Donald “Red” Grant

Donald “Red” Grant – Setting the Bar High for Future Henchmen

Meet Donald “Red” Grant, or simply Red Grant, a cold-blooded assassin in the employ of the shadowy criminal syndicate, SPECTRE. As the notorious henchman in the 1963 James Bond film, From Russia with Love, Grant was brilliantly portrayed by the late British actor Robert Shaw.

The character, originally named Donovan Grant, first appeared in Ian Fleming’s 1957 novel, where he was a ruthless killer with a penchant for violence. When he made the leap to the big screen, a few subtle changes transformed him into the iconic figure we know today.

Standing shoulder to shoulder with the likes of Rosa Klebb, Oddjob and Jaws, Red Grant has etched his name into the annals of Bond history as one of 007’s most iconic henchmen. His relentless brutality, cunning intellect, and unwavering loyalty to SPECTRE set the bar for the many henchmen who would follow in his lethal footsteps.


His striking features and piercing gaze made him the perfect antagonist to face off against Sean Connery’s suave and debonair James Bond, played by Sean Connery. The battle of wits and strength between the two created some of the most memorable moments in the Bond franchise.

As a character, Red Grant’s chilling efficiency and cold-blooded nature have made him a fan favorite, and his legacy lives on in the Bond universe. His impact on the franchise is undeniable, as his archetype has been replicated and adapted over the years, proving that the chilling presence of Red Grant still looms large over the world of James Bond.

Rosa Klebb tests Red Grant out with a knuckle duster

Donald “Red” Grant

Having been imprisoned for murder, Red Grant proved he was a force to be reckoned with when he escaped Dartmoor Prison in 1960. Just two years later, SPECTRE recognized his potential and recruited him as an elite agent and assassin. With his exceptional combat skills and ruthless nature, Grant quickly became a valuable asset to the criminal organization.

While Red Grant has been training under Morzeny’s watchful eye, SPECTRE has been hatching a plan to obtain a Soviet Lektor decoding machine by manipulating both Soviet and British intelligence. Enter Tatiana Romanova, a supposed Soviet defector, who is to deliver the Lektor to MI6 agent James Bond aboard the Orient Express.

Grant, the star of SPECTRE, is handpicked by Colonel Rosa Klebb, under orders from SPECTRE leader, Ernst Stavro Blofeld, to eliminate Bond and Romanova and snatch the precious Lektor.

After proving himself to Klebb, who punches him in the stomach wearing a knuckle duster, Grant sets off for Istanbul to await further instructions. Upon his arrival, he ensures Bond’s safety by eliminating enemy agents and thwarting assassination attempts.

In Istabul, Red Grant flexes his deadly skills by overpowering and killing a Russian agent tailing 007. He strategically leaves the body outside the Soviet embassy to frame Bond, igniting tension between Britain and the Soviet Union.

Recognizing Bond’s survival as crucial to SPECTRE’s plans, Red Grant stays close, covertly providing protection by killing a Soviet assailant led by Krilencu in a camp of militant Roma. The following day, the SPECTRE henchman continues his secret guardian angel act, discreetly taking out another enemy agent tracking Bond at the Hagia Sophia.

Donald "Red" Grant

Bond and Tatiana have now managed to steal the Lektor and get it onto the Orient Express headed for Western Europe, but Red Grant expected this and tracked them. On the train, Red Grant kills Bond’s MI6 ally Ali Kerim Bey and a Soviet agent, making it look like they’d killed each other.

Then Red Grant adopts the persona of a fellow British agent, Captain Norman Nash, whom he had killed during a train stop in Zagreb and Bond is supposed to meet. This guise allows Grant to gain Bond’s trust.

As they dine together on the train, Red Grant discreetly drugs Tatiana by lacing her wine with chloral hydrate. Once they assist the incapacitated Romanova back to Bond’s carriage compartment, Grant strikes, rendering Bond temporarily unconscious with a swift blow to the head and disarming him.

With Bond at his mercy, Grant unveils his true identity and scheme, presenting an 8mm film of Bond and Romanova’s intimate moments in his Istanbul hotel. To twist the knife further, he also produces a forged letter, purportedly penned by Tatiana, threatening to leak the film to the media unless Bond agrees to marry her.

In an attempt to buy time, Bond tricks Red Grant into opening an attaché case rigged with tear gas, sparking a vicious battle between the two. Grant tries to strangle Bond using the garrote wire hidden within his wristwatch.

Bond turns to his trusty Q Branch attaché case, revealing a concealed, flat-bladed throwing knife. He plunges the weapon into Grant’s left arm before turning the tables, using Grant’s own garrote to strangle him.

How Donald “Red” Grant Differs in the novel

While both the book and film versions of Red Grant portray him as a chilling and seemingly unstoppable killer, there are a few notable differences in the character’s motivations and backstory.

In Ian Fleming’s novel, Red Grant is depicted as a highly eccentric individual, with a unique set of quirks that make him even more unnerving. One such peculiarity is his compulsion to commit murder during the full moon, an urge that resembles a werewolf’s transformation. This lunar-driven bloodlust adds an extra layer of mystique to the literary version of Grant, making him an even more intriguing and terrifying character.

Also, in the novel Red Grant doesn’t kill Captain Norman Nash, and this character doesn’t exist, although Bond is unaware that no agent was sent.

Donald Red Grant holding Bond at gunpoint

Actor Robert Shaw

The actor that played Red Grant, Robert Archibald Shaw was born in 1927 in Lancashire, England. Both his parents were medical professionals, but Shaw would ultimately follow a different path. He attended school in Lancashire until the age of 12 when, following his father’s death, his family relocated to Cornwall.

Excelling in physical activities at Truro, Shaw eventually found his way to the Royal Academy of Dramatic Arts in London, supported by a £1,000 inheritance.

Robert Shaw made his stage debut in 1949 and quickly found success at the Old Vic, playing memorable roles such as Cassio in Othello and Lysander in A Midsummer Night’s Dream. By 1952, he had earned prestigious West End roles, starting with Caro William. Around this time, he also began appearing in television and film, marrying his Old Vic co-star Jennifer Bourke.

The actor landed a cameo in The Lavender Hill Mob before making an impression as Pulford in The Dam Busters (1955). Soon after, he starred as a pirate-turned-privateer in the series The Buccaneers (1956), which ran for 37 episodes. More film and TV roles followed, including a part in the spy-fi series Danger Man.

Robert Shaw’s international career really took off when he was cast as Donald “Red” Grant in From Russia with Love. Unfortunately, the same year also marked the end of his marriage to Bourke, with whom he had four children.

Despite his growing film career, Shaw also pursued writing. His first novel, The Hiding Place, was published in 1960, followed by the Hawthornden Prize-winning The Sun Doctor in 1962. He even ventured into journalism, covering the Rome Olympics as a reporter.

Many consider Shaw’s career to have peaked with his role as the eccentric shark-hunter Sam Quint in Steven Spielberg’s Jaws (1975). And he later reunited with Sean Connery in Robin and Marion (1976). Other appearances in Swashbuckler (1976), Black Sunday (1977), The Deep (1977), and Force 10 from Navarone (1978).

Tragically, while filming Avalanche Express, Shaw suffered a heart attack and passed away on August 28, 1978, in Tourmakeady, County Mayo, Ireland.

Donald “Red” Grant

More than 60 years on, Donald “Red” Grant remains an enduring and chilling figure in the world of James Bond villains. His ruthlessness, cunning, and sheer physical prowess set a benchmark for the henchmen who followed in the 007 franchise.

Whether on the pages of Ian Fleming’s novel or portrayed by the talented Robert Shaw on the big screen, Red Grant’s cold-blooded efficiency and calculating nature continue to captivate and terrify audiences.

As one of Bond’s most iconic adversaries, Red Grant’s legacy lives on, he’s regularly brought back in video games, and other villains who portray similar characteristics as him, reminding us of the relentless and formidable man that was Donald “Red” Grant.