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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.

Donovan/Donald "Red" Grant is the secondary antagonist of the 1957 James Bond novel From Russia with Love and its 1963 film adaptation.

He is an assassin who works for SPECTRE who was tasked to kill James Bond and deliver a Lektor to his superiors. Grant is considered as one of the most famous James Bond henchmen of all time, alongside Oddjob and Jaws.

He was portrayed by the late Robert Shaw, who also played Mr. Blue in The Taking of Pelham One Two Three.

Novel Biography[]

Red Grant is a ruthless assassin working for SMERSH, well-known for his effectiveness and brutality. His bloodlust is not limited to his job; he frequently flies into fits of homicidal mania and kills young peasant girls. His superiors are aware of his "hobby", and provide him with victims as a reward for carrying out especially dangerous missions.

Grant is sent by SMERSH superior, Rosa Klebb, to intercept James Bond while safeguarding their pawn Tatiana Romanova in 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[]

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 after a brutal fight.

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

SMERSH
Auric Goldfinger | Mr. Big | Le Chiffre | Krilencu

SPECTRE
Ernst Stavro Blofeld | Dr. Julius No | R.J. Dent | Three Blind Mice | Miss Taro | Annabel Chung | Rosa Klebb | Tov Kronsteen | Red Grant | Morzeny | Rhoda | Emilio Largo | Fiona Volpe | Count Lippe | Angelo Palazzi | Colonel Jacques Bouvar | Vargas | Ricardo | Mr. Osato | Helga Brandt | Hans | Irma Bunt | Grunther | Braun | Felsen | Josef | Mr. Wint and Mr. Kidd | Bambi and Thumper

Auric Enterprises
Auric Goldfinger | Oddjob | Pussy Galore | Kisch | Mr. Ling | Mr. Solo | Jed Midnight | Jack Strap

Flying Circus
Pussy Galore | Denise | Sydney

San Monique
Dr. Kananga | Tee Hee | Baron Samedi | Adam | Whisper | Dambala | Rosie Carver | Leroy

Hai Fat Industries
Hai Fat | Francisco Scaramanga | Nick Nack | Kra

Stromberg Shipping Line
Karl Stromberg | Jaws | Liparus Captain | Liparus Crew | Naomi | Sandor | Professor Markovitz | Dr. Bechmann

Drax Industries
Hugo Drax | Jaws | Chang

Octopus Cult
Octavia Smythe | Magda | Kamal Khan | Gobinda | Mischka and Grischka | General Orlov

Zorin Industries
Max Zorin | Scarpine | Hans Glaub | May Day | Jenny Flex | Pan Ho | Bob Conley

Sanchez Cartel
Franz Sanchez | Wavekrest Marine Research (Milton Krest & Clive) | Colonel Heller | Dario | Ed Killifer | Joe Butcher | Perez | Braun | Truman-Lodge

Janus Syndicate
Alec Trevelyan | Xenia Onatopp | Arkady Ourumov | Boris Grishenko

Carver Media Group Network
Elliot Carver | Richard Stamper | Henry Gupta | Captain Scott | Stealth Ship Crew | Dr. Kaufman | General Chang | Timblin | Satoshi Isagura | Jeff Hobbs | Philip Jones | Tom Wallace | Beth Davidson | Tamara Steel

King Industries
Elektra King | Renard | Gabor | Sasha Davidov | Mr. Bullion | Giulietta da Vinci | Mikhail Arkov | Trukhin | Lachaise

Graves Corporation
Gustav Graves | Miranda Frost | Tang Lin Zao | Vladmir Popov | Mr. Kil | Dr. Alvarez | General Han | General Li | General Dong | Van Bierk

Quantum/Spectre
Ernst Stavro Blofeld | Mr. White | Le Chiffre | Steven Obanno | Vesper Lynd | Alex Dimitrios | Adolph Gettler | Dryden | Valenka | Kratt | Mollaka Danso | Carlos Nikolic | Leo | Fisher | Dominic Greene | General Medrano | Colonel Carlos | Gregg Beam | Elvis | Lieutenant Orso | Craig Mitchell | Yusef Kabira | Guy Haines | Edmund Slate | Marchetti Pilot | Gregor Karakov | Moishe Soref | Raoul Silva | Patrice | Severine | Boat Captain | Max Denbigh | Mr. Hinx | Marco Sciarra | Moreau | Dr. Vogel | Guerra | Abrika | Marshall | Valerian | Lorenzo | Gallo | Francesco and Marco | Primo

Greene Planet
Dominic Greene | Elvis | Edmund Slate

The Union
Taylor Michael Harris | Le Gérant

Malprave Industries
Adrian Malprave | Nigel Bloch

Phoenix International
Rafael Drake | Kiko Hayashi | Armitage Rook | Ninja

Volotech
Nikolai Diavolo | Katya Nadanova | Arkady Yayakov

Others
Dr. Noah | Capungo | Aris Kristatos | Emile Locque | Erich Kriegler | Hector Gonzales | Claus | Apostis | General Georgi Koskov | Brad Whitaker | Necros | Colonel Feyador | Impostor 00 | Lyutsifer Safin | Valdo Obruchev | Logan Ash | Jack & Seraffimo Spang | Sluggsy & Horror | Mr. Sanguinetti | Anton Murik | Caber | Franco Quesocriado | Nena Bismaquer | Markus Bismaquer | Walter Luxor | Konrad von Glöda | Rivke Ingber | Koyla Mosolov | Tamil Rahani | Jay Autem Holy | Shooter | Steve Quinn | Doktor Kirchtum | Nannie Norrich | Konstantin Chernov | Heather Dare | Norman Murray | Vladimir Scorpius | David Dragonpol | Maxwell Tarn | Felicity Willing | Severan Hydt | Niall Dunne | Mahdi al-Fulan | Nicholas Rathko | Irwin Wolfe | Jean-Paul Scipio | Reade Griffith

Young Bond
Dr. Perseus Friend | Count Ugo Carnifex | Smiler | El Huracán | John Charnage | Colonel Irina Sedova | Ludwig Smith | Wolfgang Smith | Anton Kostler | La Velada | Konstantin Grünner | Andrei Karachan | Adam Elmhirst | Zoltan the Magyar

Never Say Never Again
Ernst Stavro Blofeld | Maximillian Largo | Fatima Blush

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