Fashion designer Calvin Klein’s Southampton Village mansion—or, some would say, castle—started coming down this month, ending an era—or, some would say, error—that dates back to the 1980s, when financier Barry Trupin reimagined the estate without a building permit in a way that flew in the face of zoning codes.
Mr. Trupin’s illicit expansions of the mansion he renamed Dragon’s Head resulted in $1 million worth of legal costs and years of litigation for Southampton Village. He had added 20,000 square feet to the house before the village stopped him in 1984. Newsday, at the time, called the remolded house “the height of hideosity” and critics often referred to it as “Disneyland on LSD.”
Now the mansion, which Mr. Klein paid $28.9 million for in 2003, is being torn apart by backhoes and the remains are being crushed and hauled away to make room for Mr. Klein’s new oceanfront home, a sleek, white, modern structure, with 13,000 square feet of floor area above ground. It will be three buildings attached underground.
Long before the Meadow Lane home became Dragon’s Head, it was horticulturist Henry Francis du Pont’s Chestertown. He built the house in the mid-1920s and named it after the colonial town in Maryland from where he imported pieces of 18th century American homes that demonstrated the popular architecture of the era.
“Du Pont bought these colonial houses and had them stripped of their interior wood details, from cupboards to moldings, to wainscoting,” said Anne Surchin, an East End architect and writer who included Chestertown in the 2007 book she co-authored with fellow architect Gary Lawrance, “Houses of the Hamptons, 1880-1930.”
The pieces of the colonial homes in Chestertown the town were reinstalled in Chestertown the house.
“It was a grand Georgian house, and it was magnificently and intelligently designed,” Ms. Surchin said. “It really made use of the site in a way that was ingenious.”
Architect John Cross designed Chestertown, but Mr. du Pont was very hands-on during the process, down to picking the brands of grease traps in he kitchen, Ms. Surchin said. “He couldn’t keep his nose out of anything.”
Local architectural historian Zachary Studenroth surmised that Mr. du Pont later may have moved all of the historic architectural elements to his Delaware estate and museum, Winterthur, before he died in 1969, or they might have been compromised when Mr. Trupin renovated the house in the 1980s.
Even the brick skeleton of Chestertown barely remained by the time Mr. Klein moved into the estate, according to Mr. Klein’s architect, Michael Haverland of East Hampton
When Mr. du Pont died, Chestertown was sold to “Baby” Jane Holzer, a Warhol Superstar. When Ms. Holzer and her husband, Leonard, defaulted on their mortgage a few years later, the house was auctioned on the steps of Town Hall to coal industrialist John Samuels III.
Mr. Samuels sold Chestertown in 1979 to Mr. Trupin, who reconstructed it without village approval into a faux-Norman chateau, replete with ostentatious turrets. The house was built up so big and tall and that to resolve some of the height issues, the first floor was buried in dirt so the mansion would appear shorter.
The Trupins’ Meadow Lane neighbors and the community at large were shocked at Mr. Trupin’s disregard for the law and how he could do so much under the village’s nose.
“He poisoned things for people in government in Southampton Village for quite some time,” said Peter Boody, the editor of The Southampton Press from 1984 to 1998 and the editor of The East Hampton Press from 2007 until earlier this year.
When it came to light that the mayor at the time, Roy Wines Jr., had the plumbing contract for the mansion, the controversy deepened. He was ousted from office in 1985 when he was defeated at the polls by Bill Hattrick, who was the chairman of the Zoning Board of Appeals.
“It was the biggest political upheaval, I think, that had ever wracked the Village of Southampton,” Mr. Boody said.
The 1985 mayoral battle became very personal, he said, and Mr. Hattrick would speak in front of local groups, like the Southampton Rotary Club, and get nearly teary eyed talking about his white knight battle against the forces that allowed Dragon’s Head to be built.
Mr. Hattrick was successful and the “old guard that had run the village for years were sent packing,” Mr. Boody said.
“It’s an epic of sorts that the house caused so much controversy,” Mr. Hattrick said Tuesday, “and to see somebody pay $29 million for it and then tear it town—at least it will be the right height.”
The only reason he decided to run, and likely the only reason he won, was the Dragon’s Head issue, Mr. Hattrick said this week. He also expressed great respect for the man he ousted from office 24 years ago: “I don’t think anybody in this village has ever worked harder for the village than him,” he said of Mr. Wines.