A fearsome sailor with a scar on his cheek takes up residence at the Admiral Benbow Inn, owned by Jim's parents. The sailor avoids company, and Jim soon understands that he is afraid of someone. One day, the sailor takes him aside and says he will give him a four-penny a month to be on the look out for a one-legged seafaring man. If he does show up, Jim is to tell the scar-faced sailor right away.
This mysterious one-legged seafaring man haunts Jim's dreams as a fearsome creature. Jim imagines him in all sorts of different guises, such as with his leg cut off at the knee or at the hip or as having only one leg in the middle of his body.
Therefore, when the squire gives him the note to bring to the one-legged sailor Long John Silver, on the surface Jim, is delighted with the task, but underneath, he is apprehensive. He fears this one-legged man might be the one whom he has been put on the lookout for and has built up in his mind as a monster. Jim narrates,
Now, to tell you the truth, from the very first mention of Long John in Squire Trelawney’s letter I had taken a fear in my mind that he might prove to be the very one-legged sailor whom I had watched for so long at the old Benbow.
Jim is, therefore, very relieved when he sees the one-legged Long John Silver looking friendly and behaving like a normal, cheerful person.