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Dr. Livesey is The Doctor Himself
Well, if he was Merlin, this can't be too far a stretch.
  • Dr. Livesey shoots people, so it can't be.

Long John Silver's pirates are secretly Patriots agents traveled back in time
They sent back in time to Captain flint's treasure, and the Patriots ordered them to kill John Silver if he helped out Captain Smollet

Alternatley, Long John Silver's pirates are secretly collaborated with the The East India Trading Co.

Long John Silver eventually invested his share of the treasure to open a seafood restaurant

Obviously, it became huge later on. You may have even eaten there.

  • Heck, this is what he was doing when he's introduced.

Long John Silver is Jim Hawkins's biological father.
Hawkins is the only child of a man and his wife who live in a remote tavern some distance from even the nearest village. The father is sickly and dies early in the story, just after Billy Bones's first stroke. It is likely that he was not virile enough to father more children despite all the dull winter evenings he and Mrs Hawkins must have had to pass, and what is more likely than that he was not virile enough to father Jim either? Meanwhile, thirteen or fourteen years previously, John Silver was not a crippled ex-pirate of fifty, but a well-off plausible rascal of thirty-odd, and could perfectly well have caught the eye of a neglected wife in a remote tavern. Hawkins senior, of course, would have kept quiet about any doubts about Jim's parentage, lest he become a laughing-stock. This explains well why Silver liked Jim from the start and was willing to defy the whole pirate crew rather than let Jim be put to death, and why he trusted Jim not to run away with the doctor, and why he backed Jim to side with him in the final confrontation with the pirates.

Israel Hands Is Captain Hook
This might sound ridiculous, but in the original Peter Pan, Hook is described as having been "Blackbeard's boat swain", and "the only person Barbecue feared". Barbecue is one of Long John Silver's names, and the only survivor of Blackbeards crew was a man named Israel Hands who testified against the other pirates in return for clemency. While it's generally assumed Hands died in poverty in London, it's never been confirmed, and it would explain why Hook refused to speak of his original identity.

Admiral Benbow was a cover for smugglers
An inn in the middle of nowhere, where nobody stays and few visit the bar. When the owner gets a single guest, he is unhappy and complains. Yet he somehow has a stable income. The answer — the inn is a cover for something profitable. Probably, smuggling, since the sea is near.
  • While, given the era, it's not out of the realms of the impossible that his tavern has at least some dodgy dealings going on, Jim's father is unhappy and complains about his guest because said guest is disruptive, abusive, violent-tempered and doesn't actually pay his bills.

Doctor Livesey isn't a medic
  • He seems to be better at killing than healing.
  • His onscreen patients tend to die. The exception was left in other people's care.
  • Considering when this is set, many landlords fled abroad from the king, leaving their estates to various managers. Livesey may have been inspecting them and collecting money for the owners.
  • Trelony may have been one such manager.

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