Tax Wins From Investment Losses

You shouldn’t give away a losing stock to charity or to a relative. Instead, sell the stock at a loss. A capital loss can offset a capital gain, eliminating tax on that gain, while excess losses are tax-deductible, up to $3,000 a year. After you sell the stock and get your capital loss, you can give away the cash, if you wish.

On the other hand, you should give away appreciated assets.

If you give appreciated stock to charity, you’ll never pay tax on the gain. As long as the stock was held for more than a year, you’ll get a tax deduction for the full value of the stock.

If you give appreciated stock to a relative, the recipient can sell the shares. If the recipient is in a low tax bracket, any gain on the sale may qualify for a 0 percent tax rate. (Such 0 percent gains are limited if the seller is under 19, or under 24 and a full-time student.)

The 0 percent tax bracket applies if the total holding period (yours and recipient’s) was longer than one year. For shorter holding periods, the low-bracket recipient probably would owe 10 percent or 15 percent on the sale but that’s still a much lower rate than you would have paid by selling the stock yourself.