NORTHEAST HARBOR, ME (AP) — Caroline Pryor’s thoughts instantly wandered to Leonard Leo, who lives down the road, when Donald Trump was elected president earlier this month.
Leo has contributed more to conservative charities than most Americans. The then-unknown conservative lawyer started carrying out a plan years ago that has contributed to the transformation of Republican politics and U.S. courts. This effort culminated in Trump’s first term with the selection of three conservative justices to the Supreme Court.
Leo’s success lifted him out of the shadows and made him a villain to liberals and a hero to conservatives. However, the situation is more complex for his neighbors on a small island off the coast of Maine. In 2020, Leo and his family relocated to Mount Desert Island in search of a more private existence among the modest year-round inhabitants. It has not proved to be a haven.
In an area known for its peace, the conservatives’ presence has caused rifts despite their large local expenditures and charitable contributions to nonprofit organizations. Trump’s triumph has only increased that worry.
Pryor, a 65-year-old who has spent 40 years on the island, said it seems extremely personal. He arrives in a little, peaceful village in the country’s extreme northeast and carries out this sinister, extensive task that will have an impact on millions of people, yet all he wants is to live a quiet, anonymous existence.
Sheila Eddison protests in front of the home of Leonard Leo during the Mount Desert Island Marathon, Sunday, Oct. 20, 2024, in Northeast Harbor, Maine. (AP Photo/Robert F. Bukaty)
Image courtesy of Robert F. Bukaty/Associated Press
Protesters are drawn to Leo.
Two weeks prior to the election in November, those emotions were evident on a cool October morning. During the island’s annual marathon, Pryor and a dozen other individuals, largely women, gathered outside Leo’s estate to protest as sunlight flickered through the fading trees.
A comical life-size puppet of Leo, a rainbow arch for runners to cross, and blue and pink chalk with the words “You Are Amazing, Leonard Leo Is Not” scrawled across the street were among their supplies. While a boombox played Queen, Taylor Swift, and Dolly Parton, they rang cowbells.
One of the demonstrators, Mary Jane Schepers, encouraged runners to flip off Leo’s house, saying, “We are letting people on the island know who he is, and they might question taking his money.” They’re stealing money.
Answering a series of written questions, Leo stated that he had never given much consideration to whether his decision to relocate to the island would cause opposition.
Leo commented, “Even though I disagree with them and with some of their actions and statements, they are people who God created with worth and dignity, and their presence has been an invitation to pray for them.” He turned down a request for an interview.
Money causes a stir
Mount Desert Island is a picturesque island renowned for its rocky beauty, windswept beaches, and the renowned Acadia National Park. Leo, 59, and his family have been taking vacations there for decades.
He bought an 8,000-square-foot Tudor-style home in Northeast Harbor, one of the wealthiest villages on Mount Desert Island, for $3.3 million in 2018. On the island, some of the most powerful and affluent individuals in the nation, including billionaires like Mitchell Rales, celebrities like Martha Stewart, and scions like John D. Rockefeller Jr., have sought isolation and secrecy. As soon as Leo arrived, there was backlash. When he held a fundraiser for Republican Sen. Susan Collins the next year, protesters flocked to his house. When he was asked to present the then-president of a conservative think tank, The Heritage Foundation, at a nearby college, he quickly sparked further demonstrations, which caused the college to revoke the invitation.
After the conservative-led Supreme Court struck out the constitutional right to an abortion in 2022, the demonstrations intensified at the end of Trump’s first term.
Convincing Leo to leave was the activist’s original, ambitious goal. When that didn’t work, they focused on telling locals about the man living in the Tudor-style estate.
According to frequent protester Murray Ngoima, he thought he could come here and escape the unfavorable attention he receives for his political views. We’ve been successful in bringing his actions to light. And he has an issue with that.
Leo has been forced to increase security at his estate due to the protests. An altercation between a demonstrator and police in 2022 resulted in a lawsuit and a $62,500 compensation over First Amendment breaches.
“The activists have strengthened our conviction to be as active as possible in helping various institutions on the island,” Leo told The Associated Press, referring to his increased philanthropic contributions throughout the protests. For nearby NGOs, that has meant tens of thousands of dollars.
According to the trust’s annual giving report, which also named Leo as a member of the group’s executive committee, he and his wife, Sally, donated more than $50,000 in 2020 to the Island homes Trust, an organization that works to increase the supply of affordable homes on the island. Over the following three years, their gifts remained stable, placing them among the group’s top donors, according to trust documents. Additionally, Leo and his spouse were recognized as Mount Desert Island Hospital contributors. Additionally, the Leos have been named the Northeast Harbor Library’s regardonors.
Some locals don’t trust Leo’s donations.
Protesters have expressed suspicion over those gifts, calling on the organizations to return the funds and drawing comparisons to Leo’s use of them to sway Republican politics.
Susan Covino Buell, who lives on the island, described him as a wolf in sheep’s clothing. We cannot simply pretend that he is an ordinary member of our community.
When Leo became associated with the housing nonprofit, 75-year-old Buell resigned from her seat on the campaign committee. “I just felt it was so tainted,” Buell said, adding that she had attempted to persuade the group to turn down the funding.
A request for comment from the AP was not answered by the executive director of the trust.
Because of Leo’s involvement in removing federal safeguards for abortion, a group of anti-Leo activists also wrote an open letter demanding the hospital to return the money.
According to hospital spokesperson Mariah Cormier, the organization welcomes charity contributions that support enhancing the well-being and vitality of our neighborhood.
“People can judge for themselves why I do what I do,” Leo said, dismissing the notion that his donations were intended to purchase acceptance from a cynical community.
Not all of Leo’s charitable endeavors are contentious. Shop owners and service personnel face a dilemma as a result of his business at neighborhood establishments. Many claimed to disagree with Leo’s political views, but they depend on his funding to keep their businesses afloat, extending the hours that stores and eateries that used to close during the bitterly cold winter months.
Since Leo is such a delicate subject, several store owners refused to be questioned about the affluent conservative lawyer, stating that they did not want to sour their connection with him by bringing up the internal strife his business caused or how his opinions differed from their own.
As a devoted Roman Catholic, Leo has also influenced the island’s Catholic churches with money.
In 2023, the Roman Catholic Bishop of Portland sold St. Ignatius of Loyola Catholic Church in Northeast Harbor to the nonprofit Sacred Spaces Foundation, of which Leo is president and only member, for $2.65 million, according to county government documents. In the summer, when Northeast Harbor is at its busiest, the church now hosts one service per week.
His wife leads the music ministry at Holy Redeemer, a big stone sanctuary in Bar Harbor, where Leo regularly attends. According to locals, his presence has caused several longtime members to leave.
Eighty-year-old Lindy Stretch, who became a Catholic at Holy Redeemer more than ten years ago, left the congregation due to what she claimed was Leo’s increasing power within the church. Stretch remarked, “I simply couldn’t bear to watch that.”
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.
He won’t be leaving.
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 LeaderBilly Bob Faulkingham, who represents a district just off the island,excoriatedthe 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 websiteandover $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.
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AP researcher Rhonda Shafner in New York contributed to this report.
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