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In 1997, Brentwood Academy's coach Carlton Flatt wrote a letter. Its content and purpose seemed innocuous enough. Sent to eighth grade students who had enrolled in Brentwood Academy for the upcoming Fall term, the letter invited incoming freshmen to join Flatt in two weeks of spring football practices. Printed on school stationary and openly referring to the sport's governing association, the TSSAA—"having officially enrolled at Brentwood Academy, the TSSAA allows you to participate in spring football practice"—the letter hardly seems an instrument of subterfuge or willful disobedience.

Nonetheless, ten years, millions of dollars and hundreds of billable hours later, the legal case that ensued still simmers in the U.S. court system. Last June there was a big explosion—Brentwood Academy lost its First Amendment argument in the U.S. Supreme Court. Coach Flatt, it turns out, should not have written that letter. Or, rather, he could have written all the letters he wanted had Brentwood Academy not agreed to become a member of the Tennessee Secondary School Athletic Association. The TSSAA, which regulates interscholastic sports among its 380-member schools in the state, prohibits "hard-sell" tactics in the recruiting of students.

What happened between the private, non-denominational Christian Brentwood Academy and TSSAA (nominally a volunteer association governed by public school principals, but widely considered the only game in the state), is permanently enshrined in America's legal history as a record-breaking court battle. It's the Roe v. Wade of high school football, and some legal scholars suspect that its ultimate result may reach far beyond school athletics and diminish the power of free speech defense nationwide. Brentwood Academy v. TSSAA went to the federal judge in Nashville twice and wound up in the U.S. Sixth Circuit Court of Appeals three times. Even the U.S. Supreme Court, for the first time in the nation's history, found it necessary to weigh in on matters of high school football (and not once, but twice). Both the Clinton and Bush administrations had commented on the case, at different times supporting different sides. Brentwood Academy v. TSSAA is studied at law schools and is as viable conversational currency at a Washington, D.C., soiree as it is at a Grundy County barbecue cookout. And why wouldn't it be? It's a case of rich versus poor, of underdog versus oppressor, and one where both parties see themselves as the oppressed. Ten years into a legal morass created by Flatt's missive, and in the aftermath of the latest weighing in by the U.S. Supreme Court, neither party is backing down.

In a state where high school football means no less to its people than the Olympics did to the Ancient Greeks, it's fitting that the battle itself has turned epic in proportion. And like any good drama, the roots of Brentwood Academy v. TSSAA extend back decades before Coach Flatt's litigation-triggering letter, back to the very inception of Brentwood Academy in 1969. Just as would any private school, Brentwood Academy sought to rise above public schools in academics and athletics. But succeeding in sports required talented athletes—students that public schools do not want to give up.

In November 1991, Brentwood Academy went to Loretto, Tenn., to play a small high school that was undefeated that season (10-0). Brentwood Academy's strategy was to find the shortest guy on the opposing team—a cornerback in this case—and throw the ball over his head, over and over again. The cornerback, who happened to be the son of Loretto High School's principal, David Daniels, was worn out, and Brentwood won the game. "I hated it for him," says Flatt, who now teaches math at Eagleville High School in Murfreesboro. The private school continued to ride its strategy of playing—and beating—smaller schools, slowly graduating to larger ones. In 1995, during the Clinic Bowl at Vanderbilt Stadium, Brentwood Academy beat Rutherford County's Riverdale High School.

By 1997, Brentwood Academy had established itself as the most powerful preparatory football program in state history. It had nine state championships under its belt. Flatt, who would win his 10th state championship in 2006 before retiring from coaching and is the state's winningest football coach with 343 career victories, was largely credited with Brentwood's success.

With success came plenty of rumblings regarding questionable recruiting tactics—not unusual for a program so good for so long. In the 1995 Clinic Bowl game, Riverdale's principal and football coach Hulon Watson was overheard by a Chattanooga Times Free Press reporter at halftime pledging to make sure Brentwood Academy did not get another chance at a championship trophy. According to depositions obtained later by Brentwood Academy lawyers, in early 1996 Watson called a secret meeting of 26 Middle Tennessee high schools, proposing a split between public and financial aid, or private, schools. "I thought the playing field was not level for the public and private [schools]," Watson said in depositions, citing evidence that private schools, which constituted roughly 16% of all Tennessee high schools, were winning 55% of championships. Given that most of the the principals with whom Watson consulted prior to the TSSAA legislative council meeting—as well as most of the council members themselves—led schools that had fallen victim to Flatt's team on the playing field, the outcome was hardly surprising: the council approved the split into Divisions I and II. But that move didn't erect the wall between public and private schools, as Watson advocated.

In 1997, rumors surfaced of illegal channeling of public school athletes to Brentwood Academy. TSSAA executive director Ronnie Carter launched an investigation, but the channeling charges were soon dropped. Instead, Carter seized upon the spring practice letter written by Coach Flatt, which was discovered during the investigation. TSSAA fined Brentwood Academy $3,000, citing its policy prohibiting "undue influence on a student (or) his or her parents ... to secure or to retain a student for athletic purposes," which also bars coaches from contacting students prior to official enrollment at the school. (Though the students had enrolled in Brentwood Academy in one sense, the TSSAA defined "enrollment" as first day of school plus three days.) With the fine came a four-year probation and two-year banishment from state playoffs. Incensed, Brentwood Academy appealed the decision to TSSAA's board of controls, bringing with them several lawyers for good measure. The board upheld the punishment. Brentwood Academy sued.

In one corner there was Jim Blumstein, Vanderbilt University Law School's celebrated constitutional scholar. He was the big-picture strategist who crafted the First Amendment doctrine for Brentwood Academy. The school also retained well-known litigator H. Lee Barfield, of prominent Nashville law firm Bass, Berry & Sims, a legal powerhouse in its own right. Representing TSSAA was the inconspicuous Franklin law firm of Wilbert & White (presently Colbert & Wilbert). "I've never seen anything else like this [case]," says Rick Colbert, who inherited TSSAA as a client from his mentor Charles Hampton White, who retired from law practice as the case slugged through the court system.

While Brentwood Academy had its pride at stake, so did the TSSAA, unbeaten in court since its inception in 1925. TSSAA's management, including Carter, saw their recruiting regulations as the only thing preventing private schools from applying college-style recruiting gimmicks to prepubescent teens.

Perhaps more tellingly, soon enough the organization had no choice but to continue appealing the case, especially following the early injunction against TSSAA by Judge Todd Campbell. An early defeat would have meant paying millions of dollars in attorneys' fees, an especially daunting prospect following the 2001 Supreme Court decision against the TSSAA, a 5-4 split decision that sent the case back to the Court of Appeals.

By the end of 2007, Colbert estimates that both parties had spent upwards of $7 million on the case. "Brentwood Academy hired a stable of good and well-financed lawyers that kept their doctrine alive in court, and tried to get us to cave in. That is my simple view of the case," Colbert says. Colbert criticizes Brentwood's First Amendment doctrine as a weak strategy. "There is a lot of gray in the law," he says. "The First Amendment runs along different lines, and you can't just reach into different cases and grab some sentence and apply it out of context."

Gillian Metzger, a constitutional law scholar at Columbia Law School in New York City, is not surprised that the Supreme Court did not buy Brentwood Academy's First Amendment argument, especially since, in this case, it analogized the matter to employment within the government, and the Supreme Court is known to support restriction of speech of government employees. "The [2001 decision] was more of a surprise," Metzger says. "This one, whether it makes doctrinal sense or not, it makes common sense." Not surprisingly, Blumstein regards the latest Supreme Court decision far less sanguinely. "Anytime you voluntarily subject yourself to the government's regulation, the court seems to apply a lower level of First Amendment protection, and it's very troubling," Blumstein says. "The decision was not reasoned, it was pronounced. The justices didn't cite the relevant precedents; the court didn't discuss the cases we presented."

Barfield calls the outcome of the latest ruling "anti-American," stressing that the big losers in this case are the underprivileged public high-school students: "If a child is an athlete, the private school may not contact the parents.* Public and private schools have different recruiting rules, and the public schools control the enforcement mechanism within the TSSAA."

While the case is not over—Brentwood Academy is awaiting a Nashville Federal Court hearing on the remaining anti-trust and equal-protection claims—Colbert is glad that TSSAA chose to defend itself all these years, in many cases against long odds. "You could draw football analogies and say we won it on a fourth-quarter touchdown, but I have a hard time comparing it to a sport. It's hard for me to envision Mr. Blumstein or H. Lee Barfield in helmets and shoulder pads." Such levity-laced comparisons are to be expected from the side that has most recently reached the end zone, especially since this particular contest might well have reached the end of regulation. But given the swings of momentum on both sides of the ball, it might be unwise to rule out overtime just yet.