“My heart was sore for him, wicked as he was, to think on the dark perils that environed and the shameful gibbet that awaited him.” (Stevenson 129)
Jim Hawkins sees that Long John Silver is playing a risky game, trying to please and pacify his pirate gang while looking for a way to make peace with Jim's friends and save his own life. Knowing the dangers of this decision, Jim feels sorry for silver, especially since he lost his life because his life will likely end with death by the way things are getting handled. What Jim know about Silver and his bad decisions and murderous ways he looks past that due to the way he feels about Silver. There's a likeable side to the man that Jim cannot ignore and which stirs feelings of pity.