I would just hold on to the winners, let them (hopefully) become long term gains which will be taxed at a lower rate sometime in the future, if you don't need the money now.You can take up to a $3000 capital loss and deduct it against your other income. If your loss is more than $3000, you might consider selling only a portion of your position. Otherwise you can carry over the excess over 3,000 for use in future years.If your primary motivation is tax reduction and not investment timing, you will want to reinvest your proceeds. You can't reinvest in the same stock unless you wait 30 days, because of the wash sale rules, but to make the move as investment neutral as possible, buy another similar company in the same industry. Often when an industry is out of favor, your company isn't the only one down. For example, in the banking industry, take a loss on Bank One and use the proceeds to buy First Union, or vice versa. These banks are both down for the year, have a high yield, similar P/E ratios and market capitalizations. A trade such as this will minimize the risk of making a bad investment decision as a result of a good tax decision.
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