Up ~400% this year on deep ITM LEAPS (that when I bought were far OTM). hold for LTCG or roll down delta now?
Like alot of you investing in AI/Memory/my beloved Nebius, I had some rough months which turned into explosive growth recently. Most of the positions were opened around April lows and are now up anywhere from \~50% to over 300%.
My portfolio is exclusively LEAPS with expirations from 1/2028-6/2028
Most of the contracts currently have deltas around 0.7–0.9, so they behave almost like leveraged stock positions at this point if I understand that correctly
The dilemma-
If I hold until next April, most positions would qualify for long-term capital gains treatment.
But I’m also aware that I’m sitting on a concentrated, high-beta portfolio after a massive run and could give back a lot if the sector corrects.
My choices-
1.Holding everything until LTCG treatment kicks in
2.Rolling strikes upward to reduce delta while maintaining exposure
3.Trimming some positions now and paying short-term gains
4.Trimming all positions, biting the tax bullet and buying share in order to lock in these gains and play the future a big safer
At what point does risk reduction become more important than optimizing taxes? Portfolio is right around 350k as of today. Thanks all!!