It is a wonderful thing and there is a lot more hindsight to be found! In terms of shorting: you could of course always make a private bet with an optimist. It would be interesting to think in detail about how such a bet might be structured. Another option would be for you to approach a large merchant and ask them whether they'd be willing to lend you say 5 cases of Lafite (or any other wines in a vintage you'd like to short). The merchant could temporarily transfer ownership to you against collateral (and you'd also pay a rental fee). The cases would then be yours to sell... Hope that the price falls, buy the wine back and return it to the merchant. This is how it works, unless you are into "naked shorts"? Ideally you'd want to do all the above without any physical movement of the cases... Technically all the conditions exist to execute a trade like this, but you'd need to be brave and a bit creative to be the first, not least because of the spreads.