To make somebody angry is to strike them in a way that would force them to be completely reactive. In doing so their ego must be the object of the attacks. It would require an incredibly personal and intimate knowledge of the team's best player.

I would require our front office to put together a committee who's entire purpose is to put together a profile of the target in order to best know where to start and what areas to target would be most effective.

Now the tough part is trying to target things that also wouldn't cross over the typical social norms within the game. Otherwise if that was fair game then really you could just say about anything else and get away with it to the detriment of your own reputation. Targeting somebody's family member, an incredibly personal aspect of their life or anything else that would be unacceptable in any other situation would go simply too FA.