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CHAPTER ONE

A COMMITTED DUDE

The quest began as simply as this: growing up in the late 1970s, Bayard Winthrop had a favorite shirt.

The shirt was a cotton flannel, heavyweight, with a plaid pattern of blue, white, and gray. Bayard wore it to hockey practice in Greenwich, Connecticut, where he grew up. He took it along when he attended boarding school in Massachusetts. All through his boyhood, until he outgrew it, he wore that plaid flannel shirt. An item of clothing becomes cherished because it conjures special meanings and emotions for the wearer. Flannel made Bayard feel cool. "It looked great," he recalled, "and I thought it said something about me—that I was physical and capable and outdoorsy."

Admittedly, his name didn't exactly telegraph "rugged flannel shirt." Bayard (pronounced BY-erd) Winthrop is a descendant of one of the oldest and most distinguished families in America. A university, a hospital, a Harvard residence hall, and towns in Massachusetts and Maine were all named after his forebears. Bayard's great-great-great-great-great-great-great-great-great-great-grandfather, John Winthrop, was an English Puritan who became the first governor of the Massachusetts Bay Colony. In 1630, before reaching the new world, he delivered the famous "City upon a Hill" sermon later quoted by several U.S. presidents, most famously Ronald Reagan in his 1980 election eve address to assert America's exceptionalism. A distant uncle, Robert Winthrop, was a noted philanthropist, sportsman, and conservationist who campaigned to save the mallard duck. Indeed, the family name carried the unmistakable ring of Yankee blue blood. Once, when he was in college, a professor calling roll quipped, "Bayard Winthrop—not a lot of history in that name."

Bayard's father, John, grew up on the north shore of Massachusetts and on Park Avenue, and like every man in his line going back generations, he attended Harvard. He went to work as a wealth manager for the family firm, Wood, Struthers & Winthrop. In the mid-1960s, he settled his young family into a big white Colonial on seven acres bordering "back country" Greenwich. Like his two older brothers, Jay and Grenville, Bayard was sent to the elite private school Greenwich Country Day. It was grooming for a comfortable life of profiting from an ever-upward climb in the stock market and enjoying cocktails and backslaps at the Round Hill Club. At some point along the success trajectory, the family name would be burnished through charitable giving and volunteer work.

But in 1976, when Bayard was seven, his parents divorced acrimoniously, and the picture of old-money comfort and privilege turned more complicated. John kept the estate and much of the couple's social circle, while Bayard's mother, Deborah, who had grown up adjacent to wealth but not of it, struggled to find her place as a newly single mother in a clubby town. Deborah and the children moved to a smaller house a few miles away that she received in the divorce settlement. She got her real estate license and eventually sold the house and pulled out the equity, moving her sons to a less affluent part of town. She would repeat that maneuver every few years throughout Bayard's childhood, selling and moving to another, often smaller house. Bayard began his life amid the rolling pastureland and fieldstone walls of the Connecticut countryside. Five moves and ten years later, home was a first-floor condo unit hard against the I-95 overpass.

Greenwich back then was more economically diverse than it is today. There was a Woolworth's on main street. Amid the old-money WASPs, there were middle-class neighborhoods where the tradespeople lived. Bayard and Gren lived with their mother (Jay had gone to live with their father) and they existed more in this workaday world. One of Deborah's longtime boyfriends drove a town car as a chauffeur. Another man in her social circle was a mechanic who rode a Harley Sportster. Gren opted to attend the public high school, where he was on the hockey team and hung out with a rowdy crowd. Deborah sometimes took in boarders to help pay the bills. The boys were semi-feral latchkey kids, mostly raising themselves while their mother worked and struggled to cope emotionally. They dubbed one of their favorite dinners—vinegar poured over saltine crackers—"super sogs."

Aside from that favorite flannel shirt, Bayard didn't show much interest in clothes. He was a heavy kid, so most clothing didn't flatter him, and he was never very materialistic. His mother told me that Bayard's eldest brother, Jay, was the sharp dresser in the family, sporting a khakis-and-polos East Coast Ivy look. "Whereas Bayard," she said, "I once looked in his closet, and I said, 'Bayard! You haven't got four pieces of clothing.'"