Capital gain/loss on selling stock?

Question

If I buy shares of a company multiple times and I sell the shares multiple times, can I take the max difference so I can minimize the gains (or maximize the loss)? Let's say I bought 5 shares of a company each at 20, 18, and 15, and sold 5 shares at 16; can I claim a loss (buy=20,sell=15) instead of gain (buy=15,sell=16). Am I within my rights if I do this for several companies during the year so I maximize the losses instead of showing gains?

Answer 1

You can choose which shares to sell, and instruct your broker to sell the particular shares bought at a particular time or price.  It will all even out in the end anyway, when you have sold all the shares.