It seems that you do not think honesty and objectivity will do the trick, so this is not even a remotely direct or upfront way to do it. Simply turn over the commissioner position to somebody you trust (who understands your predicament, agrees with your view and can keep mouth shut) who has been in the league long enough to make sense as the new commissioner. A new commissioner who does not work with or for him and can and will confront him and politely tell him to either knock off the nonsense or get lost. You play the good cop and take your boss's side in disputes. Show him you care and agree, but heck, you're not the commissioner any longer so your hands are kind of tied. If he doesn't stop, the new commissioner quickly boots him (to save on drama). Argue (for your co-workers' benefit) that it was unnecessary and that he should at least get his entry fee returned if he's is booted. Later (perhaps the following season?), the new commissioner can "flake out" and turn the league back over to you. The leagues I play in have a tradition that if you are kicked out, there's no getting back in. If yours has a similar tradition, simply take advantage of it. Even if it doesn't, most people I know would rather eat glass that try to get back into a league from which they had been booted. Why would he? Hopefully he will stop acting like a tool, but if not, and if parts are played right, you just might be able to have your cake and eat it too. If this guy is half the jerk you've described, the other co-workers will be equally happy to be rid of him during their off hours. Again, I appreciate that this is somewhat less than forthright, but it seems that your circumstances otherwise mostly preclude you from salvaging a good result.