Of course you don’t see the problem with challenging the past! As I said from the beginning you clearly don’t align yourself with the views and traditions of the past. Obviously if that’s the case then you won’t mind challenging said views and traditions; they run contrary to urs
The whole idea of the portrait is to merely represent yourself as someone who held the office. You’re not meant to be more memorable based on your portrait; but rather by your actions and how society views you later on.