Joseph Frederick, a student rebel halfway through his senior year of high school, tried the patience of his principal when he displayed a drug-referenced sign reading "Bong Hits 4 Jesus" at a public parade in Juneau, Alaska, in 2002.
The 18-year-old had fashioned a 14-foot paper banner, which he held as the Olympic torch passed across the street from his high school on a national relay leading up to the 2002 winter games in Salt Lake City.
Frederick said he wanted to capture the attention of TV cameras -- and the ire of his principal.
Principal Deborah Morse, who had previously disciplined Frederick for other acts of protest, confiscated the banner and suspended Frederick, sparking a feud that has gone all the way to the Supreme Court.
Monday, the Court will hear arguments on Morse v. Frederick, in what legal experts say could be the most significant case on student free speech since the days of Vietnam War protests.
At stake is the 1969 landmark ruling Tinker v. Des Moines, which said that students do not "shed their constitutional rights to freedom of speech or expression at the schoolhouse gate."
Since then, the Court has narrowed that ruling, giving schools the right to censor speech to maintain order and protect students from harmful messages.
But since the 1999 student shootings at Columbine High School, the legal climate has changed, and that, experts said, could influence the Court's tolerance for student free speech.
"The student has a better case than the school," said Martha Minow, professor at Harvard Law School. "But the trend of the Supreme Court has been toward curbing student speech and increasing deference to school administrators. If the school district wins here, it could have important ramifications."
The school charges that Frederick's banner promoted drug use and had an offensive religious message. Frederick said the language, which he had seen on a snowboard, is meaningless.
Frederick's case has been taken up by the American Civil Liberties Union, which agrees the message on his banner was controversial, but he had the right to express it. The ACLU further argues that student free speech restrictions since the Tinker case do not apply: The event was not school-sponsored and Frederick was not disruptive.
The controversy has drawn an array of high-profile players, including Kenneth Starr, independent counsel during the President Clinton-Monica Lewinsky investigation, who has offered his pro bono services to Morse. Morse has also received the support of school boards around the country and the Bush administration.
Also in the spotlight is Mary Beth Tinker, now 54 and one of the defendants in the historic Vietnam-era case; she was suspended for wearing a black armband to her Iowa school to protest the war. Now a nurse and advocate for student rights, Tinker said she'll be an "active observer" on the side of young Joseph Frederick.
"I had no idea at all the significance of what we did," Tinker, who was only a 13-year-old junior high student at the time of her suspension, told ABCNews.com. "But it didn't feel fair, and after talking to Joe [Frederick], he felt the same way."
Frederick was suspended for 15 days for his actions. The parade itself was not on school grounds, but Morse's lawyers argue the event was like a school-sanctioned field trip -- students were dismissed from classes, and the band and cheerleaders entertained.