I think we're splitting hairs here. In any event, regardless of any tactics, strategies, or arguments they use, he is sure to be found guilty on most, if not all, of the charges.
[1] http://www.justice.gov/sites/default/files/usao/legacy/2013/...
If not, how much would you put at risk for the chance to win $1 if he is convicted?
As for betting with you over the internet, that is a violation of the Interstate Wire Act, and I have no intention of being cellmates with Ross Ulbricht. But, for example, if this bet were offered in a legal sportsbook in Nevada, I would easily put up $10K to win $100 (for a 99% certainty - trying to win $1 is a bit of a fruitless exercise). I believe that I would have a positive edge on that bet.