Kakashi Hatake was a man of many vices and few virtues. Or at least, that is what he thought of himself. When Naruto became Anbu Captain a month after his training trip with the toad sage, he thought to himself: How badly have I failed this time?
He was happy for Naruto of course, how could he not be? His sensei's legacy was now one the best ninja in Konoha! And when Sakura had become the head doctor; he had felt unbelievably proud. His weakest student had now become one of the best kunoichi in the village!
But none of his "accomplishments" as a jounin sensei had truly been attributed to him. Things had not really come into perspective until he was assigned to test Naruto for his Jounin promotion. Naruto had single-handedly caused enough damage to the copy-nin that he was stuck in the hospital for 3 weeks.
His natural speed and shunshin exceeded Lee's Physical prowess by a light year, and his now long hair had reminded him so much of his sensei that he was blinded. He could have easily blocked, counterattacked, or brought out his Sharingan to level out the playing field, but he chose not to. Using his old teammate's gift, against the legacy of the sensei of the team that he failed? It was just wrong. And when Naruto came back from a mission with Sasuke tied up, gagged, and flanked with Anbu officers by his side, he began to feel just a little bit proud, even though Kami knew that he didn't deserve to.