I'm pretty sure, in my case, that I was a factor in his sense of entitlement. I was a helicopter parent. If one of his teachers complained about him, I was sure it wasn't him, it was her. I intervened when I shouldn't have. This put the idea in his mind, 'ah...I can pit ppl against my mom and she'll side with me! I didn't do anything wrong, even my mom says so!' I take lots of blame. 
I think helicopter parenting was 'the thing' to do in those days of the mid-1990's to mid-2000's. Now, look what type 'attitudes' we are dealing with, with this generation of millennials.
So, yeah.
