Treatment of donations of appreciated stock to a IRC §501(c)(7) Social Club?
If cash donations are not deductable, stock contributions aren't either and I believe the same rules apply as for a private party.
If the charity accepts stock, you can avoid the tax on the long term cap gain when you donate it. e.g. I donate $10,000 in value of Apple. I write off $10,000 on my taxes, and benefit with a $2500 refund. If I sold it, I'd have nearly a $1500 tax bill (bought long enough ago, the basis is sub $100).  Any trading along the way, and it's on you. Gains long or short are taxed on you. It's only the final donation that matters here.  Edit - to address Anthony's comment on other answer - I sell my Apple, with a near $10,000 gain (it's really just $9900) and I am taxed $1500. Now I have $8500 cash I donate and get $2125 back in a tax refund. By donating the stock I am ahead nearly $375, and the charity, $1500. Thanks for your reply. I’m not familiar with the term “Held-For-Trading Security”. My securities are generally held as collateral against my shorts. To clarify, I am just trying to track the “money in” and “money out” entries in my account for the shorts I write. The transaction is relatively straight forward, except there is a ton of information attached! In simple terms, for the ticker CSR and short contract CSRUQ8, the relevant entries look something like this: There are no entries for expiries. I need to ensure that funds are available for future margin calls and assignments. The sale side using covered calls is as involved. No. You shorted the stock so you are not a shareholder. If you covered your short, again you are not a shareholder as you statement of account must show. You cannot participate in the net settlement fund. I wouldn't get too caught up with this. Doesn't sound like this is even stock reconciliation, more ensuring the cash you've received for dividends &amp; other corporate actions agrees to your expected entitlements and if not raising claims etc. "One way to possibly disambiguate it from a tip is to receive it outside of your service context.  If there really is a relationship, and they want to show appreciation or help you out financially, the ""gift"" could be given outside of the restaurant.   Otherwise, I agree that it seems like tax evasion.  The purpose of the money was to compensate for services rendered, which is income, not a gift. If it's just a random stranger, then I'd have a hard time arguing that the purpose was pure altruism versus socially-mandated tipping. Why can't I just have my employer just give me a ""gift"" every Christmas instead of a bonus?  Or just reduce by salary by $18k and give me a $1,500 ""gift"" every month?" See I believe that it's pretty in the open. A shell company whose only purpose is to license out some intellectual property to an affiliate company should be easy to spot. A company with 5 employees and a tiny office should not be claiming millions of income that originated in an affiliate company. My point is that these things are not clearly defined in the code and should be, not that they are necessarily being hidden. I've seen at least 5 articles in the last year similar to this one about other large companies, so I wish congress and whoever else would do something about it. This is taxed as ordinary income. See the IRC Sec 988(a)(1). The exclusion you're talking about (the $200) is in the IRC Sec 988(e)(2), but you'll have to read the Treasury Regulations on this section to see if and how it can apply to you. Since you do this regularly and for profit (i.e.: not a personal transaction), I'd argue that it doesn't apply. "As others have mentioned, it's important that there is a fair assessment of the market value of the items being donated.  Joel's point about the government not looking kindly upon overvalued donations also applies in Canada: the CRA doesn't look kindly upon donation schemes such as ""buy-low, donate-high arrangements."" Since nobody has offered up authoritative information for Canada yet, here's something to look at: Excerpts: 3) Gifts in kind of a taxpayer   include capital property, depreciable   property, personal-use property ... [...]   6) The fair market value of a gift in   kind as of the date of the donation   (the date on which beneficial   ownership is transferred from the   donor to the donee) must be determined   before an amount can be recorded on a   receipt for tax purposes. [...]  The   person who determines the fair market   value of the property must be   competent and qualified to evaluate   the particular property being   transferred by way of a gift. Property   of little or only nominal value to the   donor will not qualify as a gift in   kind. Used clothing of little value   would be an example of a   non-qualifying contribution. You will need to find a charity that would both value the books you would be donating and be willing to issue you a receipt for your charitable donation.  Whatever receipt they issue should be in line with fair market value of the goods donated.  Assume your donation receipt will be challenged, and keep both: Finally, reasonable comparables might be prices for similar used goods, not a percentage of new.  Though, if you can't find a price for a particular title in the used market, an estimate consistent with other valuations in the lot would be better than nothing, perhaps." "Can I teach children an invaluable skill for free and provide a website or PayPal link for anyone who appreciates the result of my gift to their child and wishes to gift me money (or maybe they don’t have a child but believe in my revolutionary contribution to the future) as they see fit, up to $10K? Two immediately obvious problems with this strategy: What about when you receive gifts from people who aren't in the US? You have to declare, and pay taxes on, foreign gifts. It seems to me that these may not be gifts because they are given in connection with the service you provided rather than from ""detached and disinterested generosity"" as required to make the gift tax exempt. (See Commisioner v. Duberstein -- gift given to thank associate for a sales lead did not arise from detached generosity. See Stanton v. United States -- gift given in appreciation of services rendered may or may not be a gift for tax purposes. See also Bogardus v. Commissioner -- gifts inspired by past service can be tax exempt.)" You need to be clear about who gets your money: If you pay the existing owner $25K and (s)he gives you half the business, then you now own half of a $50K business an the original owner has an extra $25K in spending cash.  The value of the business has not changed. If you contribute $25 to the company, new equity shares are created.  Shares should be priced correctly, meaning you now own $25K worth of shares in a company worth $75k, so you should have 1/3 of the outstanding shares (counting both old and new shares).  If you get more or less than this, then the transaction has happened in an unfair way. If this is a public company, that would most likely be illegal and the SEC may throw you in jail.  If it was a private company and your friend created enough shares that you own half the company, then (s)he has given you a gift. If you are contributing to the company at a fair price, you would need to contribute $50K in order to end up with half the equity of the new and now more valuable firm. In that case the firm would be worth $100K after your contribution. Bottom line, this is a common and not complex transaction and should end up with a completely fair outcome.  Any unfair situation you can imagine is probably based on false assumptions or a situation where a non-arms-length transaction is transferring wealth contrary to normal rules and procedures. From 26 CFR 1.1012(c)(1)i): ... if a taxpayer sells or transfers shares of stock in a corporation that the taxpayer purchased or acquired on different dates or at different prices and the taxpayer does not adequately identify the lot from which the stock is sold or transferred, the stock sold or transferred is charged against the earliest lot the taxpayer purchased or acquired to determine the basis and holding period of the stock. From 26 CFR 1.1012(c)(3): (i) Where the stock is left in the custody of a broker or other agent, an adequate identification is made if—   (a) At the time of the sale or transfer, the taxpayer specifies to such broker or other agent having custody of the stock the particular stock to be sold or transferred, and ... So if you don't specify, the first share bought (for $100) is the one sold, and you have a capital gain of $800. But you can specify to the broker if you would rather sell the stock bought later (and thus have a lower gain). This can either be done for the individual sale (no later than the settlement date of the trade), or via standing order: 26 CFR 1.1012(c)(8) ... A standing order or instruction for the specific identification of stock is treated as an adequate identification made at the time of sale, transfer, delivery, or distribution. I would point this out to the committee or other entity in charge of handling this at work. They do have a fiduciary responsibility for the participant's money and should take anything reasonable seriously. The flip side to this is 95% of participants -- especially participants under 35 or so -- really pay next to no attention to this stuff. We consider it a victory to get people to pony up the matching contributions. Active participation in investment would blow our minds. Donations need to be with no strings attached. In this case, you make the cash donation, a deduction, and then they pay you, in taxable income. It's a wash. Why not just give them the service for free? Otherwise this is just money going back and forth. In the United States investing towards donation is a great idea because you can donate appreciated securities directly rather than donating cash.  Notice how much this can benefit you: So you get to both (a) donate untaxed money and then (b) deduct that unrealized money from your income total on your tax return. With the above in mind, a good strategy for investing towards this type of donation would be to pick securities that are likely to increase in market value but not likely to produce any other sort of income.  So bonds (which produce lots of interest income), or stocks with dividends, or equity mutual funds (which distribute dividends as capital gains) would all be suboptimal for this purpose. Of course, an even better strategy would be to establish a widely diversified investment portfolio without thought to future donations.  Then, once a year (or whenever), evaluate all your investments and find some where the market value has increased.  Then donate some of those shares.  No special advance planning necessary. Note that your tax consequences could be more complicated depending on your exact situation.  Read the section about Capital Gain Property in IRS Pub. 26 for all the details.  There may be special limits on the amount you can deduct.  Also, donations of short term capital gains are treated much less favorably, so make sure you donate only long term capital gain property. No. There is no asset associated with your short position, so there's nothing to gift. The short position in the stock is purely a liability. When you note that you have a profit in the position, what you mean is that the cash you made when you shorted the stock is more than enough to cover the short position. The only asset in this picture, then, is the cash you made when you entered the short position.