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I supposed it means, I should sell stocks if I can keep it in the 15% rate? So, I would have to figure in my normal income first? And then I could know what the amount of selling stocks could be?

Well, kind of. As with all things having to do with taxes, the devil is in the details. Since you said "we", I'll assume you are MFJ. For 2021, LT capital gains rates for MFJ are 0% up to $80,800 in taxable capital gains income, 15% for $80,801 - $501,600, and 20% for $501,601+ - except that there is a surtax of 3.8% that starts at $250,000 for MFJ. So, the real LT capital gains tax brackets are:

$0 - $80,800 0%
$80,801 - $250,000 15%
$250,000 - $501,600 18.8%
>$501,600 23.8%

We only have income from social security every year. Let's say $40,000 per year. Our plan was to supplement that by selling stocks every year into our old age. Let's say we are trying to live on $100,000 per year -- $40,000 from SS, and $60,000 from selling stock. Can you apply that 15% "max out" rule to our situation?

Well, given that in 2021 for MFJ who are both over 65, there is a $27,700 standard deduction, it's actually quite likely that you would still be in the 0% LTCG bracket. 85% of your SS income would be taxable, so that's $20,400 of taxable income. But your standard deduction is $27,700, which is $7,300 more than your taxable SS income. So the first $7,300 of capital gains would be covered by the standard deduction, which means you would have to have another $80,800 (in addition to the $7,300) in capital gains to even have any capital gains in the 15% bracket. Since you are only selling $60k of stock, even if that entire amount was a gain because you had a $0 basis, you still wouldn't reach the 15% capital gains bracket.

That said - if you want to leave your stocks to heirs, and you are concerned about the proposal for capital gains to be taxed upon inheritance impacting their inheritance, you could sell enough stock to get your taxable capital gains up to the top of the 0% bracket without having to pay a penny in income taxes. In this example, that would be selling enough stocks to generate $88,100 in capital gains ($80,800 for the 0% capital gains bracket, plus $7,300 that's covered by the standard deduction). Let's say that was $120k in stock. Then you could take the $60k that you don't need for your living expenses, and buy back the stocks that you had sold. That way, you would have $60k in stock with a $60k basis, instead of $60k in stock with a $15,590 basis, and, if the proposal is law by the time you die, your heirs would only have to pay capital gains taxes on the gains above $60k, instead of the gains above $15,590

If you have even more stock that has a low cost basis, and you want to pay the 15% capital gains taxes, instead of your heirs having to pay it when they inherit, you could sell enough stock to generate up to $250k in taxable capital gains.

AJ
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