It does seem likely that a gang was involved because there seems to be infrastructure...really lame infrastructure, but teams and individuals with assignments, etc.
JW doesn't appear at all on any level to be a gang member. Is it possible that his old neighbor caught on to JW's new job working for SS and the gang voluntold JW what his role would be. That would be lose-situation. If he says yes, he's suddenly a criminal helping a gang (although putting enough money in the wallet to get through a couple races. If he says no and goes to LE, he's toast. It might not be too hard for a broke racer to reach the conclusion that he's got to participate.
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Would make it highly unlikely that JW would have pocketed half the ransom money - or, it would explain why he hasn't been seen if he did - could be in protective custody.