I highly doubt Overstock had any such stuff, but does not mean he is not DS and I will explain why.

When he launched Overstock, he could have taken the easy route and gone with the Wall Street way - essentially giving control of the IPO shares to the wall street banks, who would gouge the value of your company and make tons off your hard work.

Instead he decided to launch it himself with some independant banks/financial types. Only when he did this, did he find out how entrenched Wall Street was, when he realised he had painted a target on his bank, and everyone was trying to bring him down. Thats the first time he understood how they used naked short selling and other shenanigans to bring down any company and destroy them without leaving any traces.

He then became a federal informant trying to bring down the Wall Street and in the process learnt a lot about the corruption not just in Wall Street but also in FBI.

My belief is, if he was doing things like Wayfair, he would not have caused ripples, rather go with the flow and enrich his own pockets. Also, he wouldnt have tangled himself with FBI.

But here is my thinking - he started off idealistic, but probably realised how deep the swamp is. He then became a side player in it, with the Maria case, and Hillary/Trump/Russiagate etc. I think this is when he got compromised and became a plant into the Trump camp. He had all the credentials, he had fought the swamp, he was a democrat turned republican, and he was independently wealthy. With this combination, he would have been very tempting target for [DS] to use against Trump. My guess is, at that time they found something incriminating on him and managed to turn him. Maybe he tried to protect his girlfriend Maria-whats-her-name and ended up compromising himself.