When Rich first presented his question, several readers guessed he would be their parole officer.
Which was a good guess, but I only think that would work at a game table if the parole officer player was good natured about it, and playing it for fun, and not to be intentionally challenging.
In short, probably a bad idea with Rich.
I wasn't sure whether to have Ellen tell Rich to this in private, and considered either using the excuse that this was going to be a single game, and/or Rich being given the option to keep his reasons a secret.
Ultimately, I decided an uninformed decision isn't much a choice, and the right choice as Game Master would be to tell Rich in private.
Since Ellen is supposed to be pretty good at this, I decided that, yes, Rich was going to be told this in private.
Besides, there's more writing opportunities this way.