Most you have lost off a single investment?

When investing or trading in any type of asset class, from securities and fixed income to even cryptocurrencies, you will always lose money at some stage, no matter how experienced you may be. Therefore I pose the question, what is the most that you have lost off of a single investment? Whether it was due to a miscalculation, a mistake, or just bad luck.

 

Lol $861? I have positions open currently where the month to month deviation from break even is several hundred more than that either way. I've had positions that were up $300 one month, down $1200 the next, and then got acquired leaving me with a 70% profit all considered.

If you're not willing to sit comfortably and bide your time while the market moves your three digit red into some sort of green, you might not have the temperament for investing outside of index funds and diversified ETFs.

Array
 

Not sure if this counts, but I had a 60% loss (on paper) on my portfolio for a few months on a single stock. Debated selling off the stock but held on because I believed the market was just being irrational at that point. Ended up selling it a month after with a slight profit. Still gives me the chills thinking about it. The problem was that most of my portfolio was in a single stock.

 

Yep. One can never tell when random circumstance or spooked bulls will saddle a good equity with red ink for the foreseeable future. The upside is that unless you're investing in garbage, odds are you can wait out the losses (if you have time to spare). Downside is that if you didn't diversify, you may be waiting a long time. For example, participants in the Facebook IPO had to wait 1.3 years for their investment to finally start seeing a profit.

Array
 

Trading crude oil in October I believe, maybe November... I was heavily short about 11 futures on around 30k... I lost about 28k between Friday and Tuesday... I was using the XOM:WTI ratio signal to short oil when the RSI is below 30. Even after that loss, I was positive ytd, starting with 20k in 2017 because I had withdrawn much cash and had cash around in different places. I had to rake up the money together and got back on track. I ended up closing 2017 with 18k profits on a 20k account, so 90%. Most of it was made on Crude oil

 

Much as I love my MBA and would do it all over again 1000x...

+SB. Very funny.

The truth is you're the weak. And I'm the tyranny of evil men. But I'm tryin', Ringo. I'm tryin' real hard to be the shepherd.
 

down low six-figures as a result of euphoric/mindless/historic market rally. continuously going long volatility since late 2016.
i'm a stubborn guy.

at least we all know a rally of such fervor will never happen in our lifetimes again.

 

about 6-8 years ago...lost 7mm (dollars) (while trading on a dealer desk) long the market...the market was choppy the day before, and so i bought the dip overnight with large size (i was junior in my career and didn't really know what i was doing)...and proceeded to watch the market selloff like a banshee until i got stopped out around 11am.
Was soul crushing...but also taught me risk management...and the concept of a market coiling...which is followed by a large directional release. This was the prompt i needed to start my education in technical analysis.

just google it...you're welcome
 

I loaded up on BAC (at $32) and WFC ($28) right after Wells bought Wachovia and BAC bought ML. My rationale being that the crisis was going to be bad but not devastating, the markets were overreacting, and the big guys would be even better positioned to rule the market after picking up two big platforms on the cheap. I still like the thesis long-term, but my timing was just a leeeetle off.

Ironically this segues into the best trade of my life, which was to load up on asstons of BAC at $3.10/share in the depths of the crisis to average my $32 purchase down (yes, I held it all like a moron). I bought so many shares that when I sold the whole lot at $16 a few months ago, I ended up making a bundle.

- Capt K - "Prestige is like a powerful magnet that warps even your beliefs about what you enjoy. If you want to make ambitious people waste their time on errands, bait the hook with prestige." - Paul Graham
 

I gave Barca goals at a discount for receiving Real goals on Monday... damn you Mourinho!

Jack: They’re all former investment bankers who were laid off from that economic crisis that Nancy Pelosi caused. They have zero real world skills, but God they work hard. -30 Rock
 
Opi:
my friend tricked me into trading a holographic snorlax for a diglett when i was 8.

Ah, pokemon.

Brings back so many memories.

It was a grade 6 pokemon battle. I took my best cards to school - dark charizard, blastoise, you name it. Needless to say, I destroyed my opponents and left school victorious. I celebrated by taking a bubble bath (bubble baths are the shit). A week later, I put my pants on (laundered by my mother) and noticed a slight bulge in my pocket. Curiously, I stuck my hands in my pocket and fou- WHA-MY POKEMON CARDS NOOOOOO

 

two trades wiped out my 5k account. the first when i bought four e mini s&p contracts at the high of the day. rode it all the way down for loss of 66%. the other day i blew up again and waay overbought e mini s&p's and crude oil..

blew up big time. futures and F'ing nasty.

 

I've had a lot of bad trades over the past 20 or so years, but the one that really sticks out in my mind was a D-mark trade in the late 90's.

I don't even remember how I had it structured, but it was some dipshit butterfly call spread or some such nonsense and I remember there were 4 legs to the trade. It was expiration day and the position was up about $32,000. We're into the last hour before expiration, where if I do absolutely nothing I pocket the $32k. But I'm monkeying with the numbers and I realize that if I lift one of the protective legs of the trade, I can make another $850.

That's right, $850. So I call the head of research and run it by him, he thinks about it and says, "Yeah, it looks good, but why fuck with it? You're already up nicely in the trade, and there's no guarantee something stupid won't happen. That leg is there to protect the trade. But if you really want the extra $850, go for it." So I did it. I sold the protective leg of the trade and made the $850.

Literally 5 minutes before the close, the market starts going berserk. The Bundesbank made a surprise interest rate shift and, without the protective leg in place, my $32,000 profit became an $18,000 loss in five minutes.

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I went heavy short right before March '09. I had a TON of AAPL & RIMM calls and they were just lagging and running a loss so I sold out of those longs, which were my only long positions, and stayed short. Needless to say, I got fucked on both of those. Just on the AAPL & RIMM calls I left about $75-80k on the table.

I went short end of August this year too - great call!!!

And then there was my infamous GOOG trade. The afternoon of earnings (also day before expiration) I had a feeling GOOG would put and put an order in for calls $50 ABOVE strike price. I think they were a strike of 500 and GOOG was at 450. They were something like .32/each. It was 3:57 and the order didn't execute and I was getting bored watching it trying to save a few dollars here and there. I cancelled the order. GOOG came out with earnings and teh stock went from 450 to 515. The next morning the GOOG calls I would've purchased opened at 33.00 form .32. I left about $120k on the table which would've been made in 4 minutes.

AWESOME!!!

 
tyrets:
I went heavy short right before March '09. I had a TON of AAPL & RIMM calls and they were just lagging and running a loss so I sold out of those longs, which were my only long positions, and stayed short. Needless to say, I got fucked on both of those. Just on the AAPL & RIMM calls I left about $75-80k on the table.

I went short end of August this year too - great call!!!

And then there was my infamous GOOG trade. The afternoon of earnings (also day before expiration) I had a feeling GOOG would put and put an order in for calls $50 ABOVE strike price. I think they were a strike of 500 and GOOG was at 450. They were something like .32/each. It was 3:57 and the order didn't execute and I was getting bored watching it trying to save a few dollars here and there. I cancelled the order. GOOG came out with earnings and teh stock went from 450 to 515. The next morning the GOOG calls I would've purchased opened at 33.00 form .32. I left about $120k on the table which would've been made in 4 minutes.

AWESOME!!!

I remember watching those calls soar. That was after the release of the Q2 earnings in 2008. To date, I don't believe I have ever seen a more profitable overnight trade.

 

I bought countrywide calls in 2007 when the crisis was just getting started, thinking that the stock had plummeted far enough, and that the servicing business was lucrative enough to earn the company's way out of the crisis, or make it an attractive purchase by another bank. I was wrong on that. In continuation of that, I bought all the banks when they were beaten down, thinking that some would have to bounce back in a big way. That has had mixed results. LEH went BK, GS paid off, BOA, C made a bit of $, etc... I haven't actually figured out my end PNL on all of those, though no major money was lost or gained, aside from a fairly big loss on Countrywide.

 

I blew up a $12K account on a series of bad option trades over the course of a month. I had about $2k left in the account and found a trade that I really liked. I backed out at the last minute and left $30,000 of profit on the table by not doing the trade. I made several poor trades fueled by emotion. I learned my lesson young and will not be making the same dumbass mistakes later in life when the stakes are larger.

 

Does worst trade have to be the biggest loss? I think my worst trade isn't necessarily my worst loser...

A few years ago UAUA was trading in the low teens. It dropped real fast and showed up on a few of my filters. I pulled it up and saw a large market order driving it down about a point. Naturally, I bought when the order was done, thinking the guy was an idiot. Then another one came. Now, I really think the guy sending these is an idiot - what a horrible way to sell stock. After a few seconds of calm, the waterfall starts. Market orders are tripping over each other to hit what's left of the bid. In a short amount of time the stock has dropped from ~$13 to ~$5. I find myself with on an open position $40,000 in the red. There are rumors that UAUA is filing for bankruptcy...again. No one knew what was going on. I think my price was ~$8, meaning a legit bankruptcy could double my open loss, which I wasn't too keen on. Slowly the stock traded back up and I managed to puke out for ~$12,000 loser. About a minute after I got out, UAUA halted. It turns out the story was printed in some obscure Florida newspaper. It was ~10 years old, reprinted with the current date - ie. complete bullshit. When UAUA started trading again it opened back around $12-$13, which would have been a ~$40,000 winner. At that point everyone was wondering at what point Nasdaq would break trades. There was a chance my sells could be broken, but not my buys...nope. All trades stood. That shit really sucked.

 
spoonfork:
Does worst trade have to be the biggest loss? I think my worst trade isn't necessarily my worst loser...

A few years ago UAUA was trading in the low teens. It dropped real fast and showed up on a few of my filters. I pulled it up and saw a large market order driving it down about a point. Naturally, I bought when the order was done, thinking the guy was an idiot. Then another one came. Now, I really think the guy sending these is an idiot - what a horrible way to sell stock. After a few seconds of calm, the waterfall starts. Market orders are tripping over each other to hit what's left of the bid. In a short amount of time the stock has dropped from ~$13 to ~$5. I find myself with on an open position $40,000 in the red. There are rumors that UAUA is filing for bankruptcy...again. No one knew what was going on. I think my price was ~$8, meaning a legit bankruptcy could double my open loss, which I wasn't too keen on. Slowly the stock traded back up and I managed to puke out for ~$12,000 loser. About a minute after I got out, UAUA halted. It turns out the story was printed in some obscure Florida newspaper. It was ~10 years old, reprinted with the current date - ie. complete bullshit. When UAUA started trading again it opened back around $12-$13, which would have been a ~$40,000 winner. At that point everyone was wondering at what point Nasdaq would break trades. There was a chance my sells could be broken, but not my buys...nope. All trades stood. That shit really sucked.

I remember that! We were sitting here watching it saying "WTF?" and then saw that is was a totally outdated article.

 

New to this, but true to this. Greeting all, i'm jumping in wallstreetoasis head first because i just love the street. anyway, one of my worst trades was shorting the spy fed day cause my momentum indicator gave a strong ass sell signal. Well, the fed pumped 600 gazillion and the market went against me. What did i learn, sit on the side lines fed day.

"Kept feeding him dollars 'till it all started to make cents."
 

Bought Fannie Mae at about $9.70. Went under 2 weeks later. Shares went to $0.25. FUCKING UNHEDGED.

People tend to think life is a race with other people. They don't realize that every moment they spend sprinting towards the finish line is a moment they lose permanently, and a moment closer to their death.
 
monty09:
'89 upper deck the kid for 91 upper desk jeff bagwell, 92 score frank thomas and 92 upper deck ben mcdonald

I used to collect cards, but after companies started to make premium packs and other inserts that raised the price of packs up to $7 when I was 12 I had to stop. I go for signed balls and bats now. My dog ate a donruss randy johnson rookie. Not exactly a trade but it killed me.

Worst trade: short selling NFLX a number of times. I'm never doing it again, which means that it is about to eat shit for all those who are interested in shorting it. It found ways to go up on days where the s&p was down 1.5%.

 
monty09:
'89 upper deck the kid for 91 upper desk jeff bagwell, 92 score frank thomas and 92 upper deck ben mcdonald

haha...ive got worse one...I bought 100 Gregg Jeffries 1989 Topps rookie cards for my entire life savings at that time. I was sure jeffries was the next Mickey Mantle. i was/am a Mets fan obviously.

I also got sucked in on some of those Ben McDonald olympic team cards if i remember correctly..

 

Worst trade...?

How about the one I DIDN'T make...?

Early March 2008, trading was very good for me at that time, but was starting to get headaches from staring at the screens all day (not just staring, eyes wide-open ogling -- you'd be amazed how exhausting it is day-after-day for weeks!)...

...so I decided to take a quick 2-week vacation to Bali (I'd be back 4ish days prior to expiry, so no probs) and the day before I left, I pulled up the options on a name I'd been following a bit: BSC. The stock had been bashed from the mid-$200s to about $150-$160/share, and I was rather bearish on it, but the cheapest options on the board were the March 90- or 95-puts (0.10-0.20) with about 3 weeks to go but I'm figuring that at expiry, the stock would probably be at, at worst, maybe $120, and I'd be spending every night in Bali (day in the US) looking at this thing and cursing, so I decided "Nah, I'll slap on the trade when I get back..."

Besides, the software our firm was using at the time wasn't easily installable/configurable on a laptop, and I really didn't want to try to mess with the markets from 10,000 miles away, anyway so that suits me fine....

So, I'm in Bali, wrapping up my last day of my vacay, and I flip on CNBC World, and I see that the markets are puking: down -3% to -6% across the board, and at first, I'm thinking "terrorist bomb?" but I turn up the volume and they're mentioning "weakness in the US banks, especially Bear Stearns" and then they flash the price:

        $45

OH FUUUUUUU - I should have bought those godd----d puts.....!!

I arrive in Narita, and hop on a terminal in the Free Softbank YahooJapan! internet cafe and I pull up the NYTimes.com site, and what's the Sunday headline: Bear Starns sold to JPMorgan for the princely sum of...

        $2

Waaaaaaahh....!

When I get to office, I'm expecting everyone to behave as if they'd won the Powerball lottery, so imagine my shock when they were hanging their heads and hiding behind their screens, and I'm like "wtf? Why the gloom. You guys made a friken killing while I was out surfing, I should be the one hiding..."

"Naw, man, we all short BSC vol."

"Whaa?"

"Everyone was - even the founding partners, they were short vol big-time"

I still kick myself for not slapping on those puts, that extra $900,000+ would've been nice....

 

How about another story to make up for my lame one:

One of the guys in the office at another desk managed to quietly flip 5,000 nickels (bought 0.05's, then sold 0.10's unhedged, back when bid/ask spreads were fixed 0.05- to 0.10-cents wide) on wings (wayyyyy OTMs) in YHOO, for a quick low-risk profit of $25,000 and the absolute Very next day, MSFT offers to buy YHOO for, like $45/share (I overheard the other guys one the desk jeering him "Still happy with that trade?" "F--- You!"; from what I heard, apparently he left at least $1 million on the table on that one...!

 

I do not add to losing trades ever so i've never had a real blow-up trade but my worst trade was being short a bunch of JGBs in early 2009 when people had japan in the cross-hairs as the next blow-up. The trade went well in my favor the first day i had it on and I added massively. Coincidentally my PnL had just hit a new high-water mark and so i went out to celebrate and left a call level with our night desk on the JGBs.

I ended up getting really drunk, staggering home and going to sleep, and then getting woken up 3 times during the night as JGBs ripped higher...by the time I finally covered at about 5am I had lost everything I made times four and was down big on the trade. It took me two months to recover the high water mark I made that previous afternoon. On a monthly basis my PnL really didnt show the hit because I had been up big on the month prior to this debacle but it was really painful psychologically. My lesson was not to celebrate high water marks until the weekend if at all.

 
Bondarb:
I do not add to losing trades ever so i've never had a real blow-up trade but my worst trade was being short a bunch of JGBs in early 2009 when people had japan in the cross-hairs as the next blow-up. The trade went well in my favor the first day i had it on and I added massively. Coincidentally my PnL had just hit a new high-water mark and so i went out to celebrate and left a call level with our night desk on the JGBs.

I ended up getting really drunk, staggering home and going to sleep, and then getting woken up 3 times during the night as JGBs ripped higher...by the time I finally covered at about 5am I had lost everything I made times four and was down big on the trade. It took me two months to recover the high water mark I made that previous afternoon. On a monthly basis my PnL really didnt show the hit because I had been up big on the month prior to this debacle but it was really painful psychologically. My lesson was not to celebrate high water marks until the weekend if at all.

thoughts on shorting the JBGs again here? I know everyone has always been on this trade and it never seems to work, but it seems like its shaping up to actually pay off this time. kyle bass has a particularly convincing argument

 

I lost a lot of money betting that Washington Mutual would get bailed out. Unfortunately they were not too big to fail and there was limited systematic risk.

 
vanillathunder12:
I lost a lot of money betting that Washington Mutual would get bailed out. Unfortunately they were not too big to fail and there was limited systematic risk.

I still own WaMu R-series preferred stock in my IRA (Now WAMPQ.pk). I bought some ~ $150s. I went on vacation thinking "They'll never let the largest deposit institution go down..." Doh.

It's been interesting watching them move during bankruptcy proceedings, though...

 

Liquidmetal Technologies Inc. (LQMT):

Longed @ $0.80, and then again at $1.18.

Rose to $1.76, then watched it fall to $0.60

All I would have needed was a stop loss, to bad it all happened within 3 days!

Yours truly, The Young Investor
 

I had 25% of my portfolio invested in a biotech, Celsion, and lost a year's worth of tuition.

"I'm blessed with an extremely poor memory, which allows me to deal with the future rather than the past." -George Soros
 

This a great thread, love it.

Don't have much to add except for the fact that I was still in HS during the crash, and instead of working on my projects in the computer lab, I was following the markets intensely, and was watching the bottom fall out of every financial. At the time, I had a few thousand dollars saved up from work, had already bought a car so at that point I wanted to use the rest of what I had to actually make some money. After the Lehman collapse, I was fairly certain that there was no way the fed. government was going to let that shit happen again - and of course by then almost every major firm was a penny stock. I had a very strong feeling that they were going to rebound very quickly, that there would be bailouts of some kind coming, and that at the least, there'd be a few dollar to be made pretty easily. However, my parents weren't a huge fan of this idea, and put a stop to that pretty quickly. Have done the calcs many times over since then, it hurts to think of all the money I could've made. Would've changed the trajectory of my life to be sure. Major lesson in learning when to take risk there.

"When you stop striving for perfection, you might as well be dead."
 

I was short a variety of those Ebola stocks during that whole craze on a personal account. I got bent over on multiple names realizing the loss on a few of them. The only one I ended up holding short was LAKE and even with its enormous breakdown after the craze died, I was still down overall on the Ebola short strategy.

I lost sleep during that month. You knew your names were just going to squeeze again the next day on anything even remotely related to Ebola.

 

Staying short on Glencore after it had crumbled 25% in September and they came out with a financial note. It went up 35-40% in the following 7 days.

Never discuss with idiots, first they drag you at their level, then they beat you with experience.
 

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