1 result for tag: Smart Investing Tactics


Is “Don’t Die with Capital Loss Carryovers” a Good Rule to Live By?

Question In 2023 "Last-Minute Year-End Tax Strategies for Your Stock Portfolio", you state in Strategy 4, “Don’t die with Loss carryovers.” I ask, “Why not?” Let’s say I have $400,000 in capital loss carryovers, and a stock portfolio worth $2 million with a basis of $1 million. I sell $800,000 worth of stock to generate a $400,000 gain, use my $400,000 carryover loss to avoid taxes, and spend $800,000 to buy back that stock the next day. (The wash sale rule does not apply to gains, so the buyback causes no tax problems.) After this transaction, the loss is gone and I have the following: Result 1. Say I die a day ...