One of those characters I felt sorry for during the ENTIRE anime, all he wanted was to reunite his sister with her daughter, so they could be a family again. He had the most selfless reason for obtaining the Grail, but sadly rage and hatred overtook him.
Causing some of the grizzly events those of you who had seen the show have witnessed and propably pitied the poor soul during all of them. without a doubt Kariya suffered the most out of all of them, and was by far the most ill experienced (except for rider's master).
i kinda agree, but ehat Kiritsugu wanted was something impossible (as the Grail itself showed him) and i think that Kiritsugu needed to learn that his ways we're wrong (which he did, when he nearly broke after seeing the disaster he caused, and cried in happiness when he manage to save a single person). i think Kiritsugu was too "pure" to have the Grail. I think Kariya deserved the Grail for having a more realistic noble goal.