Brother Bob has been feeling uneasy these days. Blackjack's sudden incident made him feel that something was really fishy here. Given Blackjack's years of operation in YODC City, even if he was involved in shady dealings and unable to connect with the authorities, his information network would certainly be very well-informed. If the police could take him down so easily, he wouldn't have survived this long, yet now he's been arrested just like that, and there's plenty of evidence.
It wasn't surprising for a drug dealer to get caught, and Brother Bob knew that someone like Blackjack would eventually be arrested one day. Hence, he usually stayed out of Blackjack's affairs, strictly avoiding any connection with him.
If it weren't for what happened that day, Brother Bob would have thought it was normal. But on that day, Blackjack had just had a conflict with James Brown and then was taken down. This made him suspect that James Brown had something to do with it.
