“Well, squire … I don’t put much faith in your discoveries, as a general thing; but I will say this, John Silver suits me.”

Dr. Livesey delivers these remarks to Squire Trelawney at the end of Chapter VIII, when the men first meet the crew that will accompany them to Treasure Island. This quotation raises the issue of judgment of another person’s character. First, Livesey’s skepticism about Trelawney’s prudence suggests that the squire’s knowledge of human affairs might be less reliable than that of the practical man of science. We later verify this hypothesis when we discover that the squire has been tricked into manning his ship with a band of pirates; his judgment is indeed unsound. Yet Long John Silver tricks even the wise Dr. Livesey. Though in reality the ringleader of the pirates, Silver is a man whom Livesey trusts instinctively. The doctor’s trust suggests that Silver has extraordinary powers of deception, but also that there is something genuinely likable about the pirate. Even though Silver is a miscreant, he is charismatic and repeatedly earns the respect of others. Indeed, Silver wins Jim’s affection and admiration by the end of the adventure, and he acts like a gentleman on several occasions. Livesey and Trelawney are deceived by Silver because he is such a contradictory character, not fully good but not fully evil either.