Michael never truly followed through on his earlier pledge to lead the family business into legitimate enterprises. When Merle Johnson who was dating Connie wanted to discuss a business opportunity with Michael he refused to talk with the man and ordered Connie to break up with him. Although we'll never know Merle's opportunity might have been a good legitimate business opportunity for the Corleone family. Sad that Michael never gave Merle a chance to tell him what his idea was. There might have even been a place for Fredo in such a business.