After the trial, the happy group goes to eat at the Afric Queen, where many of the Whigs stop by to congratulate Josiah Quincy for humiliating Merchant Lyte. Johnny finds out from Rab how he got Cilla to come--all he had to do was present Mrs. Lapham with a fake court letter stating an order from the governor (Mrs. Lapham's is illiterate).
Too proud to lodge with Rab or at the Lapham household, Johnny decides to get a job as a cabin boy. But as he has no money to buy the necessary things to set sail, he heads over to Merchant Lyte to sell his silver cup. There, Merchant Lyte steals the cup from him and makes it look as if Johnny meant to return the cup. When Merchant Lyte calls on one of his henchman, Johnny runs away. He runs to the office of the Boston Observer where he sees Mr. Lorne. Johnny asks if he can take the job as a rider, even though he has never been on a horse before. Rab agrees to teach him. For his job, Johnny is to deliver the Boston Observer all over the Boston area from Thursday to Saturday. And to Johnny's delight, Rab even suggests that he share the attic with him.
Rab explains that the horse, Goblin, is difficult to ride because it is unusually scared of everything. Johnny gets one lesson and is then left to learn by himself. As with all things, Johnny catches on quickly, and he is soon delivering the Boston Observer with Goblin. Moreover, Johnny enjoys riding down the country roads, making grand entrances into town in a full gallop, and talking politics with news-hungry townspeople. Johnny goes from knowing almost nothing about politics to a well-informed, knowledgeable Whig.
Johnny discovers that the attic he shares with Rab is a secret meeting place of the Boston Observers, a secret club of powerful Whigs who meet to discuss political strategy. Johnny adjusts quickly to his new life as a rider. Mr. and Mrs. Lorne treat him well. He even has four days a week to do his own stuff, like make extra money delivering letters for guests at the Afric Queen. He spends most of his free time, however, reading from Mr. Lorne's library. Unlike Mrs. Lapham, Mrs. Lorne never bothers Johnny when he is idly reading. Sometimes Johnny is asked to take care of the Lorne baby who is, like Rab, "a regular Silsbee of Lexington." Although he tries not to show his love for the baby in front of Mrs. Lorne, she knows, and thus shows much kindness to the motherless, orphan Johnny.
After a couple of weeks delivering papers, Johnny runs into Cilla and Isannah at the town pump in North Square. He finds out that Cilla is now doing the work of fetching water, a chore previously done by the boys. Johnny helps Cilla carry the buckets of water and asks if they can meet every Thursday and Sunday. Cilla says maybe. Johnny realizes how much he misses being around Cilla and Isannah.
The more time Johnny spends with Rab, the more he learns about himself. Rab is so unflappable and consistent; Johnny is easily influenced by circumstance. So when Rab confronts Johnny about why he is so quick to put people down, Johnny decides to think before he does and says things. This comes in handy when a black servant girl of Sam Adams accidentally throws dishwater on Johnny when he is riding by. Instead of cursing her, as he would have normally done, he counts to ten. She apologizes and invites him into the house, where he meets Sam Adams. Johnny begins doing delivery jobs for the great Sam Adams.
That fall, Johnny twice sees Rab out of his usual cool character. Once, in Lexington at Rab's grandfather, Major Silsbee's barn dance, Johnny sees Rab thoroughly enjoy himself. After the dance, Johnny notices that he had not thought about his lame hand and neither had the girls he danced with. Rab tells Johnny that if he forgets about his hand, people will forget as well, but if he treats his hand like a horrible disfigurement, others will pick up on that. Another time, the Webb twins get bullied by the butcher's boy at the butcher shop. Hearing their cries, Rab and Johnny go over to take on the butcher's whole family. After the fight, Rab hardly mentions it. Johnny is amazed that someone who can fight so well never really gets into fights, and moreover, never boasts about it. Johnny learns from Mrs. Lorne that all Silsbee men are like that--they never let anyone know what they are thinking or feeling.
