NORTHEAST HARBOR, Maine — With Donald Trump’s recent election as president, Caroline Pryor couldn’t help but think of her neighbor, Leonard Leo.
Leo has played a significant role in promoting conservative agendas across the United States. Several years ago, this lesser-known conservative lawyer initiated a strategy that has substantially altered the American judiciary and the dynamics of the Republican Party. His influence peaked during Trump’s first term, leading to the appointment of three conservative justices to the Supreme Court.
This success catapulted Leo into the public eye, garnering him admiration from conservatives while simultaneously turning him into a controversial figure for liberals. However, for the residents of this tranquil island in Maine, the scenario is more complex.
Leo’s prominence and the considerable financial contributions he has made to local charities have created tensions within this tight-knit community. The residents’ unease has intensified in the wake of Trump’s electoral victory.
“It feels very personal,” remarked Pryor, a 65-year-old resident of the island.
Demonstrations against Leo recently took a visible form during an October morning, two weeks before the elections. As sunlight filtered through the autumn leaves, Pryor, accompanied by about a dozen others — mainly women — gathered in front of Leo’s estate.
Armed with a large puppet representing Leo, a rainbow arch for passing runners, and chalk in blue and pink, they wrote messages such as “You Are Amazing, Leonard Leo Is Not” on the road.
“We want to raise awareness among island residents about who he really is and encourage them to reconsider accepting his financial support,” stated Mary Jane Schepers, another protester, urging a group of runners to express their disapproval of Leo.
In his response, Leo mentioned, “While I disagree with them and with some of their actions, they are individuals created by God with inherent dignity and worth, and their presence is a chance to pray for them.” He opted not to engage in an interview.
Leo, 59, along with his family, has been a vacationer on Mount Desert Island for many years. He purchased a lavish Tudor-style home in Northeast Harbor for $3.3 million in 2018, further stirring discord within the area. The backlash intensified as his political influence became more pronounced, especially following the 2022 Supreme Court decision which rolled back abortion rights.
“He thought this place would provide a retreat from the scrutiny of his political activities,” observed regular protester Murray Ngoima.
In light of the protests, Leo expressed that they have merely solidified his and his family’s commitment to supporting various local organizations.
According to annual reports, Leo and his wife, Sally, contributed over $50,000 in 2020 to the Island Housing Trust, which aims to promote affordable housing. Their donations have continued over subsequent years, and they are also recognized as supporters of the local hospital and the Northeast Harbor Library.
Yet, their contributions have sparked skepticism, with some activists urging these organizations to reject Leo’s financial support, suggesting that he uses his donations to wield political influence.
“He is a wolf in sheep’s clothing,” accused Susan Covino Buell, a 75-year-old islander who relinquished her position on a housing nonprofit board upon learning of Leo’s involvement. The executive director of the trust did not provide a comment.
Protesters also sent an open letter to the local hospital, calling for a return of donations made by the Leos. A spokesperson for the hospital responded that their charitable donations foster the community’s health and well-being.
Leo dismissed allegations of attempting to purchase community acceptance with his donations, saying, “Those who have taken the time to get to truly know me can appreciate my intentions.”
The controversy surrounding Leo extends beyond his philanthropic efforts. His presence at local businesses places shopkeepers and service staff in a dilemma. While many disagree with his political stances, there is an acknowledgment of the necessity of his financial contributions to keep their businesses afloat.
Moreover, Leo has influenced the local Catholic church scene, purchasing St. Ignatius of Loyola Catholic Church for $2.65 million in 2023 through his organization, Sacred Spaces Foundation. Reports from residents indicate that his presence at the nearby Holy Redeemer church has discouraged some longtime congregants. When asked about the departing members, Leo remarked that he appreciates everyone who chooses to come to Holy Redeemer.
The situation isn’t entirely negative for Leo, however. Since 2020, he has channeled more than $1 million into conservative initiatives across the state. These include funding a conservative think tank and supporting a conservative state representative’s network with significant sums.
These donations have further heightened the resolve among his critics; even so, they recognize the challenge of dislodging him from the island.
“He is achieving what he set out to do,” acknowledged Bo Greene, a 63-year-old resident of Bar Harbor, referencing how organizations have accepted Leo’s contributions. “We may be making him uncomfortable, and he dislikes us, but he’s still very much a part of this community.”
