Does “cash in lieu of dividend” incur any tax consequences in an IRA?
In a (not Roth) IRA, withdrawals are generally already taxed as regular income. So there should be no tax disadvantage to earning payment in lieu of dividends.  It's possible that there is an exception for IRAs but I was unable to find one and I cannot see the reason for one since the dividend tax rate is usually lower than the income tax rate (which is why some company owners elect to receive part of the company profits via dividend rather than all through their salary).
"To keep it simple, I will keep the focus between a Trad IRA and a normal Taxable account (Roth's and 401(k) add more complications that make another problem).  I will also assume, based on the question, that you aren't able to deduct the IRA contributions. Also, a Roth is better in every way than a non-deductible Trad IRA so the ""backdoor Roth"" mentioned in other answers is probably the way to go and this is more of an academic exercise.  Ok, so why bother with the IRA if you're taxed anyway?  Because you aren't taxed as you go! With a normal non-tax-advantaged account you have to pay taxes every year on any realized capital gains and dividends (including fund distributions). Because of the compounding nature of savings, delaying paying taxes is in your best interest.  Simple example:  Taxable Account: IRA Account: Now, this is a very simplified example. If you're more tax-conscious (i.e. more buy-and-holding), you can delay paying some of the long-term cap gains in the taxable account, but any short-term cap gains (including distributions from the underlying funds) will be at your marginal income tax rate.  A few other observations: EDIT: I set up a spreadsheet where each year I deposited $1000 for 35 years. Each year, the balance in the IRA account grows by 5%, but the taxable only by 5%*(1-0.15) = 4.25% due to the effect of taxes. At the end of 35 years, my simulation assumes you pay 15% on all the gains in the IRA, which would likely not be the case, but easier than forecasting through retirement and demonstrates what I'm trying to show. Here's plot showing the balance in the various accounts, the blue is the IRA account, orange the taxable account, and grey is the effective balance of the IRA, after paying taxes on the gains:   And here's a plot of the advantage of the IRA (after paying taxes on the gains), vs the taxable account:  Whether that's worth it to you or anyone depends on some the assumptions in the simulation, especially effective tax rates, and growth rates, as well as any personal issues. Some people may be less likely to raid an IRA account, for example, than a normal account. Conversely, if you have a project coming up, you may need something a bit more liquid than an IRA." Is that basically it? Trading off between withdrawing-anytime vs paying-capital-gain-tax? No. Another significant factor is dividends. In an IRA they incur no immediate tax and can be reinvested. This causes the account value to compound over the years. Historically, this compounding of dividends provides about half of the total return on investments. In a non-IRA account you have to pay taxes each year on all dividends received, whether you reinvest them or not. So outside of an IRA you have a tax drag on both capital gains and dividends. &gt;I could be wrong but you will still get tax at 10%   This isn't true for Roths.  If I put 5k (post tax of course) money into a Roth 401k or a Roth IRA I can withdraw that 5k whenever I want penalty and tax free.  Now lets say that 5k has grown to 7k and I take out all 7k the first 5k is penalty and tax free but the extra 2k is taxed (with the extra 10% penalty added on).  So as long as you don't touch any growth in your roth accounts you can withdraw the principal amount with the same consequences you would experience if you were to take money out of your checking account at your bank.    Also money in and IRA does not have to be invested it could be in a liquid position.    Now a pre tax retirement account doesn't have the same luxury.  If I stick 5k into a traditional IRA and it grows to 7k and I pull that money out the entire ammount gets taxed AND penalized (even the principal amount is subject the 10% penalty).     Now if you do a Roth conversion (pre-tax to post-tax retirment account conversion) the principal ammount (the amount you paid taxes on) is still subject to the 10% penalty for 5 years.  After the 5 years you can withdraw the converted ammount tax and penalty free (well you already paid the taxes) it would just be the growth that is subject to the penalty. "From your description, it seems that you should have $75k of ""basis"" (i.e. after-tax amount) in your Traditional IRA. (As others have mentioned in comments, you might have had to report this in the year it was rolled over. I will assume that you will have figured this out.) Having after-tax amounts in a Traditional IRA is tricky as you usually can't choose to take out only the after-tax portion. Withdrawals as well as conversions to Roth IRA must be ""pro-rata"", which means that the amount of pre-tax and post-tax money in the withdrawal or conversion follows the same proportion as in the IRA overall. So say 7.5% of your Traditional IRA is after-tax, and the other 92.5% is pre-tax, that means any withdrawal will consist of pre-tax and post-tax in those proportions. So e.g. if you withdraw or convert $1000, $75 will be post-tax and $925 will be pre-tax. So any withdrawal or conversion will consist overwhelmingly of pre-tax amounts, which will be taxed, and you may not want that at this time. There is one way to separate the pre-tax and post-tax amounts in a Traditional IRA, but it involves having an active 401(k) (which I doubt you have at this point as you're retired). Some 401(k) plans allow people to rollover funds from Traditional IRA into it. If they allow this, then you can use it to ""siphon"" only pre-tax money from the Traditional IRA, as IRS does not allow rollover of post-tax money into a 401(k). This way you can rollover the entire pre-tax amount of the Traditional IRA into the Traditional 401(k), leaving behind only after-tax money in the Traditional IRA, which you can immediately convert to Roth IRA with no tax." "Bottom line is this: there's no ""short term capital gains tax"" in the US. There's only long term capital gains tax, which is lower than the regular (aka ordinary) tax rates. Short term capital gains are taxed using the ordinary tax rates, depending on your bracket. So if you're in the 25% bracket - your short term gains are taxed at 25%. You're describing two options: For the case #1 you'll pay 25% tax (your marginal rate) + 10% penalty (flat rate), total 35%. For the case #2 you'll pay 25% tax (your marginal rate) + 0% penalty. Total 25%. Thus, by withdrawing from IRA you'll be 10% worse than by realizing capital gains. In addition, if you need $10K - taking it from IRA will make the whole amount taxable. While realizing capital gains from a taxable account will make only the gains taxable, the original investment amount is yours and had been taxed before. So not only there's a 10% difference in the tax rate, there's also a significant difference in the amount being taxed. Thus, withdrawing from IRA is generally not a good idea, and you will never be better off with withdrawing from IRA than with cashing out taxable investments (from tax perspective). That's by design." Yes, it should come out tax free. However you should have reported it  to the IRS at the time (currently it is done on form 8606). If you haven't done it, the IRS may disagree with you on that and require taxes. If you have proper documentation of the contribution, then when you withdraw from your IRA - you use that same form 8606 to calculate the non-taxable portion. Note that you cannot just take $2K out of the 1099-R, the non-taxable portion will be prorated through all of your IRA withdrawals. Also, keep in mind that only the actual after tax portion will be tax-free, the gains will be taxable. I.e.: if you deposited $2K after tax (and nothing else), and they have now grown to $100K - you will only have 2% of your distribution tax free (2k/100K * distributed amount). "Dividends telegraph that management has a longer term focus than just the end of quarter share price.  There is a committment to at least maintain (if not periodically increase) the dividend payout year over year.  Management understands that cutting or pausing dividends will cause dividend investors in market to dump shares driving down the stock price.   Dividends can have preferential tax treatment in some jurisdictions, either for an individual compared to capital gains or compared to the corporation paying taxes themselves.  For example, REITs (real estate investment trusts) are a type of corporation that in order to not pay corporate income tax are required to pay out 95% of income as dividends each year.  These are not the only type, MLP (master limited partnerships) and other ""Partnership"" structures will always have high dividend rates by design. Dividends provide cash flow and trade market volatility for actual cash.  Not every investor needs cash flow, but for certain investors, it reduces the risks of a liquidity crisis, such as in retirement.  The alternative for an investor who seeks to use the sale of shares would be to maintain a sufficient cash reserve for typical market recessions." "If you sell a stock, with no distributions, then your gain is taxable under §1001.  But not all realized gains will be recognized as taxable.  And some gains which are arguably not realized, will be recognized as taxable. The stock is usually a capital asset for investors, who will generate capital gains under §1(h), but dealers, traders, and hedgers will get different treatment.  If you are an investor, and you held the stock for a year or more, then you can get the beneficial capital gain rates (e.g. 20% instead of 39.6%).  If the asset was held short-term, less than a year, then your tax will generally be calculated at the higher ordinary income rates.  There is also the problem of the net investment tax under §1411.  I am eliding many exceptions, qualifications, and permutations of these rules. If you receive a §316 dividend from a stock, then that is §61 income.  Qualified dividends are ordinary income but will generally be taxed at capital gains rates under §1(h)(11).  Distributions in redemption of your stock are usually treated as sales of stock.  Non-dividend distributions (that are not redemptions) will reduce your basis in the stock to zero (no tax due) and past zero will be treated as gain from a sale. If you exchange stock in a tax-free reorganization (i.e. contribute your company stock in exchange for an acquirer's stock), you have what would normally be considered a realized gain on the exchange, but the differential will not be recognized, if done correctly. If you hold your shares and never sell them, but you engage in other dealings (short sales, options, collars, wash sales, etc.) that impact those shares, then you can sometimes be deemed to have recognized gain on shares that were never sold or exchanged. A more fundamental principle of income tax design is that not all realized gains will be recognized.  IRC §1001(c) says that all realized gains are recognized, except as otherwise provided; that ""otherwise"" is substantial and far-ranging."