Probably the wrong forum, sorry about that. Problem: This year I have 19,000 of stock losses from ABC. Losses that would count for taxes as I have closed this position (Bought and sold). I also I have 13,000 of unrealized gains. I bought CBA and I have not sold yet. When I do sell CBA I'll owe taxes on this money. I thought that I would hold onto CBA and use the money that I would have otherwise had to pay taxes on if I had sold it as more leverage. However, here is the problem. Stocks losses can be deducted up to your stock gains + 3,000 off your income. If you have more deductions you have to carry it over the years hence 2nd year I'll deduct another 3,000, 3rd year same, .... until I add up to 19,000. However, for the next few years I only plan on making about 40,000 to 50,000 due to poker being over. Currently my last tax dollar is taxed @ 35% federal and 5.04% state. If poker would still be around and I'd be making this, I would not sell CBA and take the 40.04% write off each year, however I only plan on making 40,000 to 50,000 where the write off is going to be much much less (% wise). Which is the better option (1) Do not sell CBA and take the write off each year keeping in my time value of money and that I'll be at the 15-20% bracket and paying taxes on 12,000 for CBA when I sell it or... (2) Selling CBA. Pay the taxes on CBA (actually deducting it from the loss of ABC) and re buy CBA again Also, I plan to keep CBA for a while