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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 the secondary antagonist of the 1963 James Bond film From Russia with Love. He is an assassin who works for SPECTRE.

He was portrayed by the late Robert Shaw.

Biography

Red Grant, also known as 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.

In Ian Fleming's novel, Grant is also a serial killer who preys on young women; his fits of bloodlust coincide with the full moon. SPECTRE knows about Grant's pathology, and allows him to kill innocent people as a "reward" for fulfilling his duties.

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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           007|Villains

Main Villains
Julius No | Ernst Stavro Blofeld | Rosa Klebb | Tov Kronsteen | Auric Goldfinger | Emilio Largo | Dr. Noah | Dr. Kananga | Francisco Scaramanga | Karl Stromberg | Hugo Drax | Aris Kristatos | Kamal Khan | General Orlov | Maximillian Largo | 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

Supporting Villains
R.J. Dent | Miss Taro | Annabel Chung | Red Grant | Oddjob | Pussy Galore | Kisch | Mr. Ling | Denise | Sydney | Mr. Solo | Jed Midnight | Jack Strap | Jill Masterson | Capungo | Fiona Volpe | Vargas | Count Lippe | Jacques Bouvar | Osato | Helga Brandt | Hans | Irma Bunt | Grunther | Wint and Kidd | Bambi and Thumper | Tee Hee | Baron Samedi | Whisper | Solitaire | Rosie Carver | Jaws | Liparus Captain | Naomi | Sandor | Professor Markovitz | Dr. Bechmann | Chang | Erich Kriegler | Emile Locque | Hector Gonzales | Claus | Apostis | Fatima Blush | Octopussy | Gobinda | Mischka and Grischka | Magda | Scarpine | Hans Glaub | May Day | Jenny Flex | Pan Ho | Bob Conley | Necros | Imposter 00 | Dario | Milton Krest | Ed Killifer | Heller | Perez | Xenia Onatopp | Arkady Ourumov | Boris Grishenko | Richard Stamper | General Chang | Henry Gupta | Dr. Kaufman | Captain Scott | Timblin | Satoshi Isagura | Tom Wallace | Philip Jones | Jeff Hobbs | Mary Golson | Beth Davidson | Tamara Steel | Gabor | Sasha Davidov | Mr. Bullion | Giulietta da Vinci | Mikhail Arkov | Trukhin | Lachaise | Miranda Frost | Tang Lin Zao | Mr. Kil | Vladmir Popov | Dr. Alvarez | General Li | General Dong | General Han | Van Bierk | Mr. White | Steven Obanno | Vesper Lynd | Valenka | Alex Dimitrios | Adolph Gettler | Dryden | Kratt | Mollaka Danso | Carlos Nikolic | Leo | Fisher | Luiz Medrano | Colonel Carlos | Gregg Beam | Elvis | Lieutenant Orso | Craig Mitchell | Yusef Kabira | Edmund Slate | Marchetti Pilot | Guy Haines | Gregor Karakov | Moishe Soref | Severine | Patrice | Boat Captain | Max Denbigh | Mr. Hinx | Marco Sciarra | Moreau | Dr. Vogel | Guerra | Abrika | Marshall | Valerian | Lorenzo | Gallo | Francesco and Marco

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

Organizations
The Union | SMERSH | SPECTRE (Quantum & Greene Planet) | Auric Enterprises (Flying Circus) | Stromberg Shipping Line (Liparus Crew) | Zorin Industries | Janus Syndicate | Carver Media Group Network (Stealth Ship Crew)