What was your best/worst trade ever?

Forums are always a good outlet for war stories and to share miserable, miserable losses.

By far my worst trade was buying Global Crossing about a month before they crashed. It was a good lesson for me though. I didn’t understand the company when I bought it. Just got sucked into the hype. Bad outcome financially, but it made me a better investor.

Best trade is harder. I’ve had some that I’m very proud of. Anytime I nail my thesis I’m pretty happy. That doesn’t always work out to huge returns though. The best returns I’ve ever had were purely market timing calls using options on triple leveraged ETFs. But, I wouldn’t say I’m proud of those. That’s just gambling.

Best: Long USO in Feb 2009, sold it in July 2009

Worst: Long Lehman Brothers in Sept 2008

Long DZZ @ around $7 (picked up based on someone’s suggestion on this board)

I remember that thread: http://www.analystforum.com/forums/cfa-forums/cfa-general-discussion/91205364

I tried to warn everyone…

Worst: WaMu bought at $4/share. I bought WaMu, my friend got Citi at beaten down prices. Both were supposed to get bailed out. One did and one didnt. I got wiped out, he got handsome profit

Best: Long HomeDepot during a recent rally. Bought at $32, sold recently at $45, and it still grows.

Best: bought AAPL in 07 (?) just before iPhone announcement (@ $70 ish). Still holding now with 1 period of selling on a high and rebuying on a dip.

Worst: likely will be the options I’m holding in RIMM that are currently out of the money (though close) and expire in a couple of weeks. Runner up - though still undetermined - is shares in UUU (uranium) that have taken nearly a year to get back to my purchase price.

this girl at my work i should have asked out years ago…she could have been my wife. super classy babe.

@sweep …that was the thread, lost a few bucks :o)

my worst has to be Manulife…spent a month on it…made zero money…

Good things:

I bought some gold at $450 and then at $800. That’s worked out pretty well.

Apple has been nice, but I never stayed with it long enough to make lots.

Unhedged my portfolio within 3 days of the bottom in 2009. (But then sold stuff three months later, so missed extra rally juice)

.

Bad things:

In 2008, I hedged market risk before the crash, but didn’t calculate the hedge right and hedged only 1/2 of what I thought I’d done. I knew I should have corrected the oversight, but it was my first time hedging with double shorts and I was too timid. I would have been in a better place if I’d done what I’d intended to do.

My willingness to take risk is highly correlated with my ability to take risks, which has been low recently. Generally, that means I’ve had to learn a trader’s technique of cutting losses quickly. I don’t really cut them fast enough sometimes, but in general it has kept me from any horrific losses. So my portfolios are pretty conservative, and have relatively few home runs, but even fewer disasters. The challenge is when to put a position back on after having been stopped out, so sometimes my biggest regrets tend to be not having re-entered after having been stopped out. I’m still trying to come up with a sensible rule for re-entries.

bchad…how big is your portfolio? how do you manage to do all this hedging and stuff? you use options? futures?

Anybody has some kick ass Chanos types of stories ?

Best - bought Fairfax News Media Preferred (ASX:FXJPB) around $55 matured 2 years later for $100 par with all that juicy interest in the middle!!

Other best - got into a small co-operative prior to swapping to a corporate structure and am still buying at discount to net-net working capital due to apatheic owners

Worst - all of the bad ones seem pretty equal…there are plenty and all for different reasons.

My best and worst trade occurred within days of each other, in March 2009.

I day traded put options on DIA and SPY and returned 30% in one day. Once the market started to turn around after the Dow hit the 6000 range I decided to get more aggressive in puts and lost 50%. Volatility is a mofo.

Best: InterOil (IOC): bought at ~$35, sold at ~$70.

Worst(s): Sank $500 into a medical robotics company called Stereotaxis (STXS): I bought it at $3 and now its at $0.30 >_

I’ve started investing into St. Jude (STJ); the stock has nearly ereased all of it’s gains for the year on issues related to a retired product component. If more data comes out that implies some of the newer components have similar problems, it could cause a near-term headache for the company. That said, out of all its primary competitors (Medtronic, Boston Sci), STJ seems to have a considerably better pipeline ahead in less competitive market segments. BSX is going to see a decline in revenue out to 2013, with a two-year EPS CAGR of only 4% (not that meaningful since EPS is projected to go from $0.44 to $0.48). MDT’s two-year CAGR for top-line is better at 2.5% with EPS at 5.6% (going from $3.46 to $3.86 so more significant). By contrast however, STJ’s two-year CAGR for revenue is 3.4% and EPS growth of 6%. Yet, STJ trades at 9.8x 2013 P/E vs. 10.3x for MDT and 12.8x for BSX. Historically I think it’s traded around ~13x; if you discount for the product issue to say 11x-12x 2013 estimated EPS of $3.69 you get a $41-$44 target or a potential return of 12%-21% - not bad for a large-cap.

Best - UG (I love smaller, illiquid stocks that I can really set a value to) at 6 and change, 8, 9 and 10 over the years, selling some at 22, earning 5-8% yield along the way.

Worst - so many as they all stick in my mind - maybe LINC, misjudged the severe impact of the regulation and the mgmt.

i looked at St Jude etc as well…coudln’t wrap my head around the company for some reason (problably due to my ignorance on selling implants really)…

worst trade so far for me has been banco santander which i purchased in the range of 8.50-9.00 and more recently at 6 and change…

3 particularly sh!tty ones come to mind:

  1. ~March 2008, decided to buy gold futures as they broke below $1000 - woke up in the morning with no account.

  2. Many years ago, decided to short EUR/USD, figured it would come back eventually and could simply hold the short until profitable. After months of pain, closed out in a massive drawdown. Eventually, I would’ve been right, years later.

  3. Sold a dotm naked call in the 30yr, only to wake up the next day with it squarely itm.

Best trade: Hopefully never again making the mistake of overleveraging, ignoring timing/drawdown, and selling naked otm gamma.

…basically any silly behavioral thing they tell you to avoid in L3, I’ve probably done.

made about 1000% in one day on option expiration day and cashed out a serious 15k… GS criminal probe 2010

also was short emini sp500 futures during the flash crash 2010, but pnl was only like 2k