Gordon on dad duty with Keira, Chase, and Winona.
By 1973 Shep was building his management company and working bicoastally (he and Greenberg would part ways the following year). In New York, Alice's road manager, Fat Frankie, set up Shep on a blind date with a chic black Wilhelmina model named Winona Williams. Both were 27 at the time, and drama was in their DNA: Leaving a club on one of their first dates, their taxi crashed into a Daily News truck; in a curiously bonding quirk of fate, the each received gashes over their eyes that required about 16 stitches apiece. Armed with pain pills, they left the hospital at 3:30 a.m. to recuperate at Shep's place downtown. A few days later, Winona said, "I have a daughter. Can I bring her over?"

She was a beautiful girl, 8 years old, named Mia; Winona's mom, Ruth, had been babysitting her at her home in Newark, New Jersey. For Shep, getting comfortable with a child was process, but he was won over by Mia's innocence. "That was my first taste of really pure love," he says, in his deceptively gruff basso. "I loved hanging out with her." Eventually, the three set up house, kicking back at Shep's mansion in Copiague, New York, on weekends, before moving in 1975 to L.A.; Shep paid the tuition for Mia's boarding school in Ojai. But with the demands of his work—to say nothing of his unease with long-term relationships—Shep and Winona broke up a few years later. He and Mia stayed in touch, Shep sending her money from time to time. When he realized she was using it for drugs, he stopped answering her letters and phone calls.

In 1991 Shep received a call from Winona: Mia had died. She was pulling into her driveway one morning when a bus hit her car, which was both tragic and ironic, given that she had recently weaned herself off drugs. "It was almost as if Satan said, 'Uh-uh—I've had you in my grasp much too long, I'm not letting you go,'" Winona says now. "And God said, 'Look, I can't interfere, but what I can do is not let it go down the way you think it's gonna go down.' And consequently, she left a legacy of having died in a car accident and not from a drug overdose."

Looking like toughs from a mob movie, Fat Frankie and Shep (silk suit, shades, dark topcoat, ponytail) showed up at the funeral in Newark, where Winona was living with her mother, working in their in-home hair salon. Winona was lovely as ever, but surrounded now by four little kids: Monique, 9; Chase, 6; Amber, 3; and a baby girl named Keira, tucked in Winona's arms. Four indescribable little faces—Mia's kids, it turned out.

Shep asked Winona what was going to happen to them. "There's a foster family that's already taking care of Keira," she said. "I don't know what we're gonna do." And some small thing inside Shep clicked.

"It seemed like something had to be done, and I had the resources," he says. "I had to make a choice: 'Do I get this out of my brain and go back to my life?' If I did, I would have to think of those four sets of eyes every time I bought a bottle of Dom Perignon."

So Shep pulled Winona aside—even after being apart for a decade, their bond was strong—and said, "I have no idea if I can give anything emotionally, but economically, I know at least for the next while, I can support all of you. So if you'll give up your life for the next 18 years and raise them, I'll pay for it."

With little hesitation, Williams signed on. The foster family caring for Keira had already pierced her ears; deeply disappointed to have to give her up, they removed the diamond studs and handed the baby over.

In the chill wind of a late October day, leaves skitter and eddy in the driveway of Winona Williams's five-bedroom Tudor home in upstate New York—the one Shep bought for her and the kids after Mia's funeral. The house is both spacious and cozy with a fire crackling in the fireplace and Williams's vibrant oil paintings—still lifes, florals, portraits of herself, her mother—lining some of the walls. Coco, a black dog with a white big, is running around out back.

At 66, Winona—fine-boned with dark eyes, wearing tight black pants, a black sweater, over-the-knee boots, and an animal-print scarf wrapped around her head—looks 20 years younger. The oldest of the kids, Monique, who works at an auto parts store nearby, is warming herself by the fire; she has the mellow, sloe-eyed beauty of Lisa Bonet from The Cosby Show. Shep bear-hugs both when they answer the door. They have an easy rapport—Shep and Winona tossing glances and weary smiles back and forth in the manner of a long-married couple.


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