Long John Silver
We think Long John Silver is the best part of this book. He's totally what we imagine a pirate should be: cunning, sly, peg-legged, with a parrot on his shoulder. There's a reason why he's what we think of when we hear the word "pirate." It's in part because of Long John Silver's popularity as a character that Treasure Island has become the most popular, most enduring pirate novel ever. Long John Silver seems like the classic pirate because he's the character whom all other pirates in popular culture are based on. He's the granddaddy of them all, and we love him for it.
Long John Silver is a quartermaster, which means he handles the ship's food and drink during the voyage. That's also why his fellow pirates call him Barbecue. He's apparently the only man whom the legendary pirate Captain Flint was afraid of ("Flint his own self was feared of me" (11.13)). And since we discover later in the book that Captain Flint managed to singlehandedly kill six of his crew while he was burying his treasure on the island, Long John Silver must be a pretty tough, terrifying guy. But he's first and foremost a con man, so the rage and violence that lie under the surface are hidden underneath a mask that's as smooth as pudding.
We see examples over and over again of Long John Silver's incredibly persuasive manner. He tricks Squire Trelawney, who is, OK, not that bright. Still, the fact that a man as interested in duty and class as Squire Trelawney would believe a quartermaster (Long John Silver) over a captain (Captain Smollett) is a sign of how persuasive Long John Silver can be. We also get to watch him convincing young Dick Johnson to join the pirates while aboard the Hispaniola:
You may imagine how I felt when I heard this abominable old rogue [Silver] addressing another in the very same words of flattery as he had used to myself. I think, if I had been able, that I would have killed him through the barrel. (11.6)
What irks Jim the most about Long John Silver's show of friendliness and respect for Dick Johnson is that he recognizes that Long John Silver has been using the same lines on Jim himself! Jim may be creative and intelligent, but he's no match for the slippery Long John Silver.
The thing is, Long John Silver has a lot of qualities that make him appealing to the reader: he's incredibly wily and well-spoken, he's practical and quick to change sides if he needs to, and he's brave. Actually, if you just read the descriptions without thinking "pirate," Long John Silver sounds a lot like an older, smarter version of Jim Hawkins. But of course, he is a pirate (or "gentleman of fortune," as he likes to be called), so he can't totally win out in the end. Even Stevenson, who is pretty unconventional, can't allow Silver to succeed in his original plan of killing all the non-pirates on board the Hispaniola and making off with all 700 thousand British pounds of treasure.
Still, the fact that Long John Silver is so appealing means that it would be equally unsatisfying to the reader for him to be shot down like a dog (like Israel Hands) or marooned on the island (like Tom Morgan). We like him, even if he is a rogue. So the book compromises by letting Long John Silver disappear: he slips away from the Hispaniola with a sack of coins when Squire Trelawney, Doctor Livesey, and Jim Hawkins are ashore at the end of the novel. Long John Silver may not get exactly what he wants, but he escapes punishment, as all good tricksters should.
Long John Silver's inconclusive ending also leaves open the possibility of future adventures. Who knows where or when this charming, cunning pirate might show up again? After all, there are still bars of silver buried on Captain Flint's island. Treasure Island's open-endedness invites the reader to imagine future adventures using the colorful character of Long John Silver as a stand-in. By leaving a question mark over his fate, we can dream of meeting him ourselves – and perhaps getting caught up in treasure hunts of our own.
Long John Silver is unlike all the other pirates in this novel in two ways: he owns property and he has a wife. (Three if you count the fact that he's smart, and most of the others are total idiots.) Long John Silver is the legitimate owner of a pub in the coastal town of Bristol, and he's married to an African woman. (Stevenson calls this woman a derogatory term for a black woman; we won't reproduce it here because we find it offensive.) Neither of these facts takes up a huge amount of space in the novel, but they indicate something special about Long John Silver: he blurs boundaries.
Where the other pirates of the novel drink their fortunes away and go back to begging or crime all too quickly, Long John Silver is planning for the future. He's settling down and trying to become an actual gentleman, not just a gentleman of fortune. Even Israel Hands comments:
He's no common man, Barbecue, [...] He had good schooling in his young days, and can speak like a book when so minded. (10.14)
The fact that Long John Silver is an educated property owner not only differentiates him from the other (wasteful, reckless) pirates of the novel. It also suggests untold adventures in his past. What brought an educated man to piracy? How did he get to be sea-cook to Captain Flint? Long John's Silver's intriguingly unclear origins lend a sense of mystery and excitement to the character.
For readers of Robert Louis Stevenson's day, Long John Silver's mixed-race marriage would have been a part of that mystery. He is married to an African woman at a time when mixed-race marriages were not common or even considered acceptable. So he lives both inside and outside the law. He owns property (inside the law), but is still a pirate (definitely outside the law). And he is married (inside the law), but to a woman of a different race (socially unacceptable in the 19th century). He breaks rules and challenges the simplistic binaries of good guy/bad guy in multiple ways, which makes him all the more alluring.
The Real Life Long John
The character of Long John Silver is based on a real-life buddy of Robert Louis Stevenson's (sadly, not a real-life pirate): William Ernest Henley. Like Stevenson, Henley was a writer of renown. Also like Stevenson, Henley spent much of his life sick with tuberculosis. He even had to have his leg amputated (hence Long John Silver's peg-leg). But Henley never let his illness stop him from participating actively in the literary scene of 19th-century Britain. His stubbornness, courage, and intimidation of lesser minds around him made him a compelling figure, and an excellent model for gentleman pirate Long John Silver. (Read more about Henley here.)