One of the things I like about Fisk, as a character, is that he is a subtle and nuanced villain. Part of that is that I think his attitudes and feelings toward violence are context-dependent.
Does he enjoy directly inflicting violence and pain? Highly likely. I think it is less about the cruelty though, and more about cutting lose and giving into (maybe learned) instincts for violence. Here I'm thinking about his temper-tantrums, such as the infamous car-door incident.
That said, a part of it (at least with Matt) might even be a joy in the physicality of the fight itself. I would be surprised if he didn't have some sort of formalised martial training. No way could he hold his own without some sort of training, even with his size, against a Stick-trained Matt.
As for the "regrettable" cruelty, I think he sincerely regrets individuals caught in the cross-fire of his plans. He doesn't take pleasure in the abstract suffering of others. That would be pretty awful, even for a villain. While he may enjoy hurting someone with his bare hands or winning, I don't think he would enjoy the idea that random innocent people are casualties. He doesn't care enough to stop his plans, but he doesn't want the people whose lives he's trying to "save" or "fix" to suffer. I imagine him feeling a vague and nebulous unhappiness, sort of like how a person feels after seeing a news-story about wars happening overseas. I think there is a level of disconnect for him.
However, at the end of the day "author convince me". If someone writes a sadistic monster Fisk well, I will endorse that head-canon. If someone writes him as a conflicted and tortured soul believably, then I'll support that too. Simultaneously, if need be. The truth is probably somewhere in the middle. People are complicated and the best characters try to emulate and reflect that complexity.
Re: Fisk says he takes no pleasure in giving pain
Does he enjoy directly inflicting violence and pain? Highly likely. I think it is less about the cruelty though, and more about cutting lose and giving into (maybe learned) instincts for violence. Here I'm thinking about his temper-tantrums, such as the infamous car-door incident.
That said, a part of it (at least with Matt) might even be a joy in the physicality of the fight itself. I would be surprised if he didn't have some sort of formalised martial training. No way could he hold his own without some sort of training, even with his size, against a Stick-trained Matt.
As for the "regrettable" cruelty, I think he sincerely regrets individuals caught in the cross-fire of his plans. He doesn't take pleasure in the abstract suffering of others. That would be pretty awful, even for a villain. While he may enjoy hurting someone with his bare hands or winning, I don't think he would enjoy the idea that random innocent people are casualties. He doesn't care enough to stop his plans, but he doesn't want the people whose lives he's trying to "save" or "fix" to suffer. I imagine him feeling a vague and nebulous unhappiness, sort of like how a person feels after seeing a news-story about wars happening overseas. I think there is a level of disconnect for him.
However, at the end of the day "author convince me". If someone writes a sadistic monster Fisk well, I will endorse that head-canon. If someone writes him as a conflicted and tortured soul believably, then I'll support that too. Simultaneously, if need be. The truth is probably somewhere in the middle. People are complicated and the best characters try to emulate and reflect that complexity.