The Millionaires vs. the Mainstays: How the Haves Are Wreaking Havoc on the Have-Nots on Nantucket

Every summer, the quaint Massachusetts island of Nantucket experiences an influx of wealthy part-timers who flock to the elegant enclave to take up residence in their second (or third or fourth) homes.

The island comes alive with the hustle and bustle of summer fun as vacation-home owners and visitors alike descend, bringing with them a surge in local business, providing a boon to the island’s economy that helps to power it through the bitterly cold winter months.

However, behind the facade of crystal blue oceans, famed lobster rolls, and flower-lined streets, a bitter divide has formed between the moneyed summer tenants and the Massachusetts locals who call Nantucket home year-round.

Not only are there food and housing shortages on the island for many “mainstays” (the New York Times reports that some workers have had no choice but to live in their cars because 65% of the island’s nearly 12,000 housing units are occupied by seasonal residents), but lately, new intermillionaire territory wars seem to be heating up.

A new report sheds light on the growing tension between the island’s fair-weather inhabitants and year-round residents—raising questions about the actions of well-heeled summer tenants whom locals say make life harder for ordinary Massachusetts residents.

“Some of the well-off of Nantucket finally seem to be losing their minds—and much to the detriment of their neighbors,” said William D. Cohan in a recent news dispatch for Airmail.

Cohan, a native of Worcester, MA, who describes himself as suffering from “Billionaire Adjacent Syndrome,” made his way to Nantucket to report on this brewing war for the “Morning Meeting” podcast—affirming that, while income disparity has always been present on the island, it has reached desperate levels this year.

Into the woods

The past few years have seen bitter disputes erupt between homeowners over the trees on their properties—with several Nantucket residents accused of illegally cutting down neighbors’ greenery to improve their views or backyard aesthetics.

Most recently, Nantucket resident Jonathan Jacoby was accused of crossing his neighbor’s driveway and chopping down 16 mature cedar, cherry, and Leyland cypress trees while she was away from home.

His neighbor, Patricia Belford, claims that Jacoby destroyed her trees to improve his ocean view—noting that he later listed his property for nearly $10 million and claimed it offered “sweeping ocean views.”

She is suing Jacoby for $1.4 million in damages, and Jacoby is facing additional criminal charges of trespassing and felony vandalism. His trial is set to start on Sept. 15 in the Nantucket District Court.

Jacoby insists that he had permission; however, he told a Boston Globe reporter that he was merely “clearing out” his neighbor’s “crappy trees.”

“There seems to be an epidemic of people cutting down the trees in order to get that better view,” Cohan said on the “Billionaires Behaving Badly” episode of the “Morning Meeting” podcast. “This is at least the third tree-cutting incident in the last few years without permission or proper approval.”

The influencers invade

To make matters worse, the Instagram and TikTok influencer crowd is disrupting Nantucket’s local ecosystem, complicating life for residents who rely on summer income to sustain their businesses.

This situation came to a head recently when Kylie Swanson, a 36-year-old content creator from Oklahoma, signed a Nantucket rental lease in May 2025—and immediately began soliciting “freebies” from local businesses in exchange for social media exposure, according to the Wall Street Journal.

Though Swanson disputes asking for free services, she told the Journal that “it’s common in influencer culture to request discounts in exchange for collaboration.”

However, that kind of behavior from “washashores” (what newcomers such as Swanson and others who disrespect Nantucket’s social norms and core values have been called) threatens the locals’ very survival.

One business owner said she wasn’t offended by Swanson’s asks, but rather the influencer’s apparent ignorance about Nantucket’s delicate economy, which leaves business owners “10 weeks to make money” when the island is at its fullest.

Swanson perhaps added insult to injury when she told the outlet that, while she comes from “Oklahoma money,” the kind of wealth she grew up with is nothing compared to the fortunes of some of Nantucket’s richest residents—the majority of whom do not live there full time.

The bottom line is that while Swanson may have 82,300 followers on Instagram, she and other influencers are not necessarily helping the Nantucket locals—no matter how many artfully styled shots of hydrangeas they post.

Out with the old?

For part of the year, Nantucket is home to about 75 billionaires—a significant number, according to Cohan, given that there are “only roughly 900 billionaires in the country.”

“It’s quite something for nearly 10% of them to be concentrated on an island of only some 48 square miles,” he noted.

However, this massive concentration of wealth has created another problem for longtime residents: a growing demand for more luxury homes.

As a result, longtime Nantucket residents say they’re being pushed out by developers eager to convert even modest homes into high-priced properties. Those properties include a humble “fisherman’s shack” that was sold for $2 million just days after it was listed, and two plots of land the Nantucket Catholic Church sold to a summer resident for $4 million.

According to anonymous sources who spoke to Realtor.com®, one longtime local is locked in a legal battle with her billionaire neighbor, whom she accuses of encroaching on her land and trying to claim the parcel for himself.

One insider—who did not identify the parties involved in the dispute—alleged that the billionaire homeowner is attempting to “force [her] to leave” so he can “buy the land for cheap,” and that a fight between them will likely result in hefty legal fees that the woman cannot afford.

“He told her—via his attorneys—that he pretty much can afford to fight them forever,” the insider said, adding that, due to the ongoing litigation, the unnamed woman is unable to list her home and sell it at market value.

Another issue is that rising property values—driven by the influx of million-dollar homes—are pricing lifelong residents out of their own properties.

Nantucket has between 14,255 and 20,300 full-time residents, according to the U.S. Census Bureau and local studies. In summer, that number swells to 65,000 to 100,000, according to the New York Times.

“Developers built huge mansions nearby and then the town reassessed everyone,” says one Cape Cod real estate agent, who is working with Nantucket buyers considering a move back to the mainland after being priced out of their island homes.

“My client’s taxes are now $19,000 per year, and because her house value went up, her insurance company put a ‘bumper’ on her policy, and her insurance is now $15,000 per year—so she grew up there and should be retiring there but can’t afford to,” the listing agent explains.