Like most of the Hamptons estates created after the 1960s, Wolffer’s arose on land that had been held by generations of potato farmers, who sold it for more money than they ever dreamed possible. Wolffer still calls it "the farm," though the three-bedroom farmhouse he bought for $163,000 in 1978, with only 14 acres around it, has morphed into a Tuscan-style villa. "I bought more land as I had more money," Wolffer notes. "It was a constant cash outflow. Eventually my accountant told me, ‘Christian, I want you to stop this. You can’t afford debt.’

"On the advice of my accountant, I started looking for a cash crop. I tried a nursery, but that was blown out by Hurricane Gloria in ’85. Then, when my children and I were skiing in Europe, I met Alan Stillman, the restaurateur. One day he invited us to a dinner for his wife’s birthday. He was serving a very good wine grown on a small estate. I thought, ‘Why don’t I get into wine?’ It looked like fun. It was always my father’s dream to have something like that. He, unfortunately, passed away in 1984; we didn’t start the winery until 1987, and made our first 200 bottles in 1989."

His most rewarding business venture is the one that seemed the most uncertain of all when he stepped into it 20 years ago: creating a Long Island wine worthy of a three-figure price tag.

Wolffer had dreamed of owning land throughout his war-ravaged childhood in Hamburg. His family once had property, but lost everything in World War I; he was born into poverty. "I am," Wolffer notes, "completely self-made." That is, except for the roughly $50 that his father gave him when he was 19, which helped get him to Mexico. There he started learning how to invest. "I started with OPM: other peoples’ money," he says. "I never had a grand vision. I was thinking of enough to feed me the next day. I learned early you can only make money on a leveraged basis. It happened that there were a lot of ventures in real estate."

In contrast to the Hawaiian fiasco, many of his deals have borne fruit. One he recalls fondly began in the mid-1990s. He purchased the Rice Hotel in Houston, then a boarded-up landmark–John F. Kennedy had slept there the night before his assassination–with nothing down except a commitment to assume the mortgage and renovate it. Wolffer invested about $1 million in the restoration and spent two years negotiating with Houston’s City Council over the building’s future in a successful bid to convince the city to finance a large share of the restoration as part of a local revitalization. He eventually sold his stake for $5 million. Today the Rice is a luxury residential and retail complex. "So," he says, "from not investing a dime to investing a million and making $4 million is not bad. You need to be adventurous. If you have common sense, I think you can improve any situation."

Wolffer is also given to mulling over situations that did not turn out ideally in a life of travel and deal making. "I can approach everything from a practical point of view," he says. "What I never had the chance to do was have an intellectual approach to something. But you cannot complain, because you have this life and you make the best out of it."

Twice divorced with four children–at least one of whom is very much interested in wine–and seven grandchildren, Wolffer describes himself as "not always a great family man." These days though, he thinks of his winery staff as a second family.

The Long Island estate has become, he says, "The only thing I did other than making money." And of money itself? Even a $35 million hit like the one he took in Hawaii renders him sanguine. "In my opinion . . . there are more important things in life, but [money is] certainly helpful, especially if you live in New York."

Jan Alexander is a features editor for Worth.