A well-dressed lawyer makes you a strange offer to change your name and mock a Sheriff

A well-dressed lawyer with a white leather eyepatch appears at your front door. He represents someone very rich and powerful who can completely erase any and all current, existing financial debt that you, your family and one personal friend have. He is able to verify this claim to you without a shadow of a doubt. You are not allowed to contact anyone and ask them to run up new debts or speak with anyone about taking this deal until the deal is completed.

In exchange for this total erasure of existing debt, he will ask you to do two things:

  1. You must legally change your name to Roy Tillman as of tomorrow morning. You are welcome to choose your new middle initial from any letter of the alphabet you want (i.e. Roy J. Tillman) but the name change is fully legal, binding and non-negotiable. You are not allowed to change your name back to your original name. The lawyer will be present to ensure the name change is done without any tricks.

  2. On the day after tomorrow, you must show up to an auditorium dressed like a country Sheriff (cowboy hat, jeans, vest, etc) for a local debate in a small, Midwestern American town, stating that your new name is now on the ballot for local Sheriff. The debate is for who should be elected sheriff in that town - either the current acting and popular Sheriff, Roy Tillman, or one of his competitors. You will show up along with two other fake "Roy Tillmans" who also took the same deal as yourself and each of you will be given your own podium to stand behind. The other two fake Roy Tillmans all look fairly similar to you - not so identical that people would mistake you for family but just enough that people might have trouble telling you apart in a line-up. You must introduce yourself as "I'm Sheriff Roy [Your Chosen Middle Initial] Tillman" at the start of the debate. Whenever the real Roy Tillman speaks, you must repeat whatever he says in a mocking impersonation. The moderator of the debate has also made a deal with the well-dressed lawyer to make sure that she will only ask the real Sheriff Roy Tillman questions that are insulting to him, so he will be made upset and you'll then have a lot of chances to parrot his answers mockingly. The debate will be televised, but only on local news channels. You are to keep this act up until the end of the "debate" or until Sheriff Roy Tillman gets too upset or frustrated and storms out of this farce.

All of the promised debt erasure will take place immediately at the end of the debate and you do not have to return to this town or see the lawyer ever again, regardless of however the subsequent election turns out.

Some important caveats:

A quick online search reveals that the real Sheriff Roy Tillman is an extremely charismatic and attractive man who is beloved by most of the people in his local small town. He has an extremely well-armed local police force that zealously obeys his every command. He also has a strong web presence where he is beloved by a small group of online radicals who love him for how he presents himself and his extremist views. Underneath his charming, folksy facade, he seems like he might be quite dangerous. Since the debate is being televised, you are almost certain he will not take any immediate action against you during the debate, but he and others will now have your face on a recording to review.

Both his local police force, some members of the small town and the online group who adore him will likely be offended by the sham "debate" you are participating in and they may try to find and harm you afterwards but A) they currently have no idea about what the lawyer has planned or B) what your name was before you just changed it. The well-dressed lawyer tells you that you will have at least two hours before the news of the debate becomes widespread and offers to drive you out of town immediately afterwards but offers you no additional protections beyond that. Assume you can make it to an airport or local train station before the two hours are up.

Do you take the well-dressed lawyer's deal to change your name and make fun of a popular small town Sheriff in exchange for the total erasure of your debt, your family's debt and one friend's debt?

Posted Sep 13, 2025, 10:54 PM UTC

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