Hi Gary,
not a lot substance to it really, but I'll have a go, and Grandiron was a nod in passing to Bimble ;-)
On 9/11 I had trades open - the markets shut (memory, perhaps false, insists they closed like steel shutters slamming down) and stayed shut for days... they reopened with a significant gap down. Now, short players did well there - I don't recall any arrangement to be fair about it, ie short players did well, longs generally got slaughtered, and there was no opportunity to get out as stops were ignored as the price jumped past. (Guaranteed stops excepted).
In a smaller way this happens with profits warnings, which are rather more common events - the one I remember best (I've not experienced many, thankfully) was Honeywell about 2001 or so... I had a long trade, it was trending up like it was trying to create a perfect 45-50 degree slope, closed around $40 one day and posted an after hours surprise that saw it open at something like $28 the next day. Bad enough holding it long in shares, a 30% or so drop but imagine if you had a spreadbet on it that was open overnight - that's a $12 or so drop, at the minimum £1/pt I' m used to currently that's a bet I'd have been looking to make maybe £50 from that suddenly turns into a £1200 loss!
That sort of thing can happen - there is a risk that any one share might plummet and cost a lot to get out of, and a stop won't necessarily work unless guaranteed or you have the opportunity to exit at the chosen price, gaps prevent this, and gaps are common - some of us scan for opening gaps as a daily trade opportunity so they're hardly uncommon.
It's a case of figuring out what it's possible to lose, and how likely it is to happen - a 9/11 event will perhaps halve all stock prices, so you could hedge against that by simply ensuring you have a reasonable spread of long and short trades - the shorts would hopefully compensate for the losses in the longs, or at least take the sting away... you can diversify your holdings and reduce risk by trading different markets and sectors simultaneously as well, so a big problem in say the drug companies only affects part of your holdings.
By spreading the risk you are limiting the number of events that can wipe you out . Over and above that you can take a significant hit to more than one stock at once, stocks in the same sector will often move together (you'd think that bad news for Tesco would be good news for Sainsbury really, but it doesn't seem to work that way <g>) so if stocks are closely related and you are long the pair then you stand more chance of having two big drops than if the two are unrelated - when did Tesco's results last affect Vodafone?
So, if you reduce risk by diversifying your holdings, and reduce it further by trading both directions, you are no longer (IMO) at 100% risk of loss - you may well get stung, but not fatally. If you then decide that maybe you'll estimate a worst worst case is a day where you can't exit and you lose 25% of your pot, I think you'd be nearer reality. If all shares lost 100% a 50:50 long:short policy should leave you neutral, provided everybody pays up <g> You also have to figure the economy and civilisation are going to hell in a handbasket at the time so what use is money, and bank accounts etc will disappear into thin air anyhow - money, and share prices, only have a perceptual value, other than a small real worth as firelighters or fishing weights. No need to guard against that then, is there?
There are probably people who can quote percentages on this, I'd suggest you want a sort of central loss% number then stick a 1-2 standard deviation band around it, statistics ARE useful, but stick your feet in the fridge and your head in the fire and they're still wrong about feeling okay on average.
Dave