Worst Problem with Playing D&D with Your Boss and Co-Workers Is...- GM 911

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Worst Problem with Playing D&D with Your Boss and Co-Workers Is...- GM 911
This Dungeon Master has unique problem.
Original Post-
Hello there Nerdarchy. Long time watcher, and first time asking for something like this.

Recently at my place of work, I offered to DM a game. A bad move as I have only been playing for a few months but I had a story to tell and it's going well. Or it was. We have me and three players, one of which is my boss. We meet every week for about 3 hours after work and once a month for an 8 hour long 'super session'. He also occasionally brings his son in to play which is good fun.

Our problem lies here: As we were all learning we have come to the realization that there needs to be a dichotomy between what the Player knows and what the Character knows. To set things up, our first character death occurred this week. The player was a little upset but after some talk, he accepted the way things are. My boss, (the problem player) lent the dead player some money, (whose body has been lost). Out of character, he is demanding that the player's new character pay him back.

As an isolated incident this wouldn't be worrisome. However he is rather insistent. In Character he is constantly working against his alignment and Meta-Gaming the story as hard as he can. As the 4 of us have a rather interesting dynamic out of character, I wonder if you could provide some advice on how to deal with this.

Having watched your video on unruly players, I realize that the best answer is "Kick him out or continue playing with these issues." And if that is the answer you can best give, I'll take it into consideration.

Nobody wants him to leave, we just want to know the best way to straighten him out, or to perhaps have his character face consequences in game. This leads into a bigger question that I, as a DM fear killing his character for the possible visceral reaction or retribution.

This is a unique instance for me, and I apologize if my story is disjointed. Hopefully you can gleam where I'm coming from and I pray that you are able to offer some insight (Roll for it!) into my plight.

Thank you all for your time, and stay nerdy my friends.
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