Those who turn left eventually arrive at a 127-acre hilltop campus that was once a Civil War-era plantation. Ensworth features the latest in educational fads and furnishings. Its freshmen study a mix of physics, biology, and chemistry, instead of focusing on just one of the three, as at most schools. For the dramatically inclined, a 665-seat performing-arts theater is under construction. Each of Ensworth’s 400 students is provided with not only a laptop computer but also a personalized fitness program; they pump up in a 10,000-square-foot weight room larger than that of Nashville’s N.F.L. team, the Tennessee Titans. “It’s like a school on steroids,” says the father of a prospective student.

In Founders Hall, a display lists the school’s principal backers. The first eight names: Tommy and Trish Frist, their three children, and their children’s spouses. Tommy and his wife funded the lead gift, about $35 million, from their personal fortune. Their daughter, Trisha Elcan, and her husband, Charles, donated the land, which they had purchased for $4 million.

The family made sure that its investment was well spent. Tommy and Trisha kept close tabs on construction, visiting the site regularly, says project architect John Prokos. “He wanted Ensworth to have its own unique identity”—different from Montgomery Bell’s. Tommy and Trisha toured other new prep schools, alongside Ensworth administrators seeking guidance. The night before Ensworth High opened, Trisha took a broom and swept up rubble in the halls.

Montgomery Bell’s students and faculty watched the newcomer warily. Kevin Seitz, who graduated from M.B.A. in 2006 and attends Harvard, says he and his teammates on the cross-country team used to detour from their normal practice route to run past the Ensworth campus and marvel at it. “They have so much land over there,” he says. “That’s one thing we were jealous of.”

Ed Caudill, a former Montgomery Bell math teacher who joined Ensworth’s staff and has sent his three children to the school, says the relationship between the two institutions is “more competitive than I think it should be. It’s brother against brother.”

The Frist dynasty’s contribution to Nashville is hard to overlook, because it’s branded on three of the city’s premier tourist attractions. The ­Country Music Hall of Fame boasts a Frist Library and Archive, while the Cheekwood Botanical Garden and Museum of Art features a Frist Learning Center. The crown jewel is the Frist Center for Visual Arts in downtown Nashville, where even the parking-lot traffic cones are labeled frist.

Few in Nashville begrudge this self-promotion. Here, the Frists are widely heralded as health-care visionaries who helped diversify the city’s economy beyond banking and insurance. H.C.A., where Tommy served as chief executive from 1987 to 1994 and again from 1997 to 2001, remains Nashville’s largest corporate employer and has spun off some 25 publicly traded health-care companies in the region. Tommy successfully lobbied pharmacy-benefits management firm Caremark to relocate to the city in 2003. Other businesses that have subsequently shifted operations to Nashville include Nissan Motor and building-products supplier Louisiana-Pacific.

An Air Force flight surgeon during the Vietnam War, Tommy co-founded H.C.A. in 1968 with his father and Jack Massey. In 2006, when Tommy, Bain Capital, Kohlberg Kravis, and Merrill Lynch took H.C.A. private in a $33 billion leveraged buyout, he sold back 16 million shares valued at $892 million.

Tommy still chairs H.C.A.’s former foundation, which was renamed the Frist Foundation in 1997 and supports an array of Nashville nonprofits. For the most part, the foundation isn’t giving away Tommy’s own fortune; it derives most of its $210 million in assets from company stock options that it cashed out. In recent years, it has scaled back funding for some causes to subsidize the Frist Center for the Visual Arts.