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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I had considered that thought earlier but discarded it because I think there's no way a gang would allow anyone to keep that much of a percentage, since we don't know where the rest of the dough went. It appears that DW had more than half in the caravan. I think DW and friends was his own "little gang".
Hypothetically spitballing, assumes DW did not work alone (but no gang involvement), JW involved:
~ DW discovers JW works for SS (who had fired DW years ago) plan formulates in criminal pea brain.
~ Somehow DW coerces JW into providing intel. *snorts*
~ DW and playmates go to rob and plunder what they think will be lots of treasure and cash laying around and no people home, yay! The girls are playing dress-up (doubtful, but you never know what goes through drug-addled brains), everybody's going through drawers, closets hideyholes looking for anything worth flogging for a buck.
~ Idiot/s get there but find they're not alone. "What do we do now?" Tie everyone up. Think think think. AS "My husband can get you more cash, you can leave and go far way!" AS calls PS to come home, using code phrase "going out with the girls" PS races home in Porsche (seen by neighbor?) knowing something's up and thinking he can take care of it.
~ No (to myself) because most likely PS would call police while racing home? I don't know that they had code words or phrases or what they meant if they did.
~ I changed my mind, DW/SE (someone else) texted? PS and there were no code phrases.
~ PS gets home and is ambushed. The process begin to get cash from outside.
~ After DW found people at home, the ending was never going to be any different than it is.
If DW's intent from the beginning was to do the family harm, he would have done it at night and be gone before daylight. My opinion. I think this was meant to be a quick daytime burglary.
I will never understand taking the risk to yourself (idiot criminals) by killing people just because you could be identified and caught as a simple burglar. The sentence would be far less than kidnapping for ransom, assault, torture and murder.