I agree with the respect comments as well. I think that if you had gone over the rules about how you were managing the land, then he just flat out ignored that. One of my best friends had the minister from their church hunting with them for one year and they had to get rid of him for the same reason. The night before season that went over the rules with the guy, because his reputation had preceeded him in his greediness, and come opening morning the guy shoots a spike, a 3-point and a doe. The minister used up all his free passes that morning and that was his last time at their camp. I think your friend should be treated the same way, one more jackass move and he's done. What's even harder to believe is that he shot a button when there was a brute known to be in the area. When it all comes down to it, you have to make the decision on how to handle it, and it can be very difficult among old friends, but its still your land and your work putting stands out so he needs to respect what you are doing for him, far beyond you having to be careful about not offending him because you got him into the sport. If he is bowhunting because of you and looks up to you as a role model for the sport, then following the rules you laid out needs to the top priority for him. Good luck in resolving the situation.