My Best Trade Ever And The Critical Lesson It Taught Me

Markets break.  Not like “break lower,” but actually break.  The mechanics of the market break.  Think “flash crash” and the recent Facebook IPO.

Do you know what to do if the mechanics of the markets break, even for a short time? I do, thanks to a very memorable trade.  My “best” trade ever.

I say it is my best trade ever for a number of reasons; some obvious, and some not so obvious, all of which I will talk about in a moment.

I used to be addicted to ice.  Not the frozen blocks of water you put in your delicious and refreshing summer drinks, but the Intercontinental Exchange ($ICE).  I used to trade $ICE like a crack addict, drawn into its once wild volatility.  If it is ever really possible to know a stock’s personality, I knew $ICE’s cold.  Get it…?  Cold…?


It was September 18th, 2008 and the markets had been going through the type of extreme daily moves never before seen.  This was a Thursday, the Thursday before options expiration, and there had been some rumblings on CNBC about a short selling ban.  If memory serves me right the United Kingdom may have already enacted the ban on their financial stocks, but whatever the exact circumstances, I just had a gut feeling that the same thing could happen in the US.

So I went to my “go to” stock, $ICE.

$ICE was trading at around $75.00 just before the close and I thought I would take a flyer and buy the closest OTM calls which were the 80’s.  Because they only had 24 hours to expiration they were trading for just fifty cents.  I bought 10 contracts, fully prepared to lose the whole five hundred if my hunch was wrong.  I figured if I was right I might be able to make a couple grand.

And in fact, after the market closed the SEC did ban short selling in 799 different financial stocks for three weeks.  $ICE was one of those stocks.

The next morning was insane as all financial stocks were indicated massively higher. Options don’t trade in pre-market, but it looked like my “lotto ticket” calls could be worth some serious cash.

Once the market opened it was crazy.  “Dogs and cats living together” crazy.

$ICE opened at $87.84 and took off like a parabolic rocket.  $90.00…..$95.00…..I was now 15K in the money.  Sweet…!!!  But $ICE was just getting started.

$100.00…..$105.00…..$110.00…….One-Friggin’-Fifteen….!!!  I was 35K in the money on a $500 investment.  I’ll take 7000% return in 18 hours any day.

But something was wrong.  Very wrong.  The bid/ask on my calls had stopped at $13.30/$13.85.  This was not right.  They should be worth at least 35K.  I was owed over 21K.  WTF…???

I waited a bit, thinking maybe there was a data delay or something, but it didn’t move. It just stayed there.  I defiantly stared at the screen, perturbed that the market wasn’t giving me what I deserved.

And then suddenly a voice in my head said, “sex with twin Playboy models would be hot.”

I pushed that aside, but the voice continued, “close your calls out right now.”

I began to argue with myself.  No way I was going to sell here.  Sure, I would make an amazing profit, but there was no way I was going to leave 21K on the table.  2008 was a tough year and this was my chance to extract some rewards from a brutal market. Besides, $ICE was at $135.00, and how did I know it wouldn’t to $150.00 or higher?

“Sell your calls.  SELL THEM NOW,” my inner dialogue screamed at me.  I hesitated for just a moment more but then something inside me instinctually knew this was the right move. I hit the bid and was filled.

The markets began to calm down and most of the high-flying stocks came back to Earth.  $ICE ended up closing the day at $86.61, a little over six bucks in the money.

That night I heard an anecdotal story that explained why my calls never traded higher than the price I closed them at.

Apparently the options specialist backed away and stopped making markets right after the open.  The reasoning was that without the ability to short stock, they could not lay off risk on their positions.

I don’t know if that was the real reason or not, but it didn’t matter.  What did matter is that the market mechanics broke.  The options were supposed to be trading higher but they weren’t. There were unknown factors at play and when that happens, not only do you lose any slight advantage you may have had, you actually are trading with the odds stacked against you.

I got flat and took the profit I knew I could get, opposed to trying to get the one I didn’t know if I would ever be able to get, because the market wasn’t working.  If I had dug in and waited there is a very good chance I would have held those calls all the way back down, thus not losing just a theoretical 21K profit, but an additional 7K of real profit.

This trade was my best trade ever for a number of reasons.  Obviously from a risk/reward standpoint it was amazing.  And even though there was no real trade analysis of the set up, I do have to say that I was happy that I was “tuned in” enough with the market to take the opportunity.

But it is really my best trade ever because I did both the right thing, and the hard thing, by closing my position out at the frozen bid.  I felt that this trade marked a new level of maturity in my trading career.  And it left me with the critical lesson…..when when the market breaks, don’t hesitate, just get out.

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What bclund is, is the intersection of markets, trading, and life (with some punk rock, pop culture, and off-beat humor mixed in).

Brilliant stuff like this rains down like..well, rain, on my stream during the week. If you want to get wet, follow me on Twitter and StockTwits. You can also pick up my book Trading – The Best of the Best: Top Trading Tips For Our Times by clicking here.

  • Jonathan

    I think we’d all love some playboy twins

  • turd face

    This is an awesome story !!

    • Brian Lund

      Thanks buddy.

  • Doomdog144

    Amazing story, I was probably loosing my ass that week. I will remember that story if I am ever fortunate enough to have a great option trade!

    • Brian Lund

      It was a total lotto play. I take no credit for its success…lol.

      Thanks for supporting the blog man.

  • yo

    The mkt makers were net short going into that day?
    They won’t pay off. Deadbeats.

    • Brian Lund


  • ben

    Nice post Brian :) I made my best trade about 3 years ago when BHP wanted to buy out POT. I had also invested about $500 into POT 3 days before the news about a potential buyout broke out. The morning after the news was released, my POT IV exploded and i was over 1600% ITM. Best trade ever!

    • Brian Lund

      Very Nice. Thanks for reading the blog Ben.

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  • Rick

    It’s priceless to find and hear that inner voice that can be trusted. A truly hilarious and honest read of trader with the attention span of a squirrel ;) “…twin playboy bunnies…” Thanks for the reminder that like all man-made things, the market is not omnipotent and can break, and break hard. Love this blog.

    • Brian Lund

      Thank Rick. Appreciate you supporting the blog.

  • Jill

    Aside from your fantasies about incest, very helpful post. Thanks for explaining what “the market is broken” means.

    • Brian Lund

      Now when you put it that way, it seems slightly less hot :)

      Thanks for reading Jill.

    • Nils

      What are you hating on incest? It’s a game the whole family can enjoy.

  • Nils

    Exercising them was not an option (haha, punny)?

    • Kid Dynamite

      yeah – very very odd… would have thought that even if bclund wasn’t allowed to exercise and sell long, that SOMEONE would have compliance that would allow them to do that….

      in any case, a great story – I had no idea they got that far out of whack. but I remember that day very well – I returned home late late the night before from a multi day trip to Vegas where I’d carried a MASSIVE short SPY and long SKF (double short financials) position which had huge gains early in the week which were wiped out by the attempts to intervene later in the week….

      • Brian Lund

        Two things were going on re: trying to exercise them. I had other positions in that account and probably didn’t have available cash to do it, and since things were moving so fast and mechanics were breaking down, I did even know how long it would take, or even if I would have been able to exercise them.

        When are the poker logs from your recent Vegas trip going up?

    • Brian Lund

      See response to KD.