I think Shinra is less despicable than Shizuo because regardless of his work and Mika's story and the idea if celty doesn't stay with him it will get worse.
but he has a much higher level of self-awareness than Shizuo and bc he doesn't justify himself we think he's more despicable.
Also, his lack of concern for anyone but Celty makes him fair and unbiased.
We all know how horrible and murderous vorona is, also kidnapping and hurting children and trying to shoot Shizuo, yet he still treats her like an angel and a child. This is absolutely terrible.
Even Izaya didn't excuse Nami's actions, despite his love for her work skills
I have always loved people who have self-awareness, no matter how vile they are, still better than those who constantly tell you that they do not like violence or anything bad and want to change, but they return to the same cycle.
I get where you're coming from Anon. Like I said, I struggle with exercises like this where I weigh morality/deeds. I think Shizuo is a scumbag in his own rite. However, I don't think Shinra's self-awareness saves him anything and while I agree to some extent that the fact he only truly cares about one person makes it easier for him to be objective, I still think a self-serving person like him is more despicable than someone who has no goals whatsoever and no ill intent whatsoever like Shizuo.
Personally, I think Shizuo's worst crime is his self-righteousness and his tendency to condemn people once and then write them off forever. And conversely, I think the fact he excuses the actions of characters like Shinra, Vorona, and Kujiragi are also problematic. If that is his worst offense, whereas the other people lower on that list are people committing heinous crimes against other people (not saying Shizuo's property damage and injuring others isn't a crime. Just also noting that he has no intent or goals behind his crimes), then I don't feel right putting him below any of those people on the list.
With that said, I am also conflicted about my placement of Mikado, but I put him there because Mikado had good intentions behind what he did, and ultimately I personally was not upset by any of the crimes he committed as the leader of the Dollars or Blue Squares but that could just be because of who I am as a person lmao.