I had this situation back in the dot com crash. I sold 2000 options in June. The following April I had to sell 15,000 to pay the taxes on the 2000. The follo

I had this situation back in the dot com crash. I sold 2000 options in June. The following April I had to sell 15,000 to pay the taxes on the 2000. The following April I had to sell another 10,000 to pay the taxes on the 15,000. If I had sold 20,000 instead of 2,000 and used that to pay taxes, I would have been in a far better financial situation. Fortunately, I never went into the red, but I know people who did.