What does it mean to be “offset against taxable gains”?
"Offset against taxable gains means that the amount - $25 million in this case - can be used to reduce another sum that the company would otherwise have to pay tax on. Suppose the company had made a profit of $100 million on some other investments. At some point, they are likely to have to pay corporation tax on that amount before being able to distribute it as a cash dividend to shareholders. However if they can offset the $25 million, then they will only have to pay tax on $75 million. This is quite normal as you usually only pay tax on the aggregate of your gains and losses. If corporation tax is about 32% that would explain the claimed saving of approximately $8 million. It sounds like the Plaintiffs want the stock to be sold on the market to get that tax saving. Presumably they believe that distributing it directly would not have the same effect because of the way the tax rules work. I don't know if the Plaintiffs are right or not, but if they are the difference would probably come about due to the stock being treated as a ""realized loss"" in the case where they sell it but not in the case where they distribute it. It's also possible - though this is all very speculative - that if the loss isn't realised when they distribute it directly, then the ""cost basis"" of the shareholders would be the price the company originally paid for the stock, rather than the value at the time they receive it. That in turn could mean a tax advantage for the shareholders."
I have a little experience with this.  My home state of Wisconsin was on this list until 2011. The thing to remember is that these states simply do not recognize the HSA.  What this means is that there are no state income tax advantages to the account, and no state tax penalties, either. Here are the implications: When you invest in a taxable account, your broker in many cases keeps track of cost basis for you.  However, when you invest inside an HSA, your HSA custodian will generally not keep track of any of this, because it is not normally needed.  Therefore, you need to keep track of any cost basis yourself, and when you sell, calculate the capital gain or loss on your state return. In my opinion, the HSA is a good deal even if your state does not recognize it.  The tax-free savings/investing is a great deal, even if only on your Federal taxes.  The state return will be a little more complicated, but the savings you get on your federal return are worth it. In my situation, our family spends the money in the HSA on medical expenses fast enough that we don't invest it in anything other than an interest-bearing savings account.  Therefore, we didn't have to worry about capital gains inside our HSA, and only had to add contributions and earnings to our state income.  I am very glad that our state now recognizes the HSA. The cap loss can be used to offset future gains or $3000/yr of ordinary income. (I just used up the last of mine from the dot com bubble.) I hope you have future gains that let you use this up quickly.  The IRS debt is separate, and I don't imagine they'll let you use any of the loss to offset it. As always, it can't hurt to ask. Their normal payment plans are for 5 years. $40k/yr is a lot.  Edit - The IRS does negotiate. I recall, from the dot-com bubble, instances where someone exercised stock grants, but kept the shares. Now, they had a $1M gain, but after year end, the stock crashed. They owed tax on that gain, but the loss was in the next tax year, with nothing to offset. These people were 'regular' guys and gals, no background in finance. I understand the IRS looked at these people and made some exceptions. What might make more sense is to 'capture' your losses.  Sell out the funds you have, move into something else that is different enough that the IRS won't consider it a wash sale, and you can then use those losses to offset gains (you can even carry them forward)   You would still be in the market, just having made a sort of 'sideways move'.  A month or two later (once you are clear of wash sale rules) you could shift back to your original choices.  (this answer presumes you are in the US, or somewhere that lets you use losses to offset gains) "If you only have to pay 23k federal taxes on 100k, that means you are in the long term capital gains tax rate, which is the lower of the tax rates available. First you get your federal income tax marginal tax rate, and then find the matching long term capital gains tax rate. For example, if your marginal federal income tax rate is 28%, your capital gains tax rate would be 15%. Or rather, if the amount of the gain would put you in the 28% rate, then your long term capital gains tax rate is 15%. You can reduce that by having more losses. If you have anything else invested anywhere that is taking a loss, then you can sell that this year and it will offset the other gains you have realized. The only note is that your losses have to be long term capital losses too. Tax loss harvesting takes this to an extreme where you sell something at a loss to lock in the tax loss, but you didn't really want to get rid of that investment, so then you buy a nearly identical investment. ie. if you owned shares of ""Direxion Tech Sector ETF"" and it was at a loss, you would sell that and then immediately buy ""ProShares Tech Sector ETF"", the competing product that does the exact same thing. Then there is charity. This still requires spending money and you not having it any longer. If you feel that a cause can use the money more directly than the US government, you can donate an appreciated asset to the charity - not report a gain and also take a charitable deduction." A Section 1256 contract is any: Non-equity options include debt options, commodity futures options, currency options, and broad-based stock index options. A broad-based stock index is based upon the value of a group of diversified stocks or securities (such as the Standard and Poor's 500 index). 60% of the capital gain or loss from Section 1256 Contracts is deemed to be long-term capital gain or loss and 40% is deemed to be short-term capital gain or loss. What this means is a more favorable tax treatment of 60% of your gains. http://www.tradelogsoftware.com/tax-topics/futures/ It's a really wierd rule (arbitraty 60% designation, so broad, etc), but section 1256 contracts get preferential tax treatment and that's what Buffett's talking about. Capital losses from the sale of stocks can be used to offset capital gains from the sale of a house, assuming that house was a rental property the whole time.  If it was your principal residence, the capital gains are not taxed.  If you used it as both a rental and a principal residence, then it gets more complicated: http://www.cra-arc.gc.ca/tx/ndvdls/tpcs/ncm-tx/rtrn/cmpltng/rprtng-ncm/lns101-170/127/rsdnc/menu-eng.html More likely I miswrote.  Yes, we're talking about capital gains.  But who, outside of the moneyed elite, have enough capital gains to incur substantial taxes?  Many don't and never will despite how hard they work or how productive they are.  Also, doesn't taxing income more than capital gains discourage production?  I always hear how high capital gains tax discourages investment and growth. It appears to me that the tax code gives significant advantages to being a corporation as opposed to being a person due to the relative ease of legal tax avoidance.   As an individual, avoiding taxes is much harder than it is for a corporation.   I mean, why can't I claim my deficit last year as an operating loss and use it to offset my taxes?  I mean suppose I had to borrow money to afford food, that's pretty vital to my business (staying alive) operations. Why can't I offset my income with my borrowing like a corporation can?