He was an enlightened despot, at least, striving to improve his realm instead of seeing power as the ultimate end and letting the mountain he had authority over rot away while he and his cronies partied at the top. He brought Chicago into the 21st century with aplomb while other Great Lakes cities wither bitterly in the 1950's, good for him.
Though he was of course thoroughly convinced that he was the only person on Earth who could make Chicago better, that its citizens were his utterly dependent children and that he therefore had the moral right to do whatever he needed to to retain power, lest his children get lost in the wilderness. But this is a perfectly typical conceit among politicians. Chicago really is cleaner than it's ever been, for what little that's worth. And it's current position as an alpha world city wouldn't have been possible if Little Richard hadn't occasionally acknowledged the humanity of non-White Chicagoans, a major policy departure from his father.
Another major deviation from Dad is choosing to actually retire instead of dropping dead in office, which shows that he's at least sane enough to imagine existence without power, an increasingly rare thing among our modern political class.