It's no secret that Obama believes in the virtue of the collective. And during his administration he's made it clear how embarrassed and shameful he feels our collective past has been in America. I'm sure he see's this as being "humble".
But humility by definition, can only be a personal virtue. When it's foisted on us by our leaders it's not virtuous humility, it's just collectively humiliating.
This is no leader - this is a man who is giving real leaders what he see's as their comeuppance. More than anything else, he's a man who does not deserve to be in charge of anything.