Nagato was pretty much the leader of the rain.
Madara could have been first.
Orochimaru could, and would have, had he decided to make the effort to not slaughter people
Kabuto had no hope
Itachi dies of herpes.
Couldn't be as bad as what Hidan would do.
'Cmon guys, throw your god damn kunai at me, NO NOT AT MY FREAKING CLOAK YOU ASSHAT, THIS IS A COLLECTER, DIEE!