I just finished reading Williams' brief in U.S. v. Williams, and it's pretty shoddy.

The brief has many substantive and structural problems: For instance, it keeps arguing that the child pornography pandering law is overbroad because the law lacks the proper mental state requirements; but the government argues, quite plausibly, that the law does include those mental state requirements, and the brief never adequately responds to the government's argument. More broadly, the brief spends a lot of time repeating platitudes that are surely familiar to the Justices and law clerks, and far too little time responding concretely to the government's concrete legal arguments.

But for now, let me just point to the less important but more obvious problems with the brief — the remarkably shoddy writing. I quoted the opening sentence of Part I of the Argument below, but here are some more examples:

The Section, as currently drafted, while appearing to one person to constitute an offer or solicitation to sell, buy or barter contraband --- whether true or false --- can appear to another person (listening to the same words of the speaker) to be an offer or solicitation to sell, buy, or barter something totally lawful and therefore, protected by the First Amendment....

Subsections (i) and (ii) of the PROTECT Act pandering provision capture what is clearly child pornography both before and after Free Speech Coalition was decided whether involving actual or virtual child pornography....

However, the Section, as written, addresses not only liability to the offered or solicited material but rather to the ideas and images communicated to the viewer by the representation of what those materials constitute, the First Amendment is necessarily implicated....

And while this Court tries "not to nullify more of a legislator's work than is necessary, ... " (Reagan v. Timer, Inc., 468 U.S. 641, 652 (1984)), when a statute is as overbroad and vague as the Section, and particularly where it affects First Amendment freedom, the more frustrating remedy is to simply let Congress re-write the statute rather than risk speech freedoms of millions of people across the country every day and then burden witnesses, law enforcement, prosecutors, judges, juries and higher courts with trying to sort out the mess created by the Section on a case by case basis....

There are many other such passages. As an editing exercise for a legal writing class, this brief would be excellent. As a brief in the Supreme Court, not so much.