Caleb Brewster is captured by the Brits and taken into custody. General Washington worries that he will expose the Ring.

Caleb's childhood friend and fellow Culper Ring member Major Tallmadge wants to stage a rescue operation, but Abe thinks he has a better idea. He suggests they make a trade instead. The judge agrees, but only if he can be used in the prisoner exchange. Abe agrees that they will do it together.

Benedict Arnold gets nowhere questioning Caleb, so he leaves the interrogation up to Col. Simcoe. He proceeds to torture Caleb by cutting him with his sword and then burning him. Caleb still doesn't talk and even spits in his face at one point. Simcoe thinks that he has discovered who is truly in the Culper Ring and tries to get Caleb to confess.

He looks forward to the prisoner exchange so he can prove the Woodhulls are working against the crown.

We learn Simcoe's backstory: He had a rough childhood and has never stepped foot in England.

Anna continues to carve out a role for herself in Washington's camp. She opened a trading post and has started to advocate for the other women outside the camp. But she wants to be part of the Ring.