In the old days, it would be the attorney general—usually an elected attorney general. And if he gets a case into the Supreme Court [pumps his fist], he’s going to argue it himself! Get the press and whatnot. Some of them were just disasters. They were throwing away important points of law, not just for their state, but for the other 49.Who, specifically, do you think he might have been talking about there? I'll tell you who I thought of when I read that: Roger A. Tellinghuisen, the Attorney General for the state of South Dakota, whose argument in South Dakota v. Dole — the key case about Congress's power to attach conditions to spending — threw away an important point of law that could have limited the spending power. For years, when I teach that case, I've urged students to listen to that argument as a lesson in what not to do.
Tellinghuisen was only prepared to talk about the 21st Amendment as a limit on the Spending Power. There's an argument in an amicus brief from the National Conference of State Legislatures that O'Connor pushes Tellinghuisen to use, about how related the condition needs to be to the spending, and Tellinghuisen says he's "not prepared to argue that particular fine point." His case is about a condition that relates to the sale of liquor, so he's all about the amendment that preserves state legislative power in that area, as if all that matters is winning this particular case — which he didn't — and not about the doctrine that will apply to many other cases in the future.
In the 7-to-2 opinion in Dole, written by Chief Justice Rehnquist, we see that the thrown away point in a footnote (boldface added):
Our cases have not required that we define the outer bounds of the "germaneness" or "relatedness" limitation on the imposition of conditions under the spending power. Amici urge that we take this occasion to establish that a condition on federal funds is legitimate only if it relates directly to the purpose of the expenditure to which it is attached. See Brief for National Conference of State Legislatures et al. as Amici Curiae 10. Because petitioner has not sought such a restriction, see Tr. of Oral Arg. 19-21, and because we find any such limitation on conditional federal grants satisfied in this case in any event, we do not address whether conditions less directly related to the particular purpose of the expenditure might be outside the bounds of the spending power.The Court found spending on highway construction sufficiently related to the age at which a person is allowed to buy alcohol. Dissenting, Justice O'Connor said:
When Congress appropriates money to build a highway, it is entitled to insist that the highway be a safe one. But it is not entitled to insist as a condition of the use of highway funds that the State impose or change regulations in other areas of the State's social and economic life because of an attenuated or tangential relationship to highway use or safety. Indeed, if the rule were otherwise, the Congress could effectively regulate almost any area of a State's social, political, or economic life on the theory that use of the interstate transportation system is somehow enhanced.What an astounding missed opportunity to limit conditional spending!