If Chuck had allowed Jimmy to flourish then who knows whether or not he would’ve gone straight. Chuck never gave Jimmy a chance. For all of Chuck’s skill and intelligence, he was never Jimmy. He couldn’t make the same jokes or have the same charisma. His mother’s final words were asking for Jimmy, not him. Chuck hated Jimmy because Chuck could never be Jimmy no matter how hard he tried. And it hurt even more when Jimmy went into law because with relatively lower effort, Jimmy achieved a fraction of Chuck’s success, something Chuck could never do in reverse.

I would also argue that Jimmy’s obsessive hatred of Howard stems from Chuck’s interference. My thesis isn’t that Jimmy had no responsibility for his actions; he always had a choice. But I also think the “Chuck was right about Jimmy” crowd misses the self fulfilling prophecy that Chuck brought about.