Desert Dweller .. His risk of loss is negligible when you consider he only paid $6 for an $18 stock today. What is the likelihood this will go down below his strike price?
From an investment perspective, the strike price, since it is a sunk cost, is irrelevant in determining whether or not he has a "loss" after one year. He has an opportunity to guarantee a gain of $12/share now, pay ordinary income tax, and reinvest the net proceeds in an alternative investment other than IDCC, hold that for a year and pay capital gains tax on any gain if he has one. It is that opportunity that needs to be compared against the net result of holding the 15,000 IDCC shares for one year and then paying capital gains tax on any gain if there is one that would determine whether there was a loss by holding on to the shares. There are intangible factors, such as the prudence of diversification, that also should be weighed in the decision.
The point is the stock does not have to fall below the strike price in order for him to lose (i.e. be worse off) given the myriad alternative investment strategies available to him at this point in time as a result of the option exercise. The tax effect is only one factor, albeit an important one, to be weighed in investment decisions such as the one any investor would face in a similar situation. Minimizing taxes is tempting to use in the investment decision making process because it is readily calculated, but it can cause one to leave a lot of investment gains on the table in my experience if it is the primary factor in the decision.
Having said that, like you, it is hard for me to see the stock appreciably below where it is now in a year.
Regards,
Danny