I find it so interesting that, while Rocky did deeply involve Freckle in the Lackadaisy underground crime business, he actually tired to hide it from him at first. Until he gets desperate.
In the chapter Surreption, when Ivy suggests bringing Freckle to the Lackadaisy, Rocky IMMEDIATELY shoots her down and says he has things to do
of course, Freckle goes anyway once Iy slips him a clover pin and then Rocky gets Freckle involved deeper when he sees Mitzi and Wick kiss in the chapter Rendezvous
hes DESPERATE to be kept by her and this desperation leads him to drag his cousin down a dark path in Pinstripes
but even then, in Bookkeeper, Rocky all but promises Freckle that he won’t have to shoot anyone again and that his job will just be for looks
…which then turns out to be a lie when Rocky gets desperate to not be replaced by Wick again when Mitzi says Wick and his money saved them again in Camouflage
this causes him to craft a plan where Freckle will kill Fish and Wes (this is also a day after the head injury, so he might also not be in his right mind), not only going back on his word but FURTHER leading Freckle down a life of crime
The thing that motivates Rocky to dig himself and Freckle into the crime life is desperation and the fear of being replaced by Wick
I just remember when there was a time he tried to protect Freckle from all of this - before he got desperate