Take long term cap gains in 2021 vs 2022?

^ Seems like I should just sell by end of this year.


1. Uncertainty of Biden increasing long term cap gains rate for high earners. I don’t see why he would let this pass.
2. Penalty for not paying estimated quarterly taxes on a 7 figure gain might be too painful.
 
It wouldn’t be a penalty if you paid estimated taxes for Q4 since the income wasn’t realized until Q4.

if you’re making millions in profits on the trade, maybe you have to watch out for the proposed 2022 $10M+ surcharge bracket for an extra 5% tax rate. If you’re under that, it would only be 23.8% under the current Build Back Bigger bill, but of course that’s still up in the air, may change or may not pass at all.

https://wilkecpa.com/build-back-better-act-bbb/

if it were me, I’d take my chances if I’d be under $10M and delay til next year. Of course, that’s not to say you couldn’t take some chips off the table this year for general risk control / diversification reasons and hedge your tax risks a bit also.

and congrats!
 
^ thank you


I'm no where near the 10M+ surcharge. maybe in a few years. lol


I will probably take some chips off the table this year and defer some taxes until April 2023. It's too bad we don't have a president that would make it 10% across the board. lol.
 
Sell half now and sell half in jan，plow the profit back to 2023 calls.

I am in the same boat and will excise assignments to take some nvda shares next week and buy more nvda calls.
 
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