This is just speculating but there certainly are plausible answers to that.
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Originally Posted by Fish Taco
If he was the owner/scammer/etc why would he send Doug money in the first place?
To make it seem like a legitimate transaction sending funds to a player. If the owner sends funds from his insolvent business to himself he has to pay up when it goes in liquidation.
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Why won't Doug pay Blewjob his money? Why accept the money in the first place if you are just going to hold onto it and lawyer up?
It could be that Doug wasn't aware of the scam when he accepted the transfer but was when he was supposed to transfer it. I say scam because Jay blatantly ignoring the repeated question about the logs Skype makes it very clear he knows very well he's done something shady which he can't reasonably explain.
It's not about Blewjobs money here btw. The money is requested by Jay and Jay supposedly already settled with Blewjob. The whole Blewjob thing might very well be just another cover-up.