The Supreme Court has long struggled to decide just how far the First Amendment allows government to go in enlisting groups and individuals to espouse its policy preferences. An appeals judge recently wrote that this area of the law is "messy and unsettled."

The justices on Monday appeared no closer than before to tidying things up.

The court heard arguments in U.S. Agency for International Development v. Alliance for Open Society International, a challenge to a 2003 law that funds international programs to fight AIDS and HIV overseas, and requires recipients to adopt a policy "explicitly opposing prostitution and sex trafficking." The requirement affects not only the specific programs funded under the law, but also the entire recipient organization, including privately funded operations.

Groups fighting the law say that adopting the required policies could offend host nations and high-risk populations they seek to work with, and could thwart certain anti-AIDS strategies, such as advocating lesser punishment for prostitutes. Lower courts have generally agreed. The U.S. Court of Appeals for the 2nd Circuit said the forced policy pledge "falls well beyond what the Supreme Court … [has] upheld as permissible conditions on the receipt of government funds," because "it does not merely restrict recipients from engaging in certain expression … but pushes considerably further and mandates that recipients affirmatively say something."

Several Supreme Court judges appeared just as skeptical of the law when Deputy Solicitor General Sri Srinivasan rose to defend it. Chief Justice John Roberts Jr. referred to the provision as a "loyalty oath" requirement that could force organizations to espouse government positions on issues ranging from recycling to apartheid. "There have to be some limitations," Roberts said.

Justice Samuel Alito Jr. seemed even more disturbed by the law, stating that the court had never permitted Congress to "condition federal funding on the recipients’ expression of agreement with ideas with which the recipient disagrees." Alito called it a "dangerous proposition."

Srinivasan said there were limitations on the power of Congress, such as the germaneness of the policy pledge that is required. Similarly, he said the government is prevented from "leveraging its control over funding conditions in a manner that served a speech-suppressive objective."

Overall, Srinivasan said government is acting entirely properly when it decides to "partner" with organizations that agree with relevant policy objectives, on the grounds that such groups would be "more reliable and effective" in carrying out the program. Justice Antonin Scalia asked dubiously whether "partnering" is any different from just giving an organization money. "Terrible verb, anyway," Scalia said, and Srinivasan avoided it for the rest of his half hour at the lectern, using "associating" instead.

Challengers to the law seemed to be winning the case even before their lawyer David Bowker of Wilmer Cutler Pickering Hale and Dorr rose to argue. But the justices were tough on him too. Bowker said the government has some power to prefer giving funds to one group over another, but can’t require grantees to "profess a personal belief." But that led several justices to wonder whether he was conceding that government could impose policy-related conditions on funding. Bowker insisted that government may not made decisions that discriminate on the basis of viewpoint.

Bowker struggled to keep up with the rapid-fire questions from the court and seemed not to give them the clear lines they were looking for in distinguishing between acceptable government funding choices and government-compelled speech.

At one point, Bowker was caught in the crossfire between Scalia and Justice Stephen Breyer who disagreed about a point he was making concerning viewpoint discrimination.

"I don’t think you can have it both ways," said Breyer.

"Him or me? You have to choose," said Scalia, only half-joking.

Bowker cast about for a lifeline. "Mr. Chief Justice, I need your help on …" he started.

Roberts interjected, "You can always choose me, too."

Tony Mauro can be contacted at tmauro@alm.com.