It is rumored that Draper is going to bid for the coins being sold in this auction as well. Also IIRC bitcoin was trading around $650 when the USMS announced that one person won the all of the coins in the auction and bitcoin is now trading at around $380 so he lost closer to 40% then 2/3 of his money. It is also not known how much of a discount he got from his winning bid.
He ain't lost anything if he hasn't sold. What I heard is that he actually paid a bit over market for them. Considering that he could have paid a lot over market with even splitting it to 500btc orders, I think it was a theoretical win.