In Treasure Island, Long John Silver is a pirate who was quartermaster under the notorious Captain Flint. Long John Silver had a pet parrot called Captain Flint, often seen sitting on his shoulder where she would nibble on seeds. A quartermaster on a pirate ship ranked higher than any officer except the captain himself, and could veto the captain's decisions whenever the ship was not in a battle. The quartermaster was elected by the crew and one of his tasks was to lead the boarding party from the quarterdeck during boarding attacks. Silver claims to have served in the Royal Navy and lost his leg under "the immortal Hawke". "His left leg was cut off close by the hip, and under the left shoulder he carried a crutch, which he managed with wonderful dexterity, hopping about upon it like a bird. He was very tall and strong, with a face as big as a ham – plain and pale, but intelligent and smiling." He claims to have been the only man whom Flint ever feared. Like many of Stevenson's characters, there is more than a modicum of duality in the character; ostensibly Silver is a hardworking and likeable seaman, and it is only as the plot unfolds that his villainous nature is gradually revealed. His relationship with Jim Hawkins, the novel's protagonist, is interesting, as he serves as a mentor and eventually father-figure to Jim, creating much shock and emotion when it is discovered that he is in charge of the mutiny, and especially when Jim must confront and fight him later on. Although willing to change sides at any time in the interests of his own survival, Silver has compensating virtues: he is wise enough to pay attention to money management, in contrast to the spendthrift ways of most pirates, and is physically courageous despite his disability; for instance, when Flint's cache is found to be empty, he coolly stands his ground against five grown men despite having only Hawkins to back him.
Historians have noted that Silver's account of his life experiences during the first half of the 18th century is at variance with the known history of the historical figures he mentions, and that Silver is either exaggerating the range and scope of his exploits for the benefit of Jim Hawkins or for potential pirates he is trying to recruit, or his memory is faulty.
When Silver escapes at the end of the novel, he takes "three or four hundred guineas" of the treasure with him, thus becoming one of only two former members of Captain Flint's crew to get his hands on a portion of the recovered treasure; a separate cache of bar silver is apparently left on the island. (The repentant maroonee Ben Gunn is the other, but he spends all 1,000 pounds in nineteen days.) Jim's own ambivalence towards Silver is reflected in the last chapter, when he speculates that the old pirate must have settled down in comfortable retirement: "It is to be hoped so, I suppose, for his chances of comfort in another world are very small."Stevenson's portrayal of Silver has greatly influenced the modern iconography of the pirate. Silver has a parrot, named Captain Flint in mockery of his former captain, who generally perches on Silver's shoulder, and is known to chatter pirate phrases like "Pieces of Eight," and "Stand by to go about." Silver uses the parrot as another means of gaining Jim's trust, by telling the boy all manner of exciting stories (many of them likely fake) about the parrot's buccaneer history. "'Now that bird,' Silver would say, 'is, may be, two hundred years old, Hawkins- they live forever mostly, and if anybody's seen more wickedness it must be the devil himself. She's sailed with England- the great Cap'n England, the pirate. She's been at Madagascar, and at Malabar, and Surinam, and Providence, and Portobello ... She was at the boarding of the Viceroy of the Indies out of Goa, she was, and to look at her you would think she was a babby."
He is married to a woman of African descent, whom he trusts to manage his business affairs in his absence and to liquidate his Bristol assets when his actions make it impossible for him to go home. He confides in his fellow pirates, that he and his wife plan to rendezvous after the voyage to Skeleton Island is complete and Flint's treasure is recovered, at which point Silver will retire to a life of luxury.
According to Stevenson's letters, the idea for the character of Long John Silver was inspired by his real-life friend William Henley, a writer and editor. Stevenson's stepson, Lloyd Osbourne, described Henley as "...a great, glowing, massive-shouldered fellow with a big red beard and a crutch; jovial, astoundingly clever, and with a laugh that rolled like music; he had an unimaginable fire and vitality; he swept one off one's feet". In a letter to Henley after the publication of Treasure Island Stevenson wrote: "I will now make a confession. It was the sight of your maimed strength and masterfulness that begot Long John Silver...the idea of the maimed man, ruling and dreaded by the sound, was entirely taken from you".