Can Tax Loss Harvesting Carry Over Year to Year?

Hey Mark,

The extent of your knowledge on these subjects is amazing. I don’t know about the other guy though.

In crypto I did so many transactions on so many coins and exchanges that throughout the years of being “in the game” most of my coins have gone up so much that last year buying, selling, and trading led to a ton of gains without setting any profits on the side stupidly thinking that the gains will continue to rise and we’ll use that to pay any taxes. On 2020 taxes I received a refund so I had no idea if I owed anything for 2021 so I did not put up any money when filing an extension this year.

This month we just finished filing our taxes and we owe a whopping $130,000 plus fees and interest.

Boy oh boy were we in shock as this year everything has tanked and we would have to virtually sell all our crypto assets to pay it off. This is very irritating because I worked so hard for so many years to get to this point.

Question:
Can I utilize Tax Loss Harvesting (Wash Sell) for 2022 taxes while crypto is down (or stocks, which I know it’s a month between repurchase for stocks. A minute between crypto to repurchase [side question: is this still allowed?] and have this offset my outstandingly large tax bill of larger than $130,000. Example, doing it this year showing a loss of let’s say $100,000 would drop my bill from $130,000 down to $100,000 (I cross my fingers :crossed_fingers:t4:as I have a huge feeling that the losses will only be put towards 2022 passive profits and losses and not prior years tax burdens)

If not, How should I play this out to be the most advantageous in this situation?

Thank you and sorry for it being so long!

P.S. Just kidding! Mat is phenomenal too.