Though other women at the fund-raiser wore gowns, Mrs. Ross was festive-business in a glossy brown pantsuit, the smile warm and dimpled, and she had mastered the Clinton shake and shoulder grip. At 58 (she's now 59), she was still a beauty, her face lacking the paint job that often comes with a decade’s redecorations.
They were all there to celebrate and support Ross’s glorious, whimsical homeschooling experiment that had evolved muscular legs. In 1991, the Ross School began as a tutorial service for Mrs. Ross’s daughter and her little friends. They wouldn’t just study the Great Wall of China—they would travel there. Its classroom consisted mainly of the passenger cabin of a Gulfstream, which was replaced within ten years by a compound of East Hampton buildings. Her project had become a swanky, architecturally significant ashram of higher learning out there in the woods.
But like any institution backed by a Carnegie or a Vanderbilt or a Rockefeller, the entire operation needed to be sustainable, like the organic food in the cafeteria that started a revolution in school dining nationwide and the Brazilian ipe paneling. A staggering philanthropy had been committed: To launch and support her school, Mrs. Ross had spent $330 million and counting, according to a board member. It was why she was presiding over this roundup of South Fork breeding pairs on a Saturday night in December, in a school gym surrendered to a klieg-light-trimmed chuppa and a creative caterer’s hoodoo.
And now: It was time to extend a very big welcome to “our visionary,” as Tim Kelley, the brand-new head of school, pleasingly described her. (There was usually a newish person in charge padding around, the ten-plus others having been discreetly dispatched by shining thunderbolt, gone for “personal reasons,” as it was sometimes gingerly phrased.)
“Look, what Courtney Ross has done here is pretty amazing,” says architect and Ross parent Daniel Rowen. “A lot of my clients are strong-willed people—Martha Stewart, Larry Gagosian, Ian Schrager. They’re not warm and cuddly, but maybe that’s not why they were put on this planet.”
And who among the local bien-pensants could question her commitment to educating the blacks and Latinos and Shinnecock Indians of the region? Every year, $1 million (or more) of her personal fortune is docked to pay financial aid for almost half her students. Of the first five graduating classes, 33 percent were the first in their families to enroll in college.
Husband Steve’s tan photo was a postage stamp in the Starlight Ball program. “Not much is known of Steve Ross’s interest in education,” Mrs. Ross rightly observed in her plucky newscaster voice. He was a financial savant who didn’t read books, say friends, recalling the phony gilded spines in the Potemkin bookcases lining the 10,000-square-foot Park Avenue double duplex he shared with Courtney, his third wife.
That December night, the Ross School was honoring one of the mothers of the Republic, Christie Brinkley, and the ex-model wept like Miss America when Mrs. Ross handed over some roses. Later, Brinkley’s daughter Alexa Ray Joel would sing. Among the community’s scarce winter homesteaders, the Brinkley-Cook-Joel clan is handled with care, like a nest of endangered piping plovers. “Attention press,” reads a handout. “Please do not approach or speak to Ms. Brinkley’s children. You are permitted to film or photograph Alexa Ray Joel’s first song only.”
Always exquisitely attuned to her image, tonight Mrs. Ross made sure she was photographed with a Somalian refugee she’d recruited from Ross’s sister school in Sweden.
Those who know her well see Ross’s admirable commitment to diversity as rooted in her own past. “Courtney has a real southern sensitivity to overcoming the stain of southern segregation,” says her longtime friend the Reverend Jesse Jackson.
Mrs. Ross’s hometown, Bryan, Texas, is still a small town, dominated by Texas A&M University nearby. Her grandfather George Stephan owned the local icehouse and Coca-Cola bottling franchise. And when George Stephan died, his daughter, Courtney’s stylish, attractive mother, Gloria, took over as president.
Courtney’s father, Elbert Sale, was winkingly called “Chic Sale,” old-timey slang for an outhouse—somebody might say, “I’m going to the chic sale”—and almost certainly a nickname bestowed when he was an A&M cadet. It was Chic, a good ol’ boy whose hands by the end of his days shook so bad he could hardly light his smokes, who put junk-food-vending machines in A&M’s dorms.
For Gloria to be a CEO, running the business and giving orders, was an anomaly in Bryan. “She didn’t mind telling it like it was, and she’d cuss a little bit,” says judge Tom McDonald, who grew up with Courtney and her two sisters. The Sales were one of the richest families in town, charter members of the Briarcrest Country Club. The girls were sent to Holton-Arms, a boarding school just outside Washington, D.C. Of the three downtown movie theaters in Bryan, the only one that admitted blacks had a “colored” balcony. Those cotton plantations out along the Brazos River drew migrant workers from Mexico, some of them almost pure Indian, who came down from the Sierra Madre. West of town was a great big messy labor camp.
“She came out of an apartheid culture,” Jackson says of Mrs. Ross, “and she chose to overcome it.”