Caleb relishes adventure – so much so that at nineteen he left home to join a whaleboat crew. He is aware of his environment and quickly able to adapt to it, which increases his odds of survival considerably, but his tendency to leap on an opportunity (ranging from stealing the coat off a corpse and pretending to be someone he isn’t to sneaking behind enemy lines to rescue a friend to making off with hog heads after raiding an enemy camp and setting fire to their storehouse of hay) often places him at great risk. He doesn’t seem to mind; little intimidates him. He is good at paying attention to the environment and adapting accordingly, and is often much more keen than Abe is to get away – Caleb is better at sensing the danger involved in their spy-work and seeing it as essential that all of them make it through the war alive. Caleb is not always great at foreseeing the consequences of his actions, though he does devote himself wholeheartedly to a single pursuit once it is in his sights. His “bad feeling” about rushing into a battle wound up to be a gut hunch that was right on target. Though willing to do bad things for the cause (such as stealing, poaching, shooting the enemy, and undermining the British at every turn), Caleb draws the line at harming innocent people. He actually cares about them, and tries to accommodate for their safety whenever he can. He is remorseful for having done certain things for the cause, and will often step in and refuse to participate in something he does not agree with (he’s angry when people beat up Robert Townsend’s father, rather than simply stealing the cattle and setting fire to the barn – hurting innocent people was not part of the deal). He feels tremendous grief at the thought that he might have given Simcoe the names of his friends under torture, and that sends him into a depressive inward spiral. Sometimes, he and Abe disagree over Abe’s brand of “justice” – Caleb does not always see it necessary to cut through their enemies. Though prone to winging it in general, Caleb also likes to have a firm “plan of action.” He’s able to follow orders, even those he does not particularly like. He will submit to authority, but also tell someone flat out if he thinks they are making a mistake.

Enneagram: 7w6 so/sp

Caleb has a good time wherever he goes. When captured and interrogated by an enemy officer, he ridicules and laughs at the man. He uses risqué or bawdy lyrics to connect to his agents in the field, and employs a sense of humor when trading banter with them (a man insults him by remarking on all the women Caleb has been with; he quips back that’s not a nice thing to say about your own ma! And waits for the man to laugh). He throws around wit in the trenches, on the river, and in the battlefield, in an attempt to keep things light, and often tries to diffuse others’ tensions by being funny. He asks if he can tease Anna and Ben Talmadge about being thought of as lovers later (no!!). His 6 wing is aware of danger and doesn’t want to be caught. Caleb is much more in favor of whisking any friends in danger away to safety than he is standing and fighting. He also likes to recruit small batches of people, since he feels more of a sense of safety in numbers. He’s aware of his own mortality and does not take unnecessary risks.