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i posted the same thing in the berkshire board and was suggested to post it here:

Here's an interesting situation i thought of. If i have a portfolio of realized short term losses, short term gains, long term losses, and long term gains, I believe ST losses first offset ST gains before offsetting LT gains.

In the US, when short option positions are closed, they are always considered short term losses/gains, regardless of the holding period. But long option positions held over a year are considered long term loss or gains.

Say the S&P is trading at 1400.5, and options trade at a $1 increments. I put on a bull call spread between 1400 and 1401 for about $.5. Now more than a year goes by, and the S&P is now at 1500. The net profit on the position is $.5. But individually, the profit on the long option is going to be at around $100, and the loss is going to be around $99.5. Since the short call option is bearing the loss, it's counted as a short-term loss. The long call has a long term gain. If these were the only two transactions, it would pretty much be a wash ($.5 profit taxed at LT rates).

However, if i were a day trader, and over the course of the prosperous year, I'd racked up a short term gain of $99,500 (same as the loss on the short call). I would then be able to allocate the "short term losses" from the spread to the gains on the day trades, and have the long call taxed at a lower rate. Putting the trade on for that cheap is essentially a free tax hedge. Thoughts, anyone?
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