Caleb BrewsterPlayed by Daniel Henshall
A vital member of the Culper Ring, Caleb acts as a courier, constantly putting himself at risk by relaying messages between Abe and Ben. Though very little intimidates him, Caleb was shaken to his core last season when Captain Simcoe executed his uncle right in front of him during the Battle of Setauket. Normally a man who relishes action, Caleb had advised Ben to wait before rushing headlong into battle and now harbors resentment towards him for his rash decision. Vowing revenge on Simcoe, he buries the rage he feels towards Ben, but his anger can only be held down for so long.