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What would a Donald Trump North Fork have looked like?

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Long before his political aspirations took shape and millions of Republican voters selected him as their presidential nominee, Donald Trump was a developer. Well-known for his casinos and reality television appearances, Mr. Trump has spread his brand across the globe.

In at least three instances, he has also tried to conquer the North Fork.

From proposals for a NASCAR track to housing at the former Grumman property in Calverton to a golf course and condo development on Plum Island, the flamboyant Mr. Trump has had his sights set on the North Fork for decades.

Each of his proposals, however, has been stymied by zoning rules that prevented them from getting off the ground.

Whether these plans ultimately would have helped or hurt Riverhead and Southold towns is still up for debate. But elected officials and advocates agree: A Trump North Fork would certainly look different.

Mr. Trump’s biggest target was the former Grumman facility gifted to Riverhead Town by the federal government in 1998 for economic development. That property, now known as the Enterprise Park at Calverton, or EPCAL, was originally set to be sold as a single block to a developer — and Mr. Trump was one of the contenders.

In March 1999, he announced he wanted to build a Trump Superspeedway NASCAR track there, offering to pay $55 million for the entire 2,900-acre property. As part of the proposal, Mr. Trump also planned to build a golf resort and hotel, residences and an industrial park for the site, according to a 1999 News-Review article.

Vincent Villella, who served as town supervisor when Mr. Trump made his proposals to Riverhead Town, said the developer had the backing of members of the France family, which owned NASCAR at the time. Mr. Villella recalled getting into a helicopter with Mr. Trump to fly over the property with then-CEO Bill France Jr. and his son Brian.

Mr. Trump and Brian France were enthusiastic about the idea, but the eldest France shot down the idea for the track, saying the site’s limited road access made it too big a hassle.

“Trump was a little pissed off, you could see,” Mr. Villella said in an interview this week. “The son was, too.”

Without the backing of NASCAR, Mr. Trump failed to meet the deadline for an offer on the Grumman property at the end of March 1999. But just a few weeks later, he was back with a new proposal for the site: a self-contained community with 1,500 houses and world-class golf courses.

According to Mr. Villella, Mr. Trump raised his offer for the entire property to between $90 million and $95 million.

But the idea stalled immediately. At the time, the town had just passed a new set of zoning plans for the site that didn’t allow that much housing. According to an April 1999 News-Review story, the town’s Riverhead Development Corporation committee rejected the idea soon after Mr. Trump made his pitch.

But Mr. Trump was “stubborn” and refused to reduce the amount of housing, Mr. Villella said.

“He said, ‘What the hell is wrong with this town?’ ” Mr. Villella recalled. “Everything just fell apart when he couldn’t get the housing.”

Requests for comment from Mr. Trump — who at the moment is quite busy with his presidential campaign — weren’t answered this week.

Phil Cardinale, a former town supervisor who was a councilman in the late 1990s, said it’s important to remember the context of Mr. Trump’s offer. The Grumman site had just been turned over to the town, he said. Mr. Trump’s housing proposal also came long before any of the controversial plans — like a ski mountain — that later plagued the site were introduced.

At the time, Mr. Cardinale said, Riverhead was also changing rapidly, swelling from a town of around 8,000 residents to a community with a population of more than 20,000. A project of that size would have been the single largest development in the town’s history and could have caused an even more dramatic population boom, Mr. Cardinale said.

Mr. Cardinale also noted that EPCAL was supposed to be devoted to economic development like commercial or industrial uses — something a housing development wouldn’t achieve.

“It would have truly changed the town and I’m not sure it wouldn’t have been for the better,” he said.

But Mr. Villella believes the town could have dodged many of the headaches it has since endured with EPCAL had it simply sold the property to Mr. Trump.

“It’s just ridiculous what’s been happening at that place,” Mr. Villella said. “I thought this was the greatest thing the town could have done.”

Mr. Villella said Mr. Trump’s one-time influx of cash would have filled the town’s coffers, while continuous tax revenue could have helped the town better weather the 2008 financial crisis.

“Believe me, we’d be in so much better shape now,” he said.

Mr. Trump wouldn’t make another play in the region until 2013, when representatives of the mogul met with Southold Town to discuss possible development on Plum Island, the site of a federal research facility that the federal government is moving forward with selling.

Supervisor Scott Russell said Mr. Trump pitched high-end condominiums and world-renowned golf courses for the island. The town immediately backed away.

“We had no interest in it,” Mr. Russell said. “We knew where we were going with it. We wanted to see the whole island preserved.”

Plum Island has been the site of a research facility since 1954, but that center is set to move to Kansas. The federal government intends to sell the island to the highest bidder, but in May, the U.S. House of Representatives passed a bill sponsored by Congressman Lee Zeldin (R-Shirley) banning the sale of the property.

Environmental advocates have long stressed the importance of the island, which they say is largely untouched by human activity and serves as a habitat for dozens of threatened species.

“The island has been allowed to regenerate and return to a natural state,” said Chris Cryder, special projects coordinator for Save The Sound. “You feel like you’re 1,000 miles away.”

Mr. Cryder said Plum Island is the largest haul-out for seals in the area and also supports more than 200 species of birds. Sea turtles, bats and rare tiger beetles also call Plum Island home, he said.

Many acres would have been destroyed to make room for a series of golf courses.

“You would have habitats that would be destroyed,” Mr. Cryder said. “It would forever change the characteristics of the habitats on that island.”

Mr. Russell said preservation was of high importance to the town, but also stressed the need for “good-paying jobs” associated with the research facility. Mr. Trump’s proposal would have provided a short-term boost, the supervisor said, but not the kind of long-term job solution the town needs.

“We’re looking to protect a significant number of jobs there,” Mr. Russell said.

Southold Town later passed zoning to prevent the kind of development Mr. Trump specializes in. Mr. Russell added that the town’s current road infrastructure wouldn’t have been able to handle such an influx of traffic, anyway.

But Mr. Cryder said “forward-thinking leadership” in the town couldn’t last forever and expressed concern another administration might be more open to development. He fears that a persistent developer could chip away at new administrations until the zoning laws are changed.

“Developers can sometimes outlast small towns and get what they desire,” he said.

Mr. Cryder said the federal government was supposed to conduct tours of Plum Island for prospective buyers this summer, but backed off — likely due to the recent House legislation. That bill hasn’t been passed by the Senate, he added, so developers are still waiting to see if Plum Island will go on the market.

“Donald is one of them,” Mr. Cryder said. “Nobody has officially backed out, so to speak. I don’t know what would happen if he became president, but he’s one of several developers who’s shown interest.”

Photo caption: Donald Trump, seen here speaking at the 2011 Conservative Political Action Conference in Washington, D.C., has made at least three pushes to develop the North Fork since 1999. (Credit: Gage Skidmore/Flickr)

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