Don't the five families have a lot more involvement in the drug trade than the outfit? And everyone knows drugs are the most lucrative.

In Chicago the Sinaloa Cartel in conjunction with the largest street gangs (Latin Kings, Gangster Disciples, Vice Lords etc.) totally dominate the drug trade, so its impossible for the Outfit to take advantage of that market the way the Italians do in New York

Also much of the Outfit money has gone legitimate as has been stated..real estate, restaurants, construction and sanitation companies, lingerie bars and even farms downstate