It's hard for Diedrich watching Ciel grow up as the Watchdog because it makes him realize that all of the trauma that has turned this sweet kid into a much harder person is not so different than what Vincent must have gone through.
Some of it Diedrich knows because Vincent told him, but other things only make sense as an adult looking back. Ciel will say or do something that reminds Diedrich of something Vincent said or did at school. And as an adult, Diedrich can see how a traumatized child would react that way. Which makes him realized that while his teenage self was furious at Vincent, Vincent was probably experiencing shit like Ciel is.












