Not that he should have gotten a Pulitzer in the first place
but that fact that he got it for "Damn" is ####ing ridiculous. "Pimp A Butterfly" and "Untitled Unmastered" are clearly way more unique and interesting. "Damn" sounds like Kendrick made it specifically for fans who thought "Butterfly" was too "arty"- still unique because he's a talented MC but compared to the prior 2 releases it sounds so ####ing watered down and commercial. And if by "jazz connection" you mean jazz samples/influence, there's basically none of that on "Damn" but a great deal of it on those other 2.
I was similarly underwhelmed by him at first, mainly because I only sampled individual tracks. To really understand why he's considered such a big deal, you've arguably gotta listen to "Butterfly" in full and even then, it'll probably take multiple listens to really sink in (this was the case for me and I'm more of a hip hop fan than you seem to be).