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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.

Donald "Red" Grant is an assassin working for SPECTRE who is the secondary antagonist of the film From Russia with Love.

He was portrayed by the late actor Robert Shaw who has also portrayed Mr. Blue/Bernard Ryder and Doyle Lonnegan.

Biography

Red Grant, aka Donald Grant , works for SPECTRE and is assigned the task of assassinating James Bond to avenge the death of Dr. Julius No.

The pre-title sequence in From Russia with Love shows Bond and Grant searching for one another. In the end 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 presumably incarcerated for life) and was recruited by SPECTRE in Tangier, while on the run from the law. He has been intensively trained by the organisation and when not on a mission, he resides 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 Bond delivers (unknowingly) the Lektor encoding device into SPECTRE's hands. Grant is killed on the Orient Express when Bond outsmarts him with the use of Q-branch's attaché case, and strangles Grant with his own garotte.

Videogame appearance

In the video game based on the novel and film, Red Grant is the chief enforcer for the terrorist organization OCTOPUS. He has a female assistant named Eva. Grant does most of OCTOPUS' dirty work, but his primary mission is to kill 007 and acquire the Russian Lektor decoding device. He catches up with Bond on the Orient Express and attempts to kill him. Unlike the novel and film, he survives the confrontation unbeknownst to Bond. During the agent's final assault on OCTOPUS' island headquarters, he attacks Bond again, but this time is killed.

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Main Villains
Julius No | Ernst Stavro Blofeld | Rosa Klebb | Auric Goldfinger | Emilio Largo | Dr. Noah | Dr. Kananga | Francisco Scaramanga | Karl Stromberg | Hugo Drax | Aris Kristatos | Kamal Khan | General Orlov | Max Zorin | Georgi Koskov | Brad Whitaker | Franz Sanchez | Alec Trevelyan | Elliot Carver | Elektra King | Renard | Gustav Graves | Le Chiffre | Dominic Greene | Raoul Silva | Ernst Stavro Blofeld

Henchmen
R.J. Dent | Miss Taro | Annabel Chung | Red Grant | Kronsteen | Krilencu | Oddjob | Pussy Galore | Kisch | Jill Masterson | Fiona Volpe | Vargas | Jacques Bouvar | Osato | Helga Brandt | Hans | Irma Bunt | Grunther | Wint & Kidd | Bambi & Thumper | Tee Hee | Baron Samedi | Whisper | Solitaire | Rosie Carver | Nick Nack | Jaws | Naomi | Sandor | Chang | Erich Kriegler | Emile Locque | Hector Gonzales | Claus | Apostis | Fatima Blush | Octopussy | Gobinda | Mischka & Grischka | Magda | May Day | Hans Glaub | Scarpine | Jenny Flex | Necros | Imposter 00 | Dario | Milton Krest | Ed Killifer | Heller | Perez | Arkady Ourumov | Xenia Onatopp | Boris Grishenko | Stamper | Henry Gupta | Dr. Kaufman | Giulietta da Vinci | Gabor | Miranda Frost | Zao | Mr. Kil | Mr. White | Steven Obanno | Gettler | Valenka | Vesper Lynd | Kratt | General Medrano | Craig Mitchell | Severine | Patrice | Max Denbigh | Mr. Hinx | Marco Sciarra | Dr. Vogel

Video Game Villains
Nigel Bloch | Raphael Drake | Makiko "Kiko" Hayashi | Armitage Rook | Nikolai Diavolo | Katya Nadanova

Organizations
SMERSH | SPECTRE | Quantum | Janus