Ok, then if restricted stock, even more sensible to pay taxes by "selling" shares, since your tax would come due on a portion at the grant. Usually the restricted stock I've seen vests in 1/3 increments. If that were the case, then 1/3 would be income immediately. He might also have done an 83(b) where he pays on the stock that isn't vested yet. That would be notable in that people do that when they are confident the stock is going up. If you guys could post what actually happened, we could analyze better. I'm not looking into it given that I generally don't care.