WWYD with this taxable stock holding?

disneysteve

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When my cousin died in May 2021 I inherited 3 individual stocks from him in a taxable account. What I probably should have done was sold them right away at the stepped up basis and invested the proceeds. That never happened. Now it's 4+ years later and there are gains to deal with if I sell them.

Stock #1: Cost basis $10,600. Current value $21,700.
Stock #2: Cost basis $102,400. Current value $150,500.
Stock #3: Cost basis $43,100. Current value $399,200.
(All numbers are rounded off.)

Selling #1 wouldn't be terrible as far as CG is concerned. #2 would be a bigger hit. But #3 is the real question sitting on a $356,000 gain. On one hand, not selling it upon inheritance turned out quite well. On the other hand, now what?

Do I start liquidating it gradually over the next few years to trim back the holding but not get hammered with taxes in any one year? We have been getting ACA subsidies but that may or may not continue depending on what Congress ends up doing whenever they go back to work. My wife turns 62 in December; I turn 62 next August. So Medicare starts in December 2028 for her and August 2029 for me so there's IRMAA calculations to start thinking about with our 2026 MAGI.

Do I just hang on and hope it continues to do well and worry about it later, or never and let our daughter inherit it?

No, we don't need those specific dollars for anything. However #3 is creeping up on being 10% of our portfolio which I'm not comfortable with.
 
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Did you see this? Is it applicable?
 
Wow, those are amazing gains from the stepped up basis in just over 4 years!
First world problem for sure but now we need to figure out what to do about it. If it was in an IRA I’d sell at least some of it for sure. In a taxable account it’s not so easy.
 
Did you see this? Is it applicable?
I saw that thread but only skimmed it. I’ll have to read it in more detail.
 
Bonus money that may or may not move the needle for you :)

If they don't fit with your investment strategy, sell, take the gains and pay the taxes.

Be glad you were hit with a lucky stick and grateful you can blow up your ACA subsidies and still have plenty left.
 
Nice windfall. I guess I don't see why it would be difficult to sell of relatively small portions of your windfall and pay the taxes. Just make it fit with the rest of your income to keep within a given tax bracket and avoid any other pitfalls.

I understand that there is a dilemma here, tax wise, but I'm sure you can manage it with a pencil and the back of an envelope - maybe TurboTax.
 
Sell gradually as long as you can pay 15% or less in federal income tax on the gain and not mess up your ACA subsidies too much or exceed the IRRMA threshold.
 
You obviously do not actually view these stocks as investment worthy and were only willing to hold onto when you thought the amounts were trivial. Sell them immediately, pay the 20% capital gains tax as there is no investment reason to hold these. Had you invested these the "intelligent" way 100% in VTI when you had the stepped up value today would be $298,439 with $143,000 of imbedded capital gains instead you will have a full taxed $486,540 after paying $84,860 in taxes.

Based on your apparent investment strategy I find it difficult for the logic to hold an investment in individual stocks when you do not actually have a strategy for them other than they are valuable.
 
Turn off DRIP if DRIP is on

Choices:
Donate to DAF
Gift to DD now, especially if she is in 0% LTCG tax rate
Sell and pay taxes
Let DD inherit them

None of the choices are that bad. Obviously, you can do a combination of them and spread them out over multiple years.

If you don't currently itemize and want to go the DAF route, you may want to bunch your deductions to get the most bang for your buck.
 
I have 3 individual stocks with large capital gains that are left over from my days when I thought I could pick individual stocks. I've been "stuck" with them for years now as I've also been managing my income to help with ACA subsidies. Collectively, they are now about 15% of my holdings. I'm 63 1/2 years old now and will continue to let them ride until I finish the tax year where I turn 65. Once on Medicare, my plan is to slowly start selling these stocks in the lower capital gains brackets as much as I can without getting into IRMAA. That income will likely be what I use to pay for my expenses at that point. I'm not quite sure how it work out, but I'm keeping my fingers crossed I can gradually unwind from the 3 stocks.
 
I'd like to know the name of Stock #3 .

Just so I know what I missed :)
I'm surprised someone didn't ask sooner.

#3 is CEG which was a spin off from EXC (#2). #1 is BK. My cousin used to work for them.
 
Number 3 is an excellent candidate for charitable giving or legacy so your heirs can get that same step-up advantage.
 
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