The Quotable Judge Posner 197-201 (Robert F. Blomquist (Valparaiso), ed.) (SUNY Press, 2010):

1. “The parents between them own 75 percent of the corporation’s stock, so that quite apart from their parental control over the minor children who are the other shareholders, they legally control the corporation and could if they had wanted have directed them to pay them just their pro rata share of the dividend distribution. They did not, and now repented of their decision and want the Internal Revenue Service to undo it from them. This is an unusual request with no precedent that we have been able to find. The taxpayer, having made his bed, must lie in it.” Johnson v. Commissioner, 720 F.2d 963, 964 (7th Cir. 1983).
2. “The problem is that many expenses are simultaneously business expenses in the sense that they conduce to the production of business income and personal expenses in the sense that they raise personal welfare. This is plain enough with regard to lunch; most people would eat lunch even if they didn’t work. Commuting may seem a pure business expense, but is not; it reflects the choice of where to live, as well as where to work. Read literally, section 262 would make irrelevant whether a business expense is also a personal expense; so long as it is ordinary and necessary in the taxpayer’s business, thus bringing section 162(a) into play, an expense is (the statute seems to say) deductible from his income tax. But the statute has not been read literally. There is a natural reluctance, most clearly manifested in the regulation disallowing deduction of the expense of commuting, to lighten the tax burden of people who have the good fortune to interweave work with consumption. To allow a deduction for commuting would confer a windfall on people who live in the suburbs and commute to work in the cities; to allow a deduction for all business-related meals would confer a windfall on people who can arrange their work schedules so they do some of their work at lunch.” Moss v. Commissioner, 758 F.2d 211, 212 (7th Cir. 1985).
3. “Although an argument can thus be made for disallowing any deduction for busi¬ness meals, on the theory that people have to eat whether they work or not, the result would be excessive taxation of people who spend more money on business meals because they are business meals than they would spend on their meals if they were not working. Suppose a theatrical agent takes his clients out to lunch at the expensive restaurants that the clients demand. Of course he can deduct the expense of their meals, from which he derives no pleasure or sustenance, but can he also deduct the expense of his own? He can, because he cannot eat more cheaply; he cannot munch surreptitiously on a peanut butter and jelly sandwich brought from home while his client is wolfing down tournedos Rossini followed by souffle au grand marnier. No doubt our theatrical agent, unless concerned for his longevity, derives personal utility from his fancy meal, but probably less than the price of a meal. He would not pay for it if it were not for the business benefit; he would get more value from using the same money to buy something else; hence the meal confers on him less utility than the cash equivalent would. The law would require him to pay tax on the fair value of the meal to him; this would be (were it not for costs of administration) the economically correct solution.” Id. at 212-13.
4. “There is no limit to the subtleties that lawyers steeped in the economics of income and wealth could excogitate in defense of this or that inclusion or exclusion.” In re Wagner, 808 F.2d 542, 548 (7th Cir. 1986).
5. “Section 6672 casts the net of liability over ‘any person required to collect, truthfully account for, and pay over’ withholding taxes—any ‘responsible person’ in tax jargon, not just the employer and not just the most responsible person. Wright v. United States, 809 F.2d 425, 427 (7th Cir. 1987).
6. “Concretely we hold that the “responsible person” is liable if he (1) clearly ought to have known that (2) there was a grave risk that withholding taxes were not being paid and if (3) he was in a position to find out for certain very easily. It would have been easy for Wright to look at [the company’s] books. He had a right to look at them and the know-how to understand them…. Every time he signed a check he should have wondered, in light of [the company’s] history of delinquency, the company’s modest scale, and the lack of improvement in its fortunes, whether history was repeating itself and he was paying creditors money that belonged to the government. Id. at 427-28.
7. “No writing, however detailed, can eliminate all questions of interpretation; the existence of a large body of case law arising from disputes over the meaning of the Internal Revenue Code shows this.” Tyson v. International Brotherhood of Teamsters, Local 710 Pension Fund, 811 F.2d 1145, 1149 (7th. Cir. 1987).
8. “[F]orm is terribly important in tax law. Forms provide a framework for confident planning. Estate of Boyd v. Commissioner, 819 F2d 170, 172 (7th Cir. 1987).
9. “The Railroad Retirement Act [26 U.S.C. §§ 3201 et seq.], passed in 1937, is to the railroad industry what the Social Security Act is to other industries: the imposition of an employment or payroll tax on both the employer and the employee, with the proceeds used to pay pensions and other benefits. Standard Office Building Corp. & Santa Fe Land Improvement Co. v. United States, 819 F.2d 1371, 1372 (7th Cir. 1987).
10. “Economic theory suggests that most of the burden of a payroll tax is borne by the employees, in the form of lower wages or fewer employed, rather than by the employer—and this regardless of whether the tax is nominally on the employer or the employee. An employer willing to pay $20 an hour for a worker does not care whether he pays the worker the whole $20 or pays $18 to the worker and $2 to the government, but he will not pay the worker $20 if he must pay $2 to the government and the worker is worth only $20 to him.” Id.
11. “If you own the Mona Lisa and paint (indelibly) a mustache on it before giving the painting to your child, with the result that its value is greatly reduced, still your gift tax will be computed at the reduced value.” Citizens Bank & Trust Co. v. Commissioner, 839 F.2d 1249, 1254-55 (7th Cir. 1988).
12. “There is no rule against taking advantage of opportunities created by Congress or the Treasury Department for beating taxes.” Yosha v. Commissioner, 861 F.2d 494, 497 (7th Cir. 1988).
13. “Many transactions are largely or even entirely motivated by the desire to obtain a tax advantage. But there is a doctrine that a transaction utterly devoid of economic substance will not be allowed to confer such an advantage.” Id.
14. “Expenses incurred solely to produce income should in principle be deductible from income tax because otherwise the taxpayer would be taxed on his gross revenue, not on his income. The difficulty is that often expenses have a dual purpose—they produce income but they are also a form of consumption, producing not income but utility. . . . The specific abuse to which the home office deduction conduced, before the deduction was narrowed in the current law, was that an employee could by transferring some of his work from the place of his employment to his home deduct from income tax a portion of his living expenses–expenses he would have incurred even if he had not been working at all.” Caldwallader v. Commissioner, 919 F.2d 1273, 1275 (7th Cir. 1990).
15. “Railroads have long been attractive targets for state and local taxing authorities: so many railroad assets are at one specialized to railroading and physically immobile that it is very difficult for railroads to escape heavy taxation by transferring the assets to another industry or location; in other words, the ‘exit’ option for limiting political exploitation is denied them. Burlington Northern Railroad Co. v. City of Superior, Wisconsin, 932 F.2d 1185, 1186 (7th Cir. 1991).
16. “It is a long time since American government operated on the principle that government governs best which governs least. Much modern legislation involves targeting government largesse on politically influential groups and the burdens of government on politically impotent ones. Not infrequently the legislation benefits a tiny handful of individuals or firms or even a single firm—the latter is especially common in tax legislation…. ” Central States Southeast & Southwest Areas Pension Fund v. Lady Baltimore Foods, Inc., 960 F.2d 1339, 1342 (7th Cir. 1992).
17. “There is no basis in law, public policy, natural justice, or any other source of norms for .. so artificial an entitlement as the foreign tax credit.” Continental Illinois Corp. v. Commissioner, 998 .F.2d 513, 517 (7th Cir. 1993).
18. “Not every receipt is income. A deposit, for example, is not. … The recipi¬ent-bank, landlord, electric utility, whatever—holds the money under obligation (albeit defeasible) to return it. On the other hand income does not cease to be such because there is some likelihood that the recipient may have to give it back. For there is always some likelihood of that. The income that a seller receives from the sale of goods may have to be refunded because the goods were defective or the seller broke the contract of sale in some other way—and some sellers offer to take goods back and refund the buyer’s money with no questions asked. A seller who offers a discount for customers who buy a minimum amount in the course of a year receives income from those customers subject to a contingent obligation to repay a portion to those customers who reach the minimum. Such contingencies have never been thought to entitle a seller to delay recognizing income until the time during which the contingencies could have materialized is past.” Id. at 521.
19. “The government receives tens of millions of tax returns and if taxpayers start embellishing the jurat [the signature certification] the staggering task of processing all these returns may become entirely unmanageable.” Sloan v. Commissioner, 53 F.3d 799, 800 (7th Cir. 1995).
20. “You can’t resist the payment of taxes on the ground that someone else isn’t being made to pay his fair share.” Buchanan v. United States, 87 F.3d 197, 202 (7th Cir. 1996).
21. “But people who are under investigation and represented by a lawyer have the same duty as anyone else to file tax returns. They should not be permitted, by using a lawyer in lieu of another forth of tax preparer, to obtain greater confidentiality than other taxpayers.” United States v. Frederick, 182 F.3d 496, 501 (7th Cir. 1999).
22. “It is desirable that rules of taxation be simple and that they be neutral, in the sense of not influencing business judgments except when the purpose of a particular provision of tax law is to influence behavior. . . .” Nahey v. Commissioner, 196 F.3d 866, 869 (7th Cir. 1999).