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In 2000 they sought a trainer capable of developing young horses. They put their racing manager, Dottie Ingordo, on the case. Ingordo was the widow of Jerry Ingordo, a California jockeys' agent (one of his clients was the gifted and often troubled Pat Valenzuela) who had died in 1998. Their son, David, had noticed a trainer named John Shirreffs, who worked tirelessly for Marshall Naify's 505 Farms, and when Naify died in 2000, David recommended Shirreffs to his mother. Dottie not only hired Shirreffs (with the Mosses' consent), but in 2003 she also married him. David Ingordo, a bloodstock agent who buys and breeds horses for various owners, tells friends that introducing his mother to Shirreffs was "his best breeding ever."
Shirreffs, 65, was raised on Long Island and in New Hampshire, the son of an airline pilot. He says he was thrown out of two colleges for "mischief," enlisted in the Marines and in 1968 went to Vietnam. "Here I am just taking up space, and I see what other people are doing for their country," recalls Shirreffs. "I decided it was time to do something about that."
Upon returning home after a 13-month tour with Marine Aircraft Group 12 in Chu Lai, Shirreffs plotted a surfing trip to Hawaii, but he made it only to California. Like Moss he has fond memories of a muddy field. "I was riding a horse and got stuck in a mud bog in the middle of this meadow," says Shirreffs. "A guy was watching, and he asked if I was interested in helping break some young horses." That guy was named Henry Freitas, and he gave Shirreffs a job. It was not lucrative; for a long stretch in the late '70s, Shirreffs slept on a cot in the shedrow of a horse barn and kept his clothes in a car. He worked as an assistant to several trainers, climbing and learning, until Naify hired him as his trainer in '94.
Together Team Moss—Jerry and Ann, with John, Dottie and David—won the Kentucky Derby in 2005 with 50--1 long shot closer Giacomo (named for the son of Police front man Sting, an A&M artist and friend of the Mosses). Four months later the five of them went to Lexington, Ky., to buy some new horses at the Keeneland September Yearling Sale. In Barn 28 was a tall filly listed in the sale catalog as Hip No. 703. She was from the very first crop of foals sired by 6-year-old stallion Street Cry and out of Vertigineux, a 10-year-old broodmare. Here, too, there is a story.
In 1979, New York City lawyer Eric Kronfeld (who had negotiated music-industry deals with Jerry Moss) bought a filly at the Saratoga yearling sales and named her For The Flag. She was injured in training and retired at age 3 after just one race. Kronfeld eventually sent her to a stallion named Kris S, and the resulting foal was named Vertigineux. "Beautiful horse," says Kronfeld, "but the most awful ankles you've ever seen." In 2003, Vertigineux's fourth season as a broodmare, Kronfeld bred her to Street Cry, the winner the year before of the Dubai World Cup and the Stephen Foster Handicap, who was then in his rookie season at stud.
"If you are insanely wealthy, you can go to a top, proven stallion," says Kronfeld. "A.P. Indy, at the time, was standing for [several hundred thousand dollars] with no guarantee of a live foal. Vertigineux had experienced trouble carrying a foal to term. I could not risk half a million dollars. I loved Street Cry as a racehorse, and he was standing for $35,000." (One year later Street Cry would sire 2007 Kentucky Derby winner Street Sense and now stands for a stud fee of $150,000.)
On April Fool's Day 2004, Vertigineux dropped a dark-bay baby on the ground at Winter Quarter Farm in Lexington. This was the horse that Team Moss saw in Barn 28 at Keeneland, a gangly child with a terrible skin rash. "She was rangy, but very well-balanced," says David Ingordo. Dottie Ingordo-Shirreffs already loved Kris S, Vertigineux's papa, as a broodmare sire. And when the Mosses visited, the baby laid her head on Ann's shoulder, sealing the deal. Because of the rash and because of the likelihood that her lanky frame would prevent her from racing as a 2-year-old, Jerry and Ann got the yearling for the bargain-basement price of $60,000. (At the same sale the Mosses bought another filly for $625,000.)
The as-yet-unnamed bay was sent to Mayberry Farm in Ocala, Fla. The farm's owner is Jeanne Mayberry, 67, a racetrack lifer whose husband, trainer Brian Mayberry, died of cancer in 1998 at age 60. Two years later Jeanne packed her life's belongings and her two dogs into an Acura sedan, moved to Florida and purchased a 13-acre farm. "I had to buy a tractor," she says. "I read the manual and then marked all the handles with nail polish." With her daughters, April and Summer, she built a steady business breaking young horses and readying them for the racetrack. The Mosses, who had employed Brian as a trainer, sent her horses every year.
On the farm they called the rangy filly the Big Girl. One day in February 2006, Jeanne brought her 2-year-olds across the street to the dirt training track at Plumley Farm. She instructed the riders to take the babies down the stretch and around the turn. "The Big Girl was behind them, and then, oh, my God, she went right around them," says Mayberry. "I called David and told him, 'You've either got one really good horse or a lot of bad ones. And you need a name for the good one.'"
The Mosses had used names inspired by the Police before; not just Giacomo, but also Set Them Free and Styler (the surname of Sting's wife, Trudie). This time they seized on the title of the band's third album: Zenyattà Mondatta, whose meaning has never been fully explained. Why Zenyatta? "Street Cry, rock and roll, Zenyatta," says the Music Man, as if it were perfectly logical. "There's also a Mondatta. She never got to the races."