Lawrence Lessigis convinced that he lost Eldred v. Ashcroft in the oral arguments:
When the chief justice called me to begin my argument, I began where I intended to stay: on the question of the limits on Congress’s power. This was a case about enumerated powers, I said, and whether those enumerated powers had any limit.
O’Connor stopped me within one minute of my opening. The history was bothering her:
Congress has extended the term so often through the years, and if you are right, don't we run the risk of upsetting previous extensions of time? I mean, this seems to be a practice that began with the very first act.
She was quite willing to concede “that this flies directly in the face of what the framers had in mind.” But my response again and again was to emphasize limits on Congress’s power:
Well, if it flies in the face of what the framers had in mind, then the question is, Is there a way of interpreting their words that gives effect to what they had in mind? And the answer is yes.
There were two points in this argument when I should have seen where the court was going. The first was a question by Kennedy, who observed,
Well, I suppose implicit in the argument that the '76 act, too, should have been declared void, and that we might leave it alone because of the disruption, is that for all these years the act has impeded progress in science and the useful arts. I just don't see any empirical evidence for that.
Here follows my clear mistake. Like a professor correcting a student, I answered,
Justice, we are not making an empirical claim at all. Nothing in our copyright clause claim hangs upon the empirical assertion about impeding progress. Our only argument is, this is a structural limit necessary to assure that what would be an effectively perpetual term not be permitted under the copyright laws.
That was a correct answer, but it wasn’t the right answer. The right answer was to say that there was an obvious and profound harm. Any number of briefs had been written about it. Kennedy wanted to hear it. And here was where Don Ayer’s advice should have mattered. This was a softball; my answer was a swing and a miss.