I think part of why Daisuke’s death impacted Jimmy the most out of the crew was because of a few things that have to do with Jimmy’s ego and Daisuke’s attitude.
There are a few points that make it extra painful for Jimmy
1. Daisuke is the youngest of the crew and therefore has theoretically more life to live. It seems that the rest of the crew has a soft spot for him by virtue of this alone.
2. Daisuke does not have any prior history with Jimmy that causes any major beef with him. Jimmy is abusive towards Anya who’s terrified of him, and Swansea mutually dislikes him and seems to see how irresponsible he actually is. Daisuke is so new that he doesn’t have the context to know how awful Jimmy is. He probably doesn’t even know what Jimmy did to Anya.
3. Having his death be directly Jimmy’s fault in a way that cannot be spinned positively. Anya killer herself to get away from him, and Swansea was trying to rightfully kill him, but Daisuke actually did what Jimmy complains that his crew never does… LISTEN TO HIM. Jimmy laments that no one listens or does as he says, but Daisuke did! And he did it despite knowing that he probably shouldn’t. Daisuke gave Jimmy the benefit of the doubt and respected him as a leader and authority figure , and it ended up painfully killing him.
And it’s no wonder Swansea goes nuts and tries to kill Jimmy. Jimmy took this poor naive kid and knowingly put him in danger, KILLED him, to get what he wanted. Instead of risking his own life like the hero he supposedly wants to be, Jimmy has to send someone else to do the hard part.