As previously stated, don't let taxes cause to you make bad investment decisions, but this doesn't mean that you shouldn't consider taxes in the timing of sales. 1.) Would you buy the stock again? The answer appears to be no. If you are planning on getting rid of the stock, then selling it before the end of year or they go into bankruptcy is reasonable. Once a company enters bankruptcy, there can be an extended time before the stock becomes officially worthless or the company emerges from bankruptcy. Some just fade away, making it very difficult to determine the date that the stock became worthless. 2.) Do you have realized capital gains? Capital losses first offset capital gains, and then each year $3,000 can be taken against regular income. Any unused loss is carried forward to the next tax year. As the end of year appoaches, shaggy dogs can start to look more shaggy. As investors sell stocks that are down to cover gains in others, it can further depress the value of the shares. As with all stock sales, it is your best guess as to when is the best time to sell.
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