Dick checks into a New York hotel, hopeful that Grandison will visit with the free Black men employed by the hotel, who will “inoculate” Grandison with the “virus of freedom.” Dick can’t risk actively encouraging Grandison to take his chance at freedom, but he can give him “sufficient latitude” to take it.

For two weeks, Dick enjoys mingling with fashionable young people. He gives Grandison pocket money and expects to find the man gone some night. But Grandison doesn’t leave. When Dick asks why, Grandison says he’s talked to the free Black men but doesn’t care for them. They think they’re better off, but he knows they’d be happier in a Southern state.

Dick and Grandison travel to Boston, where Dick hopes he’ll have better luck nudging Grandison toward freedom. Dick writes anonymously to several abolitionists that a “wicked slaveholder” has brought a slave to the “liberty-loving” city, asking, “Shall this be tolerated?” He sends Grandison on errands that put him in the way of the letter’s recipients. Once he sees a man talking with Grandison. On another day, he happens upon Grandison speaking with a preacher. But when Dick approaches, Grandison hurries to him, complaining that abolitionists keep bothering him. He says he’ll be glad to get home.

The next day Dick tells Grandison that he’s going away for a few days. He leaves cash for Grandison to use to “enjoy your liberty while you may.” When he returns, Grandison has not touched the cash. Perplexed and irritated, Dick writes to his father to commend Grandison. The colonel tells friends that if Boston newspapers interviewed Grandison, they’d report how happy slaves in the South are. Dick also writes to Charity, assuring her that he’s trying to achieve “something serious.”

Dick decides to take Grandison to Niagara Falls to get him into Canada. As they view the Falls one morning from the Canadian side, Dick explains that Grandison can simply walk away, free. Grandison nervously asks to return to the States. Dick then tells Grandison to wait while he walks to a nearby inn. From the inn, he watches till he no longer sees Grandison. Walking hopefully to the Falls, Dick finds Grandison napping in the sun.

He returns to the inn, where a waitress sees Dick talk to the inn’s stableman, give the man something, and then leave. She also sees two young men hurry to the Falls.