I try to maximize LEAP use in my 401K but I do have some in a taxable account. I'd like to understand what's my best strategy to deleverage. Especially relevant in a short squeeze scenario of course but applies to any. All of my LEAPS at this point are long term holdings. Some are 2019, some 2020. My understanding is that the most optimal strategy from the tax perspective, if I simply want to keep funds in TSLA or derivatives and reduce leverage, is: 1. Outright sell LEAPs expiring in 2020 to get the time value back, take the tax hit 2. Do the math on 2019's to see if it's better to sell and take the tax hit and use proceeds to buy stock, or use proceeds from #1 to exercise those options and avoid paying taxes but missing out on time value. Does that sound about right?