Naruto: terra cognito
Kakashi, like Napoleon, grew up during a period of war. To him, it seemed as if everyone he knew at that time became either a legend, a hero, a traitor, or a corpse. Kakashi became part of the 1st category, never ambitious or filled out enough in his personality to be a hero. Obito, true to form, became part of the last category.
Kakashi, like Napoleon, went up the ranks quickly, a slave to his own intelligence and ability. But Kakashi never possessed the charm and ambition necessary to dominate the scene, to become a dictator, to lead.
In fact, it was Itachi who did, but Itachi was born in an era too wrong for him. By the time Itachi was 13 and an Anbu captain, the serious, dire need for brilliant young minds like Itachi and Kakashi was already waning to the bare bones. That's the truth of the matter, really. Given a time machine or a switch in dates of birth, Itachi could have changed the history of Konoha. More than he did, because of course he did, in his own, perhaps far more interesting, way.
Kakashi has never really met Itachi. Only once had he actually seen the boy. Itachi was, maybe, 13 already, donning the slim-fitting ill-fashioned uniforms Anbu captains wore, his cat mask in his hands, limp. It had been some kind of initiation ceremony. Itachi had stood on the platform admist a small group of other obscenely young prodigies, the statues of the Hokages behind them, stone-still. Kakashi, by then already old by the age standards of that time, made wizened by experience, stood in the crowd. He had watched only Itachi throughout the entire ceremony, not because he wanted to watch the only other Sharingan user in the Anbu troops or because he somehow knew Itachi would later commit crimes of blood and kin, would later slaughter his parents. It was because out of all the other young prodigies standing, Itachi was the only one who spent the entire ceremony staring straight ahead into the distance, never looking at the crowd, as if he knew exactly what his future was going to be, and didn't need anybody, least of all Kakashi, to tell him.
That's what Kakashi had thought then, anyway. Now he wonders if Itachi had seen anything at all, and if maybe that nothingness eventually drove him crazy, just like later Itachi would drive Sasuke insane. Kakashi doesn't know. Throughout Itachi's Anbu career, he and Kakashi never ended up on the same team, although whether it was from strategic planning or pure luck, Kakashi would never know. Sometimes he wishes he had once just shaken hands with Itachi, just to know at what temperature Itachi's skin kept itself, if it was normal and entirely human, and maybe to see if Itachi really existed before his murders and his betrayal made him come alive.