I have the option to pay taxes on the stock right away at the opening price or pay over the next five years at the actual price. I intend on staying with the company for the next five years, but I'm not sure about whether I should gamble on what the price will be. It is a media company, which are traditionally cash cows, but have been losing money as of late. Any advice?

I would go with paying the taxes on the stock right away at the opening price. As long as you can afford the taxes all at once. Otherwise, then take the 5 year option.

It is not an easy answer. You may be able to afford it more now than later. If you retire and the stock grows and taxes are only going to go up you'd be better off paying them now and having them tax free when you are older and don't want to pay higher taxes, possibly. It's your call and if you intend on keeping them it is long term, I's probably pay most of it now and think on the rest for a while and see what happens. Good luck.

You need to provide more information about what you mean that the company "gave" you stock. Normally these things are stock options and the type of option will determine how and when you pay the tax. The option to pay over five years does not sound right. Mu guess is that you have a NQ stock option which you can exercise any time in the next five years. Stock options are a complex issue which should be reviewed by a tax professional before you decide how to proceed.