Ron and Bruce Winston grew up rich and secure in Westchester and on Fifth Avenue. Even as children, the boys had markedly different personalities. Ron, the first-born favorite son, was gregarious and ambitious. He showed an early aptitude for business and often accompanied his father to the salon. Bruce was a moody dreamer, less outgoing, less athletic, less motivated, and, many claimed, less bright than his overachieving brother. The boys' aunt Lillian Winston expressed it most tartly when she told the Wall Street Journal a few years ago that Harry Winston never had much regard for Bruce's brains. " 'I have two sons,' " Harry reportedly complained to her; " 'one is a genius and one is a moron.' " One of Bruce's friends says Edna was even more disappointed in her younger son than Harry was. Soon after he dropped out of college in Massachusetts, Bruce disappeared for eight weeks, resurfacing in Florida only after the family called in the FBI.
Growing up, the brothers maintained a fragile peace; as adults they appear to have more in common than many siblings. Both are middle-aged, married, and eccentric. Both inhabit country homes and city apartments. Both love dogs, travel, and diamonds. And each despise the other.
Ron, 58, graduated from Harvard with a chemistry degree in 1963, and after a stint at NYU, where he studied rocket propulsion, he went into the family business. A committed bachelor, he finally settled down ten years ago with a striking blonde named Heidi Jensen, a 34-year-old film student who recently fled the East Coast to pursue a career as a producer. "She lives in L.A. now," Ron says sorrowfully. "She just got tired of all the fighting here." He spends his time shuttling between his Manhattan townhouse and houses in Santa Barbara and Westchester. A self-described workaholic, he is a cultivated businessman who writes poetry and dabbles in the sciences. He fancies himself a Renaissance man. He is also obsessed with Japan: He studied Zen philosophy, speaks Japanese, and devotedly tends to a small Japanese garden at one of his homes. Despite such exotic sidelines, Ron says he believes strongly in "the Protestant work ethic," and charges that his brother behaves like an immature member of the sixteenth-century feudal aristocracy.
Bruce, 54, briefly attended American International College in Springfield, Massachusetts, but dropped out to pursue a life of relative leisure. He was involved for years with est and has undergone intensive psychoanalysis. These days, he divides his time between a Fifth Avenue apartment and a sprawling country house in Katonah that he shares with his second wife, Barbara, a homemaker who keeps a low profile. Barbara has three children from a prior marriage, two of whom Bruce has adopted. Bored with business and notoriously laid-back, Bruce spends his days puttering around Katonah, driving his collection of sports cars, and sailing on the Atlantic.
"Bruce is a very sweet guy, one of those people who may be too trusting," says an acquaintance of both brothers who is prominent in the New York jewelry industry. "Ron is the exact opposite, very secretive. You never really know what he is up to. He sets his own objectives very carefully with very long-range thinking. Bruce is a spontaneous guy."
By all accounts, relations between the Winston brothers were sometimes strained but always civil while their father was still alive. After all, Harry Winston was not a man who easily tolerated dissent. Though he never had any formal schooling, he was a shrewd and commanding figure, the child of dirt-poor Ukrainian immigrants. He loved diamonds so much that his own father warned him the jewels might someday take him over. By 1932, he had opened Harry Winston, Inc., and with a blend of moxie and marketing turned it into a resounding success. During the Depression, Harry Winston singlehandedly kept the New York diamond industry afloat. At one point in the fifties, his diamond-buying power rivaled that of diamond behemoth De Beers.