Background photo: Leonard Leo, then executive vice president of the Federalist Society, speaks to media at Trump Tower, Nov. 16, 2016, in New York (AP/Carolyn Kaster). Overlay: Examples of media coverage of Leo (NCR screenshots).
Northeast Harbor, Maine — December 3, 2024
When Donald Trump was elected president 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.
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 island resident.
Leo draws protesters
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.
"He is a wolf in sheep's clothing," said Susan Covino Buell, an island resident. Buell, 75, resigned her position on the nonprofit Island Housing Trust campaign committee when Leo got involved. The trust's executive director did not respond to a request for comment.
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.
"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.
In response to written questions, Leo responded: "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." He declined an interview request.
Money sparks controversy
Leo, 59, and his family have vacationed on Mount Desert Island for decades.
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. Backlash swiftly followed Leo's arrival. 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.
"He felt he could come here, and it would be a place to get away" from the negative attention for his politics, said Murray Ngoima, a regular protester.
Advertisement
Leo told AP that the protests have "strengthened our conviction to be as active as possible in helping various institutions on the island."
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. They made similar donations over the next three years, trustrecordsshow. Leo and his wife were also listed as donors to the Mount Desert Island Hospital. The Leos have also been listed as regulardonorsto theNortheast 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.
Leo 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.
"He is a wolf in sheep's clothing," said Susan Covino Buell, an island resident. Buell, 75, resigned her position on the housing nonprofit's campaign committee when Leo got involved. The trust's executive director did not respond to a request for comment.
Anti-Leo activists also penned an open letter urging the hospital to return the donation. 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 he and his wife were aimed at buying acceptance. "People who have taken the time to actually get to know me personally can judge for themselves why I do what I do," Leo wrote.
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.
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.
Leo is a regular at another parish, Holy Redeemer, a large stone sanctuary in Bar Harbor. His presence has driven off some longtime congregants, residents 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."
'He isn't going anywhere'
Not everyone is upset about Leo's Maine move.
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. Though energized, they have come to accept that 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."
Researcher Rhonda Shafner contributed from New York.
