NORTHEAST HARBOR, Maine (AP) 鈥� When Donald Trump was earlier this month, Caroline Pryor鈥檚 mind turned immediately to the man who lives down the road 鈥� 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 , an effort that culminated in Trump鈥檚 first term with the .
The success moved Leo out of the shadows, turning him into a hero to conservatives and . 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鈥檚 presence 鈥� despite significant charitable giving to local nonprofits and big spending locally 鈥� has generated fissures in a place known for tranquility. That anxiety has only spiked since Trump鈥檚 victory.
鈥淚t feels very personal,鈥� said Pryor, a 65-year-old who has lived on the island for four decades. 鈥淗e 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.鈥�
Leo draws protesters
Those feelings were on display on a brisk morning in October, just two weeks before November鈥檚 election. With sunlight flickering through the yellowing leaves, Pryor and a dozen other people 鈥� mostly women 鈥� gathered outside Leo鈥檚 estate to protest during the island鈥檚 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 鈥� 鈥淵ou Are Amazing, Leonard Leo Is Not鈥� 鈥� across the road. They rang cowbells as a boombox blasted Dolly Parton, Taylor Swift and Queen.
鈥淲e are making people on the island aware of who he is, and they might question taking his money,鈥� Mary Jane Schepers, one of the protesters, said as she urged runners to flip off Leo鈥檚 home. 鈥淭hey are taking dirty money."
Leo, in response to a series of written questions, said he 鈥渉ad never really thought about鈥� whether his move to the island would spur opposition.
鈥淲hile 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,鈥� Leo wrote. He declined an interview request.
Money sparks controversy
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 a $3.3 million, 8,000-square-foot Tudor-style estate in Northeast Harbor, one of Mount Desert Island鈥檚 wealthiest towns. Some of the country鈥檚 most influential and wealthy people 鈥� scions like , billionaires like and celebrities such as 鈥� have sought privacy and anonymity on the island. Backlash swiftly followed Leo's arrival. The next year, 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 the invitation.
The protests grew near the end of Trump鈥檚 first term and spiked after the conservative-dominated Supreme Court in 2022 overturned the constitutional right to abortion.
The activist鈥檚 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.
鈥淗e felt he could come here, and it would be a place to get away鈥� from the negative attention he gets for his politics, said Murray Ngoima, a regular protester. 鈥淲e have managed to draw attention to what he is doing. And that is a problem for him.鈥�
The protests have compelled Leo to step up security at his estate. A protester was in 2022, a confrontation with police that led to 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.鈥� 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 that also listed Leo as a member of the group's leadership committee. They made similar donations over the next three years, , consistently ranking them among the group's top donors. Leo and his wife were also as donors to the Mount Desert Island Hospital. The Leos have also been listed as .
Some residents are suspicious of Leo's donations
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.
鈥淗e is a wolf in sheep鈥檚 clothing,鈥� said Susan Covino Buell, an island resident. 鈥淲e can鈥檛 just act like he is a regular person in our community.鈥�
Buell, 75, 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 鈥渂ecause I just felt it was so tainted,鈥� Buell said.
The trust鈥檚 executive director did not respond to the AP鈥檚 request for comment.
A group of anti-Leo activists also urging the hospital to return the donation because of Leo鈥檚 role in ending federal abortion protections.
Mariah Cormier, a hospital spokesperson, said the institution accepts 鈥渃haritable 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 鈥渃an judge for themselves why I do what I do.鈥�
It isn鈥檛 just Leo鈥檚 philanthropy that is controversial. His business at local establishments presents a quandary for shop owners and service workers. Many said they oppose Leo鈥檚 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鈥檚 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 , 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鈥檚 growing influence in the church. 鈥淚 just couldn鈥檛 stand to watch that,鈥� Stretch said.
Asked about people leaving the island church, Leo wrote he was 鈥渢hankful 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.鈥�
鈥橦e isn鈥檛 going anywhere鈥�
Not everyone is upset about Leo鈥檚 Maine move. Though the island's population is liberal 鈥� over 70% of residents voted against Trump in 2024 鈥� Republicans in the state have come to Leo鈥檚 defense.
House Republican Leader , who represents a district just off the island, the protesters in an op-ed and heralded Leo in an interview for 鈥渟ticking to his beliefs and donating to the causes he believes in.鈥�
Since 2020, Leo鈥檚 network has funneled over $1 million to conservative causes in the state, including around and .
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鈥檚 estate. They have come so frequently they have a routine 鈥� 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.
鈥淗e is succeeding,鈥� admitted Bo Greene, a 63-year-old who lives in Bar Harbor, citing the way nonprofits have taken his money. 鈥淲e are making him uncomfortable, and he hates us,鈥� she said. 鈥淏ut he is still here.鈥�
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.
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AP researcher Rhonda Shafner in New York contributed to this report.
Dan Merica, The Associated Press
