BAR HARBOR, Maine — When Donald Trump was elected president earlier this month, Caroline Pryor’s mind turned immediately to the man who lives down the road — Leonard Leo.
Few people in America have done more to advance conservative causes than Leo. Years ago, the then-unknown conservative lawyer began executing a plan that has helped reshape the U.S. courts and Republican politics, an effort that culminated in Trump’s first term with the appointment of three conservative Supreme Court justices.
The success moved Leo out of the shadows, turning him into a hero to conservatives and a villain to liberals. But for his neighbors on a sparsely populated island off the coast of Maine, the equation is more complicated. Leo and his family moved to Mount Desert Island in 2020, seeking a relatively anonymous life among its unpretentious year-round residents. A refuge it has not turned out to be.
The conservative’s presence — despite significant charitable giving to local nonprofits and big spending locally — has generated fissures in a place known for tranquility. That anxiety has only spiked since Trump’s victory.
“It feels very personal,” said Pryor, a 65-year-old who has lived on the island for four decades. “He comes to a small quiet community in the very northeast corner of the country and does this evil, far-reaching work that is going to affect so many millions of people, but he wants to just live this anonymous, quiet life.”
Those feelings were on display on a brisk morning in October, just two weeks before November’s election. With sunlight flickering through the yellowing leaves, Pryor and a dozen other people — mostly women — gathered outside Leo’s estate to protest during the island’s annual marathon.
They came armed with a cartoonish life-sized puppet of Leo, a rainbow arch for runners to pass through and blue and pink chalk with which they scribbled slogans — “You Are Amazing, Leonard Leo Is Not” — across the road. They rang cowbells as a boombox blasted Dolly Parton, Taylor Swift and Queen.
“We are making people on the island aware of who he is, and they might question taking his money,” Mary Jane Schepers, one of the protesters, said as she urged runners to flip off Leo’s home. “They are taking dirty money."
Leo, in response to a series of written questions, said he “had never really thought about” whether his move to the island would spur opposition.
“While I disagree with them and with what some of them do and say, they are people created by God with dignity and worth and their presence has been an invitation to pray for them,” Leo wrote. He declined an interview request.
Leo, 59, and his family for decades have vacationed on Mount Desert Island, an idyllic island known for its rocky beauty, windswept beaches and the famed Acadia National Park.
In 2018, he purchased a $3.3 million, 8,000-square-foot Tudor-style estate in Northeast Harbor, one of Mount Desert Island’s wealthiest towns. Some of the country’s most influential and wealthy people — scions like John D. Rockefeller Jr., billionaires like Mitchell Rales and celebrities such as Martha Stewart — have sought privacy and anonymity on the island. Backlash swiftly followed Leo's arrival. The next year, protesters descended on his home as he hosted a fundraiser for Republican Sen. Susan Collins. He soon drew more protests when he was invited to introduce the then-president of The Heritage Foundation, a conservative think tank, at a nearby college, leading the institution to rescind the invitation.
The protests grew near the end of Trump’s first term and spiked after the conservative-dominated Supreme Court in 2022 overturned the constitutional right to abortion.
The activist’s initial goal was lofty: Convince Leo to leave. When that failed, they turned their focus to informing residents about the man in the Tudor-style mansion.
“He felt he could come here, and it would be a place to get away” from the negative attention he gets for his politics, said Murray Ngoima, a regular protester. “We have managed to draw attention to what he is doing. And that is a problem for him.”
The protests have compelled Leo to step up security at his estate. A protester was arrested in 2022, a confrontation with police that led to a lawsuit and $62,500 settlement over First Amendment violations.
Amid the protests, Leo has stepped up his charitable giving, telling The Associated Press that the activists have "strengthened our conviction to be as active as possible in helping various institutions on the island.” That has meant tens of thousands of dollars to local nonprofits.
He and his wife, Sally, gave over $50,000 in 2020 to the Island Housing Trust, an organization seeking to boost the amount of affordable housing on the island, according to the trust’s annual giving report that also listed Leo as a member of the group's leadership committee. They made similar donations over the next three years, trust records show, consistently ranking them among the group's top donors. Leo and his wife were also listed as donors to the Mount Desert Island Hospital. The Leos have also been listed as regular donors to the Northeast Harbor Library.
Those donations have raised suspicion, with protesters urging the groups to return the money and comparing the donations to the way Leo has used the money to influence Republican politics.
“He is a wolf in sheep’s clothing,” said Susan Covino Buell, an island resident. “We can’t just act like he is a regular person in our community.”
Buell, 75, resigned her position on the housing nonprofit's campaign committee when Leo got involved with the charity. She had tried to convince the nonprofit to reject the money “because I just felt it was so tainted,” Buell said.
The trust’s executive director did not respond to the AP’s request for comment.
A group of anti-Leo activists also penned an open letter urging the hospital to return the donation because of Leo’s role in ending federal abortion protections.
Mariah Cormier, a hospital spokesperson, said the institution accepts “charitable donations that aid in strengthening the health and vibrancy of our community."
Leo dismissed the idea his donations were aimed at buying acceptance from a skeptical community, saying people “can judge for themselves why I do what I do.”
It isn’t just Leo’s philanthropy that is controversial. His business at local establishments presents a quandary for shop owners and service workers. Many said they oppose Leo’s political positions, but they need his money to sustain their enterprises, allowing shops and restaurants that once closed during frigid winters to stay open longer.
Leo is such a sensitive topic that multiple shop owners declined to be interviewed about the wealthy conservative lawyer, explaining they did not want to damage their relationship with him by discussing how his views conflicted with their own and the internal conflict his business causes.
Leo, a devout Roman Catholic, has also used money to influence the island’s Catholic churches.
Sacred Spaces Foundation, a nonprofit that counts Leo as its president and sole member, purchased St. Ignatius of Loyola Catholic Church in Northeast Harbor for $2.65 million in 2023 from the Roman Catholic Bishop of Portland, according to records obtained from the county government. The church now holds one service a week during the summer, when Northeast Harbor is busiest.
Leo is a regular at another parish, Holy Redeemer, a large stone sanctuary in Bar Harbor where his wife is the head of the music ministry. His presence has driven off some longtime congregants, residents said.
Lindy Stretch, an 80-year-old who converted to Catholicism at Holy Redeemer over a decade ago, left the congregation because of what she said was Leo’s growing influence in the church. “I just couldn’t stand to watch that,” Stretch said.
Asked about people leaving the island church, Leo wrote he was “thankful for every person who takes the time to come to Holy Redeemer and is striving to be in union with the church and Christ, regardless of what they do or believe in their private lives.”
Not everyone is upset about Leo’s Maine move. Though the island's population is liberal — over 70% of residents voted against Trump in 2024 — Republicans in the state have come to Leo’s defense.
House Republican Leader Billy Bob Faulkingham, who represents a district just off the island, excoriated the protesters in an op-ed and heralded Leo in an interview for “sticking to his beliefs and donating to the causes he believes in.”
Since 2020, Leo’s network has funneled over $1 million to conservative causes in the state, including around $800,000 to a policy institute that funds a conservative website and over $300,000 to a conservative state representative’s political network.
Those donations have only deepened the opposition to Leo among his most frequent protesters, they said.
Most who gathered in October to protest during the marathon have lost count of how often they have met outside Leo’s estate. They have come so frequently they have a routine — each standing in the same place, chanting the same slogans and waving the same signs.
Though energized, they have come to accept they may never drive Leo from the island.
“He is succeeding,” admitted Bo Greene, a 63-year-old who lives in Bar Harbor, citing the way nonprofits have taken his money. “We are making him uncomfortable, and he hates us,” she said. “But he is still here.”
After the last marathoner had plodded by, the women collected their trash and packed away their puppet and signs before heading home.
A few hours later, it was like they had never even been there.
Not even their chalk slogans on the road remained: Someone had washed them away.
___
AP researcher Rhonda Shafner in New York contributed to this report.
