Well my thought was that instead of selling your LEAPS to book short term gain, if you need money or book some profit, you can sell higher strike calls with same expiration to get some money. Since you have not booked any profit, you don't pay taxes. This conversation belongs to advance options thread and do read it to understand more about options before making a move.
Feel free to take this to the advanced options trading thread, but what pGo says is only half true:
If you have LEAPS and want to take profits without paying gains, then yes you can sell higher strike calls against those LEAPS to collect cash and create a spread, but:
1. If you sell a deep ITM call against those LEAPS then you will be taxed on those gains anyway, since IRS considers selling deep ITM covered calls (I think it applies against underlying stock position as well, but can't remember for sure). Deep ITM is considered anything more than 1 strike ITM, but nothing is set in stone and is open to interpretation by the IRS.
E.g. you have J16 $200 LEAPS and want to sell a covered call, you can do so and not pay taxes as long as it isn't Deep ITM. TSLA is at $255.36 right now, so if you sell the $255 or above then you don't pay taxes. $250 might be okay, but is open to interpretation. $245 might not be okay and you will be hit with a tax bill.
2. If you sell a call against your LEAPS then you may lose LTCG (long term capital gains) benefit of LEAPS if short call is held for less than 12 months.
E.g. If you have J16 $200 LEAPS and sell a J16 $260 LEAPS against it, then you are okay. No tax paid today, since it isn't deep ITM. If you hold this delayed bull call spread for more than 12 months, then you can cash out and pay LTCG on entire spread.
But if you Had that $200 LEAPS for 6 months now, and you sell a J16 $260 against it today, then the clock resets and you need to hold another 12 months to get LTCG treatment. So if you sell 8 months later, you are forgoing LTCG even though you held the long LEAPS 14 months, and will have to pay STCG tax instead on gain.
Alternatively, if you have J15 LEAPS that you held for 14 months now; you can sell them today and claim LTCG. But if you sell a $260 J15 against it today to create a delayed construct bull call spread, then your holding period resets and you are screwed. You will then incur STCG on all of this.
In the end the tax code is extremely complex. I have done a lot of research on this topic and this is how I understand it. I may have misinterpreted IRS language, which is extremely easy to do, so please consult your tax advisor; although I guarantee you that he will not know the correct answer either...
Note: I pasted this post into Advanced options trading strategies thread as well, so we can carry on discussion there if necessary.
