At issue is whether a private school in Tennessee has a free-speech right to contact prospective students about its sports programs, even though the school belongs to an athletic association with anti-recruiting rules that bar such contacts.
Justice Antonin Scalia expressed doubt about Brentwood Academy's free-speech rights in relation to the letter, which invited 12 eighth graders at other schools to attend spring training at Brentwood.
"It was a letter from coach," said Scalia. "I mean, that to a young kid, that is recruiting."
Justices Stephen Breyer and David Souter also had pointed questions for James Blumstein, the attorney representing Brentwood, a wealthy prep school south of Nashville.
Blumstein argued the letter was harmless and was sent only to students at other schools who had already signed an "enrollment contract" and planned to attend the academy in the fall.
Souter quizzed Blumstein about the small percentage of students who sign the enrollment contracts, but then go to other schools. Why isn't there a legitimate interest in preventing recruiting among those youngsters, Souter asked.
The Tennessee Secondary School Athletic Association, which governs high school sports in the state, found the 1997 letter from Coach Carlton Flatt to be a violation of its recruiting rule. Brentwood was hit with a $3,000 fine and four years' probation by the association.
"Enforcement of the rule here imposed only a minimal burden on speech," Maureen Mahoney, an attorney for the association, told the justices. Athletic recruiting, she said, is harmful to young adults and puts too much of an emphasis on sports.
Brentwood voluntarily joined the association and was bound by its rules, she said.
Chief Justice John Roberts appeared skeptical and questioned whether letters informing students of dates for spring practice could be seen as permissible speech.
The case, which has been winding through the courts for nearly a decade now, has previously been before the Supreme Court. In 2001, the court ruled 5-4 in favor of Brentwood, saying the athletic association acted in a quasi-governmental capacity and could be sued.
A federal appeals court later ruled in favor of the school, saying the letter amounts to protected speech under the First Amendment. If that ruling stands, it would prevent all high school associations from enforcing recruiting rules.
A ruling is expected by the end of June.