Sure, Jimmy got his law degree out of a cereal box, but he is still very much a passionate, intelligent, and capable lawyer (not sure what show you are watching). I wouldn't have expected HHM to hire him after he passed the bar even if Chuck hadn't forbid it.... Still, instead of mentoring his little brother, he cast him off. Instead of recognizing Jimmy's new drive, ambition, and work ethic, he only saw the good for nothing slacker brother he once was. He wouldn't even consider giving him the chance to do anything better than a mail room clerk. Why? Because of Jimmy's seedy past and because the law school didn't cost as much as his. I can somewhat understand his rationalization after Jimmy's hyjinks as a lawyer but then again Jimmy is cutting corners because of all the barriers to entry. Performing a harmless stunt to drum up business isn't really that bad anyway. If nobody is going to hire you because of lack of educational prestige, I can understand doing unconventional things to break through. Ultimately, you cannot justify Chuck keeping him out after all the work he does with the Sandpiper case(Seriously? No passion?). Putting together that case proved Jimmy wasn't just some mouth breather with a law degree signed with crayons. The only thing standing in his way at that point was Chuck's inability to let go of his elitist attitude and the past. He used to be a relevant and respected lawyer while Jimmy was a fuck up. He still clings on to this even though things have changed. The way he belittles Jimmy is so telling. Chuck isn't preventing him from joining HMM because he respects the law & the profession too much, its because he has never had any respect for his little brother.