Chapter 8: At the Sign of the Spy-glass
The next morning, Squire Trelawney sends Jim out to deliver a message to John Silver, who operates his own little tavern called the Spy-glass. And it seems like Silver isn’t too bad off despite the lack of pension, because the establishment is clean and well-kept, and the place has a lively spirit.
This extends to Silver himself; when Jim lays eyes on him for the first time, he’s effortlessly moving through the cramped space despite his reliance on a crutch, and he’s cheerfully chatting and laughing with his patrons. Jim assures us that when Trelawney’s letter last chapter mentioned that Silver only had one leg, he immediately called “sus”; but thinking back to the visit of Black Dog—who was a terrible man with a terrible name—and comparing him to Long John Silver—who is a cool man with a cool name—he decides in this moment that Silver would never associate himself with that kind of villainy and can’t possibly be the same guy the captain warned him about.
As he introduces himself to John Silver and hands him Trelawney’s note, Jim’s attention is drawn to a man in the corner of the tavern who suddenly gets up and tries to slip out the front door unseen. Unfortunately for the man, Jim recognizes him. And speak of the devil—it’s Black Dog himself!

John Silver
Jim alerts Silver, who says he must be running out on his tab, and orders some of the other patrons to go chase after him and bring him back. But then he goes, oh, Jim, you know that guy? Jim says, yeah! Didn’t Trelawney tell you about the pirates? He was one of them!
Silver immediately starts to chew out the guy who was drinking with Black Dog, who claims he didn’t know the man and tries to play dumb when Silver asks what they’d been talking about, until the drinking buddy unhelpfully responds with “sailing stuff”. Silver lets him go, then starts berating Black Dog as a scoundrel for a while, until he realizes that on top of everything else, Black Dog actually didn’t pay his tab. Then he starts laughing at himself for not remembering sooner, exclaiming “shiver my timbers!” because that hasn’t become a pirate cliché yet.
Once again, you might be losing it now, shaking your screen and going “You’re telling me that Black Dog was hanging out in the one-legged man’s bar and that’s somehow NOT SUSPICIOUS???” To which, Jim tells us, yep, that definitely put him on his guard again. But then he does something different: he admits that Silver out-foxed him here, and tells us that, in that moment—as Silver was cussing out Black Dog and reading the riot act to the patrons who ultimately came back empty-handed—Jim would have voted Long John Silver for president. One could infer from his phrasing that this is a stance he no longer holds.
For now, though, Silver accompanies Jim back to where Trelawney is staying following the docks along the way. As they walk, Silver tells him stories about the ships and teaches him some nautical phrases, and Jim finds himself quite pleased with Long John’s company.
When they reach Squire Trelawney, Dr. Livesey is now with him. Silver describes the encounter with Black Dog in great detail, then departs. Livesey remarks, “Trelawney, you’re useless most of the time, but I reckon you did good finding this Long John fellow.”