Did Bobby really have a reputation as being a good earner? Not sure about the accuracy of Wiki, but here is what was written about him....

"Tony had recently stepped up his expectations of Bobby, whom he felt was taking their brother-in-law relationship as an excuse not to earn at a competitive level, compared to other members of the family. Bobby rose to the occasion by supplementing his income with $7000 he received for shooting a rapper he met at the hospital, while Tony was in the ICU, in order to raise the rapper's profile."

In addition, in one scene at the doctor's office, Junior was complaining to Tony to get additional funds to pay for his high priced lawyer. Tony advised Junior to get his shy in order if he wanted to make more money. I think Bobby may have been in charge of running that for Junior, and if so, he wasn't doing a very good job.