Wilkes looks up a school friend, Michael O'Laughlen. He asks O'Laughlen to hook him up with Rebels in Maryland. O'Laughlen tells him that the attempt on Lincoln's life has failed and that Maryland is under Federal martial law and is not going to secede. Then he introduces Wilkes to shoemaker Christian Emmerich and Marshal George Kane. Kane is defecting to the South. At Kane's request, Wilkes agrees, rather than join a fighting unit, to stay in the North and help in the smuggling of contraband such as medicines across the lines to the South. Atfer Bull Run, Emmerich sends Wilkes to Philadelphia to pick up a package. Wilkes stays with Asia and tells her what he's doing. She is thrilled.