“I’m being very, very good with you today,” Dylan Eckardt said to me one recent morning as he careened his Range Rover around a curve off of Montauk Highway. We were headed to Gurney’s, the historically Wasp-ified hotel on the eastern tip of Long Island, when Eckardt had conceded to dispense with his habit of texting while driving. For the morning, anyway. Cops had already written him seven tickets in the last two months, he told me. “All the cops know who I am,” he said as he pulled into a parking lot and proceeded into an illegal spot. “No one is going to say shit to me.”

Eckardt, with his tousled, sun-streaked hair, has a reputation among the locals of Montauk. He is loudmouthed and wide-eyed, a former pro surfer and unofficial bouncer of the local surf beaches. But Eckardt had an epiphany a few years ago that he wasn’t going to make money forever off of riding waves. Instead, the Montauk native envisioned another wave breaking down upon the sleepy fisherman’s idyll where he grew up. Montauk had been lurching ever rapidly away from its lobster-shack roots as it began resembling the other hamlets of the Hamptons. Now there was a swell of Wall Street guys and Lululemon moms. People wore fedoras and drove Teslas. Montauk, the land of blue-collar fishermen, had become the province of nightclub promoters.

The locals were, of course, outraged. But Eckardt had a different response. He wanted to get in on the action. So he found a new calling—real estate—and joined Nest Seekers, the upscale boutique realtor, where he soon went into overdrive expediting the development of what remained of the quaint town. In his first four months, he brokered the deal for a Montauk establishment that had been on the block for half a decade and sold $10 million worth of property. Eddie Shapiro, the founder of Nest Seekers, told me that clients have described Eckardt as “totally nuts” and “an acquired taste.” But this is real estate, not social work, and only one thing matters. “They don’t know how he does it, but he does it,” Shapiro told me.

Real estate is a business built around who you know, after all, and no one has better connections around town than Eckardt—the man who says he is widely believed to be the inspiration for Cole Lockhart, Joshua Jackson’s character on The Affair. He’s in the water with town cops he went to high school with at dawn, he sweats on the elliptical at Gurney’s next to local contractors, and he rolls up to barbecues at the oceanfront homes of young tech billionaires, probably with a harem of pretty blondes who teach yoga and dance cardio classes, when the sun goes down.

“He has a different style. You’ll surf, and he’ll get everyone to be nice to you,” said Jon Krasner, a client and New York–based real-estate developer who has bought a handful of local mom-and-pop establishments to convert into hipper restaurants. “He’s got good at relationships. That doesn’t mean he’s good at underwriting deals, but that’s a huge advantage that these hedge-fund guys don’t realize. In these small-town communities, if they don’t want you to develop something there and you’re from Manhattan, you’re not developing something there.”

In some ways, Eckardt seems cognizant of this newfound status. After we arrived at Gurney’s, he walked out of the Range Rover and took a gander at the ocean rolling into shore before heading into the gym. “There’s nothing like me,” he said, tucking his shaggy hair behind his ears and maneuvering toward an elliptical machine. “I dress like a fashion kid from the city, I talk like an asshole, and I surf like a local. I’m the fucking rock star of real estate. I’m the fucking prince of Montauk.”

Montauk has a long history of frosty relations between wealthy carpetbaggers and the fishermen and surfers who live off the land. In the late 1920s, Carl Fisher built a yacht club that heralded the Astors and Vanderbilts and Morgans, at least until the Great Depression. Andy Warhol and Mick Jagger turned Montauk into an art scene in the 1970s, until Warhol died in the late 1980s. In those old days, at least, there seemed to be an intermingling between the disparate groups. Montauk was a place where cod fishermen, artists, waitresses, rock stars, deckhands, and an occasional billionaire in board shorts surfed together in the morning and drank beers together at night. “A drinking town with a fishing problem,” locals say, over and over.

Its latest colonizers, however, have taken less kindly to assimilation. As the Great Recession rippled across the East End, a number of hedge funders took advantage of a resort town in need of cash. Investor-backed hotels and nightspots tried to make a buck off one of the last affordable towns in the Hamptons at the most affordable time in a market dip, turning a laid-back surfer enclave into Williamsburg East. The success of restaurants like Surf Lodge and the Sloppy Tuna attracted more copycatting investors and nightclub promoters, and soon, the hamlet was transformed by rich twentysomethings in salmon pants and crop tops bopping from Sole East to Navy Beach to Ruschmeyer’s, leaving a trail of beer cans, loud music, and urine in their wake for locals to clean up.

Long Island Rail Road ridership catapulted up 34 percent two summers after Ruschmeyer’s and Sloppy Tuna opened their doors, and has continued to tick up since. New on-demand helicopter services that offered 30-minute trips straight to Montauk clubs for $600 a pop sold out, along with claustrophobic hotel rooms going for $800 a night. By the end of the 2015 summer season, the local police issued hundreds of violations. The Federal Railroad Administration investigated safety issues on the Long Island Rail Road, where hundreds of people stood between train cars each weekend to get out east.

“You’ve gotta pay your dues out there. Montauk is an old crowd. They hate these guys coming in here, and they’re going to fight them off like crazy. You really have to spend the first year kissing babies and shaking hands and showing people you’re on their side first,” said Krasner. “People don’t realize it’s a thriving town in the winter with a fire department and an elementary school and a softball team, and then people come in during the summer and pee on the streets. And you wonder why people hate the summer crowd?”

Hundreds of locals crowded into community board meetings with sandy feet and steam blowing out of their ears, calling on the East Hampton town to declare the party over in Montauk. “The people who live and work there are tightly bound together and they’re very protective of their community. Most people there believe that what’s happened over the last four, five years has been disrespectful,” Larry Cantwell, supervisor of the Town of East Hampton, whose district extends to Montauk, said. “The community spoke very loudly and clearly last summer that they had enough of it. They’ve gotten our attention and everyone else’s attention.”

Where locals saw mayhem, Eckardt saw an opportunity. The son of a fisherman and waitress, he and his two brothers would ride their bikes to the beach every morning before school to surf and catch 100 clams with their feet and feast on them for dinner. But less than two years ago, he returned from Malibu, low on cash, when he realized that his rustic, native background could provide him entrée into the town’s real-estate boom. A friend of a friend introduced him to Shapiro, who was looking for a guy in Montauk. Shapiro bought the Eckardt schtick immediately.

“The new multi-millionaire and even billionaire in that market has a McLaren in the garage, but they wear baseball hats, flip-flops, and drive pickup trucks. A lot of these guys can relate to him. They feel it’s more authentic, as opposed to someone who’s wearing the Hamptons’ Ralph Lauren outfit with the perfect hair who makes you feel like you’re being buttered up from the start,” Shapiro said. In a town where Shapiro said a property on one side of the street can be worth $2 million and across the road, $600,000, the block-by-block knowledge Eckardt has from combing those streets his whole life matters. “He’ll come in and tell you, ‘That’s not the street you want to be on.’”

When Eckardt was brought in to broker the deal to sell Trail’s End, the Montauk establishment that was once won in a card game in 1927, he saw an opportunity to blend a bit of the old Montauk with the inescapable newness that money would provide. With its neon sign and popcorn walls, Trail’s End is the real deal among a smattering of new restaurants painstakingly manufactured to look authentic. He brokered the deal between Robert Rottach, who ran the place with his family for three decades, and Michael Nasti, a Long Island businessman who’s been coming out to Montauk for more than 20 years. He hooked Nasti up with a local chef and brought in his former partner Anna Cappelen to do the interior design. Nasti has no plans to turn it into the next Surf Lodge—there will be no D.J., no line out the door at 11 P.M., and he will keep the restaurant open 12 months a year, so it will serve the community, not just the throngs of summer tourists. Cappelen is keeping the neon sign and the original mahogany bar inside.

“My mom used to waitress there three decades ago, when I was five years old,” Eckardt said. “I know the vibe and I’m keeping it. I’m a local and all the locals know me because I’ve either slept with their daughters or played football with their sons, and they know I’d never put in shit that wouldn’t work.”

Five years ago, anyone talking about making it in Montauk would have gone on and on about the rich kids of Instagram and a Vegas Strip–ification of a beach town. But now a new set of buzzwords seems to be on the tip of every broker’s tongue. It’s all about the authenticity, at least the kind you can fabricate, by getting back to the old Montauk.

These days, everyone is so over 22-year-olds in pink pants bumping into them and spilling their drinks. Indeed, Montauk is turning into a place for families; now, that’s what’s cool, they say. Part of this shift has to do with the locals enforcing their own rules and putting their feet down. Also, a lot of these guys who started developing Montauk a half decade ago are now in their 30s with families of their own and they don’t, in fact, want to be out partying with sloppy messes.

What they’re searching for is the Montauk vibe of their collective memories—the soul that the Surf Lodge and Ruschmeyer’s sold for a quick buck, landing Montauk a Vogue cover in the process. The next wave for Montauk is not dissimilar from what happened with Brooklyn a decade ago, when a bunch of deep-pocketed, pitiless authenticity-suckers colonized the outer borough. They kicked out enough mom-and-pops and obscured enough brownstones with glass condos just before they realized they actually needed those mom-and-pops and brownstones to sell the scruffy-bearded, artisanal-made, Lena Dunham–ized vision of Brooklyn Manhattanites wanted to buy. If the newest round of developers in Montauk have a say, they will keep the town the most authentic version of an inauthentic version of itself.

It just so happens that that’s what Eckardt has in mind. He is working with an investor to redevelop a prominent, rundown motel at the center of town and turn it into a family-first getaway. There will be no late live music or bar or trendy restaurant—just a little food stand that sells lobster rolls next to the outdoor movie screen that will show old movies like The Sandlot for kids at night. Each room will have a surfboard. His brother is doing the landscaping and they are letting the owner operate for another season before they close the deal so he can walk away with a full summer’s worth of income in his pocket.

“We’re not doing anything like Surf Lodge. It’s 100 percent not a party. I would never let that happen,” he said. “I would firebomb Surf Lodge before I let that happen.”

He is working with another developer to buy up dozens of cottages around town, often a few of them grouped together on mini-compounds, that they will renovate and rent out to families for weeks at a time. They are not building new structures or developing anything that doesn’t already exist. He has been combing through woods he walked through as a kid—where he remembered seeing tiny dilapidated houses—and putting offers in on behalf of his clients for those existing structures that someone has already let die. The idea is that they will breathe life back into them, make a quick buck for locals and for themselves once they re-do them, and deliver an authentically Montauk experience to people who want in on the action.

“People don’t like hotels anymore. They want a little house where they can come back to every year,” he said.

The locals—for now—have no problem with this. “Re-investment in properties is a good thing. When property values are increasing and existing owners sell and a new owner comes in and upgrades it and upscales it, that’s a positive for the economy,” Cantwell said. “If someone buys a motel, continues to invest money in the property, and makes it a more valuable asset, we encourage that.”

After years of tumult between the old and new, Montauk could have a worse steward than Dylan Eckardt. “When I came back to town, Montauk was trendy and I saw an opportunity,” he said, driving by some of the cottages he has offers out on. “I saw you don’t have to be a fisherman or a construction worker or a waitress. People never told us that we could be something like a real-estate agent or a banker or a lawyer when we were kids. No one I knew did that.”

There is the chance for him to make real money on these projects, sure, but he said he often chooses to roll over his commission into equity, so he has a say in how a project turns out, and he can pump the brakes if it starts heading in a direction he doesn’t see as a fit for the town. “I want something better for my town. There’s nothing wrong with wanting something better,” he said.

Perhaps that’s why he bought a 1967 Continental convertible with suicide doors. He took it out for a ride around town when it arrived in Montauk last month on a sunny May afternoon when the brakes failed. He couldn’t stop the car and a Range Rover smashed into him from behind. He walked away without a scratch, and after the car is fixed, he is having it finished with a fresh coat of matte black paint. “Can you believe a fucking Range Rover hit me? Since when did this town become all Range Rovers?”