In 1996, Wolffer’s company, Euro Investors, acquired 1,800 acres of the valley by assuming a $12 million mortgage from the previous owner, who was teetering on the brink of foreclosure. But some of his neighbors took a dim view of Wolffer’s plans for the property. "The nightmare that almost happened" is how an organization called the Stewards of Waimea Valley described a 2000 real estate listing in which Wolffer, after a series of battles with local environmentalists and preservation committees, tried to sell the entire valley for $19 million. To Hawaiians, this listing was like putting the Sistine Chapel up for sale, the Stewards claimed.

The no-money-down Waimea Valley acquisition was just the kind of risky, but promising, deal that whets the appetite of this developer, based in Long Island, N.Y. The property comprises a pristine ecosystem of mountains, streams and forests, harboring endangered species on grounds the locals consider sacred. Wolffer originally envisioned an ecotourism development there, but, as he sees it, he was never able to obtain permission to do anything at all.

"It’s impossible to do business in Hawaii," Wolffer claims, with more philosophical resignation than venom. Ruddy faced with sky-blue eyes and a propensity for appearing in Hamptons party photos next to much younger women, the 67-year-old Wolffer has developed a win-some, lose-some outlook on his investments. What he calls "my 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.

"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."

Located on the island’s South Fork, the 170-acre Wolffer Estates is the scene of myriad parties for select circles of friends and tasting fetes for the community. The complex encompasses a 100-acre horse farm with an Olympic-size dressage ring, a 55-acre vineyard and a winery that produces about 13,500 cases a year, mainly Chardonnays and Merlots. While the wine world has developed a respect for Long Island Merlots in the past few years, Wolffer’s Premier Cru Merlots set the standard, according to New York Times wine reviewer Howard Goldberg. Generally an enthusiast for New York state wines, Goldberg once went so far as to declare Wolffer’s 1997 Merlot so voluptuous as to be "bottled pornography."

The Premiere Cru vintages of the 21st century–the 2002 was released last October–retail for $125 a bottle, the first Long Island wines to sell for more than $100. Wolffer’s winemaker, Roman Roth, is well known among Hamptons wine aficionados.