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Not really. But here are a couple of comments that may or may not pertain to your situation.
Basically in order to get long term capital gain treatment you would have to delay passing title to the stock until after your 1 year holding period was met. So, could you sign a contract to make the sale at a later date.
Also, what type of stock are you talking about? Is it a small company? If so is it an S-Corp?
How much the tax bite is will depend on your tax bracket. Are you in a high tax bracket? The difference between the long & short term capital gain rate may not be that great/
What would putting the stock in a trust accomplish?
The trust, if it were irrevocable, would have a shorter holding period that you. If it was revocable, it would be taxed to you anyway.
Less than a year is short term.
The same as ordinary income; it would depend upon the amount of the gain. How much is the gain & I can tell you. But the trust would have to be irrevocable.
What kind of company are you talking about? Is it a public company or is a public company taking it over?
Is the stock you hold restricted?
Can you gift any of the stock to family members to spread the gain to children (for example) who would be in a lower tax bracket than you are?
Right, but are you restricted from transferring the stock to someone else or do you have to offer it back to the company first?
Is it realistic for you to give up access to the 400+ K by putting it into a irrevocable trust?
Are you sure that you will receive cash or is it possible you would (or could) receive stock of the acquiring (public) company. That could be tax free & then your holding period of the new stock would include the holding period of the existing stock too,
No. If the trust was revocable, you would be taxed on the sale whether or not you received the proceeds or the proceeds stayed in the trust. It's the control factor that would govern.
So, are you the only one with a short-term holding period?
The holding periods are determined separately.
If you were allowed to transfer any of the stock to a trust, you could set up a revocable trust with multiple beneficiaries who would all be taxed at their individual tax rates on the sale of the stock, including you for whatever interest you had in the trust.
You would have to file gift tax returns for the value of the stock at the time you contributed it to the trust for the beneficiaries; but you wouldn't have any tax to pay until your lifetime transfers exceeded $5,250,000.
or 5,125,000. I forget which for 2013.
Yes. As I stated about the tax would be paid by the beneficiaries of the trust (including you), but I presume that their tax brackets wouldn't all be as high as yours. Of course, they would either have to leave the money in the trust and they would be entitled to their share of the trust assets; but there would be no restriction as to what they could do with their share of the cash after the taxes were paid.
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