Youngtradersla,
I don't think anyone can add anything useful to the closing trades that you listed. However, for the following opening trades, to aid the discussion it would help to know your sentiment and forecast for price and volatility at the time of placing the trades:
5/8/2006 9:32 Sell To Open 4 .CYQEX CSCO MAY 22.5 Call 0.2 65.04
5/8/2006 9:32 Buy To Open 4 .CYQFX CSCO JUN 22.5 Call 0.45 -194.95
5/8/2006 9:32 Sell To Open 4 .CYQQD CSCO MAY 20 Put 0.1 25.04
5/8/2006 9:32 Buy To Open 4 .CYQRD CSCO JUN 20 Put 0.2 -94.95
This was a double long calendar on CSCO. Postpone discussion of this till after the MSFT calendar has been dissected.
5/4/2006 15:58 Sell To Open 2 .NSIRK NTRI JUN 55 Put 0.95 175.04
5/4/2006 15:58 Buy To Open 2 .NSIRL NTRI JUN 60 Put 1.85 -384.95
This is was a long PUT vertical on NTRI. Long gamma, short theta, long vega and short deltas i.e. you were bearish on NTRI. The position decayed but had the potential for small gamma to expand quite nicely in your favor.
Debit for the 5 point vertical was $0.95 meaning a maximum profit potential of $4.05 at expiration if NTRI finished below $55 which it did!
This trade should have been a big winner. It had a lot of leverage being an OTM debit vertical with approx 1:4 risk/reward.
I can only assume that the trade was closed prior to expiration after the head-fake on the May 10th perhaps. Given that the trade was a bit of a lottery ticket, a possible reason for being shaken out of the trade was due to using a position size that was too large. You might want to consider using the entire debit of the trade as the stop loss and therefore using a smaller position size versus using a larger position size and cutting losses when the PnL reaches a certain point. Hope that makes sense.
5/3/2006 14:11 Sell To Open 10 .MSQEJ MSFT MAY 25 Call 0.05 34.99
5/3/2006 14:11 Buy To Open 10 .MSQFJ MSFT JUN 25 Call 0.15 -165
This was a long calendar on MSFT. Long calendars are net long vega due to the back month option outweighing the front month option i.e. you are buying volatility here. This means you have to think that volatility has the potential to
increase after the trade is placed.
The position was also bullish given that the $25 strike was OTM. You may or may not be aware that implied volatility tends to decrease as the underlying rallies (for equities). This puts the position at odds with also being long vega (wanting volatility to increase). Therefore, OTM CALL calendars are usually not a very good play under most circumstances IMO.
Calendars are most profitable when the underlying finishes at the short strike of the front month. This did not happen in your case.
It is usually a good idea to keep an eye on the short front month leg to see how much hedging power it has against the long back month. As soon as it looks as if it is no longer providing any hedging potential it is prudent to start thinking about adjusting the position. A possible adjustment would have been to roll the short front month option to the JUN 24 strike resulting in a bear short vertical on the back month.
Any adjustment you make needs to result in a position that you
want to have and is consistent with your forecast at the time. Did you remain bullish on MSFT as MAY expiration closed in? Also, the adjusted position should not cost more than if you had to open the position from scratch at that point in time.
In the case of this calendar, it could just be the case that you got the forecast wrong on where MSFT would go. It happens.
There is a thread here on ET that had some coverage of calendar spreads:
http://www.elitetrader.com/vb/showthread.php?s=&threadid=58716
That might provide some further insight over and above what you already know.
Good luck. It's difficult to ascertain your level of options knowledge as you seem comfortable using various kinds of spreads. The problem may just be bad luck/inability to forecast underlying/volatility hitherto or perhaps position sizing and adjustment methodologies.
Further reading that you may consider:
Option Volatility and Pricing by Natenberg
Options: The Hidden Reality by Cottle available at
www.riskdoctor.com
Those should solidify and round out your current knowledge before you move on to more advanced topics IMO.
2 Cents.
MoMoney.