The Horseman of War on Sleepy Hollow is a lawyer. Or pretending to be one. Either way, just lovely for our reputation as attorneys.

The reveal came at the end of The Kindred when Henry visited former Sheriff Frank Irving in a prison psychiatric hospital. The NEW Sheriff in town apparently was pushing the limits on cruel and unusual punishment, seeking not just psych evaluations, but threats of electric shock therapy. “Henry the Lawyer” appeared to put a stop to the tests, which is what a lawyer is exactly supposed to do for his client at object police torture.

However, Henry had Irving sign papers (most likely the engagement letter) that pricked the former sheriff’s finger, in effect making him sign the engagement letter in blood.

This raises many important legal issues. No one should EVER sign a contract of any type without reading it first. God knows what evil clause is in there that could negatively impact Frank Irving. No legal fees or retainer could include someone’s soul, even though not specifically stated in any state’s ethical rules.

Henry might be a powerful warlock, but that does not mean he passed the bar in the late 18th Century. New York does not permit people to engage in the unauthorized practice of law, warlock or not. The law specifically prohibits any “natural” person from holding themselves out to the public to practice law (including appearing in Court and advertising), without having been licensed, admitted to practice law in New York, and taken an oath to the Constitution. NY CLS Jud § 478.

If Henry is a licensed attorney, he has several major breaches of his ethical duties. The first being having his client sign a blood oath that likely goes against his client’s interests. This act would violate his Duty of Loyalty to Frank Irving to not act adversely against his client.

Henry also has a significant conflict of interest with Irving, as Henry’s goal is to bring about the Apocalypse under the direction of Moloch, which goes against Irving’s interests.  A lawyer may not represent someone if a lawyer’s professional judgment will be adversely affected by the lawyer’s own business or personal interests. NY CLS Jud Appx R 1.7(a)(2). As Henry wants to destroy the world and use Irving in some way to achieve that goal, this conflict of interest unquestionably would violate Henry’s ethical obligations to Irving.

Henry is also violating his duties to New York State and the US Constitution, with his active criminal conspiracy to kidnap his mother, commit murder, and bring about the end of the world. All of these actions would result in disbarment.

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Josh Gilliland
Josh Gilliland is a California attorney who focuses his practice on eDiscovery. Josh is the co-creator of The Legal Geeks, which has made the ABA Journal Top Blawg 100 Blawg for 2013 to 2016, and was nominated for Best Podcast for the 2015 Geekie Awards. Josh has presented at legal conferences and comic book conventions across the United States. He also ties a mean bow tie.

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