In all actuality Bobby Jr. was not meant for that life. He was thrust into the mob solely off the reputation of his father.
I might be the in the minority but I didnt feel bad about Bobby. Sure he was nice compared to the other nutjobs in that circle but he was by no means an innocent. Especially in Season 6 he became much more ruthless. I remember when he killed that french dude the guy was gasping for air and he reached onto Bobby and he coldly swatted his hand away