Although it's Grant's mission to kill Bond, the early part of the film shows Grant taking on the role of Bond's protector to ensure that Bond delivers the Lektor encoding device into SPECTRE's hands.

Posing as Captain Nash of the British Secret Service, Grant contacts Bond onboard the Orient Express. He tells Bond that he is tasked with smuggling Bond over the border. While eating dinner with Bond and Tatiana, he puts something in Tatiana's drink, which knocks her out on the way back to the compartment. Immediately after Tatiana faints, Bond pulls his gun at Grant, demanding to know why he poisoned Tatiana but Grant calms Bond by telling him that his escape route is only for one and asks Bond if he is after the girl or the Lektor. While explaining his escape plan to Bond on a map, Grant knocks out Bond. While he searches Bond, Bond regains consciousness. Grant threatens Bond with Bond own's gun, revealing to his captive that he is not working for SMERSH but for SPECTRE. Bond tries to reason with Grant, telling him that the Secret Service will double the price SPECTRE pays him, but Grant ignores him, instead telling him how exactly he will kill Bond.

Grant is killed when Bond outsmarts him with the use of Q-branch's attache case, causing him to drop his gun, and strangles Grant with his own garrote after a fistfight on the train.

Videogame appearance
In the video game based on the novel and film, Red Grant is the chief enforcer for the terrorist organization codenamed OCTOPUS. He has a female assistant named Eva. Grant does most of OCTOPUS' dirty work, but his primary mission is to acquire the Lektor decoding device and kill Bond. He catches up with Bond on the Orient Express, and survives the confrontation unbeknownst to Bond. During the final assault on OCTOPUS headquarters, he attacks Bond again, but this time he is killed.