Ideas on reducing taxes on a huge capital gain

[Anonymous]

Purchase a lot of land and turn it into a conservation easement. Work with a specialized tax professional to do this and do not buy easements from a promoter.

[Anonymous]

The charitable remainder trust was a good idea.

[Anonymous]

Putting the proceeds into an Opportunity Zone Fund would push taxes into the future and reduce them.

[Anonymous]

It's too bad it's happening next year because Trump changed tax laws for charitable giving for 2026. Only the portion of your annual charitable contributions that exceeds 0.5% of your adjusted gross income (AGI) will be deductible.

This “0.5% AGI floor” applies to all itemized charitable gifts, including those made to donor advised funds (DAFs). For example, if your AGI is $1,000,000, only the amount of your charitable giving above $5,000 (0.5% of $1,000,000) will be deductible.

Though, you should still open a donor advised fund and give some of the windfall to charity. Very easy to set up on Fidelity.

[Anonymous]

I have this situation occasionally .

Review your portfolio and tax loss harvest in 2026 (look at each of your positions and sell any where cost is greater than market value)

Hold any recurrent 2025 charitable donations and make double donations in 2026 (especially of appreciated public stock).

Take any anticipated 2026 income items into 2025 if you can.

That's about it.

[Anonymous]

Anonymous wrote:Ask at Bogleheads.org
.

+1

[Anonymous]

Anonymous wrote:Set up a charitable remainder trust. Put the stock in there before the deal closes. You won’t pay taxes on the capital gains and can withdraw income from the trust while you are alive or for a certain term depending on how it’s set up. Whatever is left when you die goes to the charity you designated. Win-win.

Yes. A Charitable Donor Advised Fund (DAF) before the stock is sold generating the capital gain.
https://www.fidelitycharitable.org/?immid=PCD&account=&campaign=230666294&adgroup=176805346921&keyword=fidelity%20daf&gad_source=1&gad_campaignid=230666294&gbraid=0AAAAAD-T465H9sPNztjNpQ2FIWs3W8yr6&gclid=EAIaIQobChMI3-6J1unHkQMVdUr_AR2jKyP_EAAYASAAEgLGtfD_BwE

[Anonymous]

Anonymous wrote:Set up a charitable remainder trust. Put the stock in there before the deal closes. You won’t pay taxes on the capital gains and can withdraw income from the trust while you are alive or for a certain term depending on how it’s set up. Whatever is left when you die goes to the charity you designated. Win-win.

These charitable remainder trusts are not very popular, not sure why. Maybe due to their complexity? OP, I would start by doing a search over at bogleheads.

[Anonymous]

Take losses to offset gains.
Donate stock with big gains. Can donate up to 30% of AGI.

[Anonymous]

Anonymous wrote:

Anonymous wrote:Set up a charitable remainder trust. Put the stock in there before the deal closes. You won’t pay taxes on the capital gains and can withdraw income from the trust while you are alive or for a certain term depending on how it’s set up. Whatever is left when you die goes to the charity you designated. Win-win.

These charitable remainder trusts are not very popular, not sure why. Maybe due to their complexity? OP, I would start by doing a search over at bogleheads.

Op here....yes I've heard the same thing about CRTs. That they are complicated, and the tax reporting can be a major hassle to manage. My gain is multiple 7-figures so it may be worth it.

[Anonymous]

Anonymous wrote:Well, time to dump losers in your portfolio if you have any.

You could do a DAF. Let's say you fund with 100k, and that gives you a major deduction this year, then you can give that away over the next couple years. At least I think that's how it works. I myself have not been in the position of having too much money

This what we did.

[Anonymous]

Anonymous wrote:

Anonymous wrote:If you're making sooo much money off of this, you can afford professional tax advice and don't need to get it from this silly forum.

Yeah, this is just a humble brag.

There’s nothing humble about it. A VBA maybe, but not a humble brag.

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:If you're making sooo much money off of this, you can afford professional tax advice and don't need to get it from this silly forum.

Yeah, this is just a humble brag.

There’s nothing humble about it. A VBA maybe, but not a humble brag.

OP here....I realize this may come across as a humble brag. That was not my intent. It was a genuine question. How is anyone supposed to ask these questions regardless of the numbers involved? If it was a small gain I would have never asked. Besides, based on what I read on this forum, posters on here have a lot of money so who better to ask?

What does VBA mean in the PP?

[Anonymous]

OP - Because of the buyout, you have to take the long term cap gain this year? Normally you choose when to sell and only have the gain in the year you choose.

If you have other assets and this money isn’t immediately required, I would strongly consider putting some of the gain into a DAF. No tax should be owed on the funds, and you get an upfront deduction this year. Double tax benefit. You should run specific numbers by your accountant though.

[Anonymous]

Anonymous wrote:It's too bad it's happening next year because Trump changed tax laws for charitable giving for 2026. Only the portion of your annual charitable contributions that exceeds 0.5% of your adjusted gross income (AGI) will be deductible.

This “0.5% AGI floor” applies to all itemized charitable gifts, including those made to donor advised funds (DAFs). For example, if your AGI is $1,000,000, only the amount of your charitable giving above $5,000 (0.5% of $1,000,000) will be deductible.

Though, you should still open a donor advised fund and give some of the windfall to charity. Very easy to set up on Fidelity.

Trump didn't change any tax laws. Congress did.