All I can say is
all denoms from both issues seem to have been showing up frequently on ebay for a while now (I just bought a load of them myself hence I was 'familiar' with them) and the chip rack value is overstated. James values them at $20-$50.
There were actually no $1's in the quantity (although I know the person with all of those anyway), they were $5, $25 and $100, and many were uncirc, the rest in pretty good condition from what I saw.
Both the buyer and seller would have been well aware of the value of the chips changing hands.