Silliest trade (and interesting related story):
In early December I'd lost money on some POT trades trying to catch a falling knife. My account was with Etrade and I paid $16 round trip on every trade, so scaling in and out of trades was cost prohibitive commission-wise. As a result I always traded 1000 shares, and did so with POT as it continued its eternal fall from grace.
Frustrated with trying to time the stock's bounce, I decided to buy 5 POT $55 calls late in the day on 12/4/08 after POT had fallen 5 days in a row to below $50, figuring that was a ridiculous price for a stock which had traded 6 months earlier as high as $240. Surely it had to bounce and options gave me a couple weeks to take advantage of that with a fixed risk in place.
The next day POT not only opened gapped down over a dollar, it continued to drop! I had a moment of irrational fear that it might go to $0, and I remembered that when you have that thought, it's almost always the time to buy.
I had an appointment to go to, but figured I'd add to my option position before I left. So I opened my order entry window, selected the same calls I'd bought 5 of the day before and instinctively entered 1000 in the Qty field (remember I'd been trading 1000 shares of everything for months). Just as I was about to transmit the order I thought it would be wiser to wait until I returned from my appointment to add to the position.
At that moment I saw the 1000 in the Qty field and nearly had a seizure on the spot.
Had I transmitted the order it would've gone through immediately at market, and I've no idea how much slippage 1000 contracts of even a highly liquid option would've incurred, but even if the entire position filled at the offer it would've been $5000 for the spread, plus $760 commission one way. If I'd transmitted the ordered and realized my mistake, I would've panicked, closed the position at market and been sitting on at least a $12K loss.
However, if I HAD transmitted the order, I really doubt I would've noticed the mistake because I was standing up at my desk in a hurry to leave for my appt and likely would've clicked and left, thinking I'd simply added 5 contracts, a very low risk move.
So I return from my appt and see that POT bottomed out around $47, finally bounced a bit, putting my losing call position slightly in the green. Then price stalled and began pulling back. Oh, no, I thought, not another leg down! As the call premium moved back toward my break even point, I closed out the position for a net gain of $30 and decided I just wasn't going to trade POT for a while.
Well, that day POT put in its 52-week low and over the next 2 weeks rallied to $83 a couple days before expiration. The premium on the calls I had went as high as $27, meaning 5 contract position that I paid $1000 for would've been worth over $13,000 had I held it.
Then there's the other "coulda": If I'd transmitted the 1000-contract order, and held it through the rally, it had a potential gain of close to $3 million
How silly can you get? Closing a position so quickly whose MAX RISK was $1000!