Thanks.
I do hold 2003 and 2004 calls. The 2004s, I intend on holding till about June 2003, or perhaps exercising them just before expiration (if I continue to like the LT story, and they are far in the money).
I would try to sell shorter-term calls, when I think the stock has had a big ST unsustainable runup, and I want to limit my risk in case of a big pullback. I would probably just let them expire (hopefully worthless). I haven't found any specific discussion of this scenario in any tax book, or in any IRS publication (and I've looked). I think I could argue that two calls (same stock, same strike price) are not "substantially identical" if one has an expiration date 2-4 months out, and the other is 2+ years out.
If I sold some nearer-term calls, and the stock kept on going up, then (when I get called), I would probably also sell some of the 2003 calls I already hold, at the same time.
And, as you say, if the transaction in the shorter-term calls is in 2001 and 2002, and I hold my longer-term calls till 2003 or 2004, it's unlikely the IRS will even notice.
Thanks again for your input. |