Organizations that ignore Tommy’s views about how his money should be spent do so at their financial peril. Several years before he walked away from Montgomery Bell, he had discussed a multimillion-dollar gift with another Nashville institution, Vanderbilt University, where he had earned a bachelor’s degree in 1961 and where he served as a trustee. As was the case with Montgomery Bell, the offer came with strings attached. Tommy, who planned to donate H.C.A. stock, wanted the right to decide when the university would sell the shares. Vanderbilt prohibits such a restriction, and Tommy never made the gift. The chancellor at the time, Joe Wyatt, says the university would not have waived the rule because, since Tommy was a trustee, a waiver would have appeared to favor an insider.

The final break came when Vanderbilt chairman Bronson Ingram died in 1995. As vice president of the board and its richest member, Tommy was viewed by many as Ingram’s likely successor. But several trustees opposed his appointment, saying it would create a conflict of interest: Tommy’s company, H.C.A., owns nine hospitals in the Nashville area that compete with Vanderbilt University Medical Center for patients, and Tommy had once broached the possibility of H.C.A. buying Vanderbilt’s hospital. After Vanderbilt signaled that Tommy wouldn’t be named to the chairmanship, he announced that he wasn’t a candidate. “My sense was, when Tommy didn’t get the spot, he went away mad,” says a former Vanderbilt administrator. In September 1997, Tommy resigned from Vanderbilt’s board.

A month later, he and other family members gave $25 million to one of Vanderbilt’s top competitors for Southern students: Princeton University. Tommy’s two sons and his brother Bill had gone to Princeton, but Tommy had never studied there. Soon, Princeton renovated a physics building into the Frist Campus Center. A person familiar with the university’s fundraising says that Tommy still contributes modestly to Vanderbilt athletics and its nursing school (which has a wing named after Tommy’s wife), but the university is “definitely off his list” for major donations. Around campus, according to another insider, Princeton’s windfall is remembered as the “Fuck you, Vanderbilt” gift.

One alma mater down, one to go. Tommy’s overture to Montgomery Bell came in late 2001 when he approached the executive committee of its board with his stunning nine-figure offer. At the time, no one had ever given such a large gift to a U.S. prep school. The biggest single donation ever to Montgomery Bell had been about $10 million, and the school’s assets then totaled $69 million.

But Montgomery Bell would receive the prize only by merging with its longtime feeder school, Ensworth, to create a coeducational K–12 school. Founded in 1958, at a time when court-ordered desegregation of public schools prompted many white families to seek private education, Ensworth’s lower school teaches boys and girls through eighth grade on a Tudor-style campus (which includes—what else?—Frist Hall) only a quarter-mile from Montgomery Bell. If Montgomery Bell refused, Tommy indicated, he would build a high school for Ensworth.

In a statement provided by an H.C.A. spokesperson, Tommy says, “The establishment of a coeducational secondary school was of particular interest to me, as I have long believed in the importance of parity in education for our young men and women.” According to a friend, Tommy regards single-gender schools as relics of an era when Southern girls weren’t supposed to go to college or have careers. Tommy’s daughter, Trisha, has said that when she graduated from eighth grade in 1979, she felt her only option was Nashville’s elite private high school for girls, Harpeth Hall (best known as actress Reese Witherspoon’s alma mater). Around that time, Tommy encouraged Harpeth and Montgomery Bell to merge. Both schools balked.

Nashville does boast another premier private coed K–12 institution, University School. But it may clash with the Frists’ style. University School caters to the city’s intellectual, rather than social, elite. Its high school doesn’t have a football team. Parents, many of whom belong to Vanderbilt’s faculty or staff, lean politically liberal and Democratic. One is likely to see a Prius with an Obama sticker in the carpool line at University School, versus a Suburban with a McCain decal at Montgomery Bell or Ensworth; McCain held a campaign rally at M.B.A. last February. Montgomery Bell has an indoor rifle range; University School has a Gay-Straight Alliance.

When Trisha and her brothers began having daughters, Tommy resumed his campaign for a coeducational prep school. Trisha has three daughters at Ensworth, the eldest in eighth grade. “I’ve heard people associated with M.B.A. say, ‘If Trisha had three sons, this never would have come up,’ ” says an Ensworth insider.

Montgomery Bell’s executive committee referred Tommy’s proposal to the full board, which also included his younger sister Mary Louise’s husband. After much behind-the-scenes ferment, the board rejected the offer without even taking a vote. The consensus was that an all-boys school was both central to Montgomery Bell’s identity and an educational approach still sought by many Nashville parents.

Daniel McGugin, then assistant football coach at Montgomery Bell and now head coach, was privy to the board’s discussions because his father was an M.B.A. trustee. M.B.A. turned down the offer, he says, because educating boys “is who we are, what we do.” Tommy’s vision was “a pretty fundamental difference.”