Why does Bullet ask Winter about Midnight as they plan their trip to Baltimore?

Bullet asks Winter about Midnight as they plan their trip to Baltimore because he found the bus ticket to Maryland in her coat pocket when they first got back together. He questions her about Midnight and admits that he has had a man keeping an eye on Midnight in case he was hiding cash or getting back into the drug business. Bullet tells Winter that Midnight lived very simply in Brooklyn and now seems to be a legitimate businessman.