Benjamin has a group-focus, seeing the Culper ring as just that, a group in which his personal involvement is necessary and whose identities he intends to protect with his life. He is an avid recruiter, able to convince several individuals to join their ranks, and all without undue pressure, influence, or more than the passion and power of his words. He quickly picks up the emotional connections between others, sensing through them that he cannot trust them – such as connecting Major Andre’s wistful statement that he did it “all for a woman” to seeing Peggy Shippen weeping at his execution, and knowing they had a romantic connection, which would make her a spy. Benjamin is so empathetic to people, he orders her to escape to her husband’s side as quickly as she can, to avoid detection and being tried as a conspirator. He tries to convince another woman with whom he had a brief fling to lie about her loyalty to the British and change sides, to save her life (his Fe belief that morals ought to be based on survival and socially acceptable lies). He rallies people around him through public speeches. But his inferior Ti shows up, when Sackett is appalled by his “lack of safety” in dealing with the Culper ring. Benjamin never thought about protecting their identities until introduced to the idea; he doesn’t want to cut Woodhull out of the ring, when Washington sees the messages as taking too long to arrive (because it will hurt Woodhull’s feelings). As such, he makes all his decisions based on emotion, including his loyalty to Washington. He notices things and pays attention to details that others miss, such as Peggy’s connection to Major Andre – he recognized her based off a little sketch of her eyes in the major’s journal. Just her eyes. Nothing else. Benjamin is meticulous in how he sets up the Culper ring, and since it works, does not rethink it, until Washington draws his attention to matters of ‘expediency.’ Washington also challenges him several times on making decisions purely in the moment – because Benjamin did not stop to think about the potential far-reaching consequences of something (such as keeping Arnold’s letter from the general for 24 hours, or not protecting the ring through various hand-offs, rather than having one spy give another the information directly). Much of his decisions and biases come from his college days, his friendships there, and his sentimental fondness for his recently deceased friend, Nathan Hale. But Benjamin also has quite good intuition at times. He suspects on minimal evidence that they cannot trust Benedict Arnold, despite all indications otherwise (and his long personal friendship with Washington) – leading to them discovering his treason, when he happens to recognize Andre carrying a fake pass. He sees people’s potential as spies and sometimes feels frustrated with Washington’s decisions, since they do not fit how he sees the situation.

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Benjamin over-extends himself, in his desire to help others – from the woman in the woods who gave him shelter and then saved his life when the British came knocking, but then who ‘turned traitor’ and tried to do the Patriots harm, to his friend and idol, General Washington. He can be a bit too eager to offer his assistance, but it is invaluable nonetheless. Benjamin is often appalled at their barbaric methods, and tries to soften them where he can, and to do ‘good’ within the camp. He is also deeply principled, not always approving of Abe’s methods, Caleb’s stealing, or Washington’s logical, emotionless tactical decisions. Benjamin lives a principled life as much as he can, and tries to atone for his mistakes.