That's an abuse of flagging. I wouldn't be surprised if the moderators have your flags going straight to /dev/null because you're using it to mark earnest content you disagree with.
No it's not. Read the guidelines. Half the garbage he writes is just fanboyism and doesn't even meet the "interesting" criteria. In fact, similar fawning crap by other writers are even autokilled, but because Gruber writes about Apple his stuff lives on.