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NORTHEAST HARBOR, Maine — Following Donald Trump’s recent election as president, Caroline Pryor immediately thought of her neighbor, Leonard Leo, a prominent figure in conservative circles.
Leo, a conservative lawyer, has played a significant role in advancing right-wing ideologies in the U.S., particularly through a strategy that helped reshape the judicial landscape during Trump’s first term, including the appointment of three conservative justices to the Supreme Court.
As a result of his influence, Leo has emerged from anonymity, becoming a controversial figure; admired by conservatives and opposed by liberals. Yet, the reaction from residents on Mount Desert Island, where he lives, is more nuanced. Having relocated there in 2020 for a quieter life, Leo’s presence has stirred tension within the normally peaceful community, particularly in the wake of Trump’s electoral success.
“It feels deeply personal,” shared Pryor, who has been a resident of the island for forty years. “He comes to a small, quiet community in the far northeastern corner of the country and does this harmful work that impacts millions, yet he seeks to live an anonymous life here.”
The complexity of feelings surrounding Leo was evident during a protest held on a cool October morning, just weeks before the November elections.
With the backdrop of autumn leaves, Pryor and a group of about a dozen individuals—mostly women—gathered outside his home to demonstrate during the island’s annual marathon. They brought a life-sized puppet of Leo, a rainbow arch for the runners, and colorful chalk to create messages such as “You Are Amazing, Leonard Leo Is Not.” Amidst the sound of cowbells, their boombox played songs from notable artists like Dolly Parton and Taylor Swift.
“We aim to raise awareness about who he is in our community, which could lead others to reconsider taking his donations,” stated Mary Jane Schepers, one of the demonstrators. “They are accepting questionable money.”
In response to inquiries, Leo expressed that he had not anticipated any backlash from his move.
“While I disagree with their views and actions, they are individuals with dignity and worth,” Leo wrote, mentioning that their presence serves as a reminder to pray for them. He declined to engage in a face-to-face interview.
Leo, at 59 years old, has a long history of vacationing on Mount Desert Island, renowned for its scenic beauty and proximity to Acadia National Park. In 2018, he acquired an 8,000-square-foot Tudor-style home for $3.3 million in Northeast Harbor, an area populated by affluent individuals seeking a secluded lifestyle. Following his arrival, protests ensued, particularly during a fundraiser he hosted for Republican Senator Susan Collins.
Further protests erupted when Leo was set to speak at a nearby college, prompting the institution to withdraw the invitation due to backlash. The demonstrations intensified as Trump’s administration neared its end and after a conservative Supreme Court decision in 2022 that reversed federal abortion rights.
Initially, activists sought to get Leo to leave the island, but when that was unsuccessful, they pivoted to informing the local community about his affiliations. Murray Ngoima, a frequent protester, noted, “He believed he could come here to escape the negative attention tied to his politics, but we have succeeded in highlighting his actions.”
As a result of the protests, Leo has increased security around his residence, and a protester was arrested in 2022, leading to a lawsuit and a financial settlement related to First Amendment violations. Amid these tensions, Leo has ramped up his philanthropic efforts, claiming that the protests have motivated him to become more involved in supporting local organizations.
His notable contributions include over $50,000 to the Island Housing Trust, an initiative aimed at enhancing affordable housing on the island, and similar donations to other local nonprofits.
Despite this charitable involvement, skepticism persists among island residents. Some activists have encouraged these organizations to refuse Leo’s contributions, likening them to tactics meant to sway Republican politics. “He’s a wolf in sheep’s clothing,” stated resident Susan Covino Buell, expressing her disapproval.
The executive director of the housing trust did not respond to inquiries seeking comments. Additionally, anti-Leo campaigners have asked the local hospital to reject Leo’s donations, citing his role in diminishing federal abortion protections.
Mariah Cormier, a spokesperson for the hospital, defended the acceptance of donations, explaining they aim to enhance the health of the community.
Leo has rejected claims that his donations are attempts at generating goodwill within the community, maintaining that people can judge the true intentions of his actions. His presence extends to various local businesses, where a dilemma emerges for owners who may disagree with his political endeavors yet rely on his financial support to sustain their enterprises.
Even shopkeepers have refrained from speaking publicly about Leo, wary of jeopardizing their relationships with him. Leo’s influence also extends to local Catholic congregations, where his connections within the church are a source of controversy.
In a noteworthy transaction, Leo’s foundation purchased the St. Ignatius of Loyola Catholic Church in 2023. Meanwhile, he is a regular attendee at Holy Redeemer parish, where his wife leads the music ministry. Some long-standing members have distanced themselves from the church due to Leo’s perceived influence.
“I just couldn’t bear witnessing that,” remarked Lindy Stretch, who left the congregation after becoming uncomfortable with Leo’s role.
In response to concerns about declining attendance, Leo expressed gratitude for anyone who attends and is active in their faith.
Not all locals are opposed to Leo’s presence; some island Republicans have defended him amidst protests—House Republican Leader Billy Bob Faulkingham praised Leo for his steadfastness in supporting the causes he believes in.
Since his arrival in 2020, Leo’s financial network has reportedly contributed over $1 million to conservative initiatives in the state, further fueling opposition from his frequent protesters.
Despite the challenges they face, many from the October protest have lost track of the number of times they’ve gathered outside Leo’s estate. They have developed a routine, consistently standing in familiar spots, chanting slogans, and displaying their signs.
Although they acknowledge the difficulties ahead in driving Leo away, they take solace in making him feel uncomfortable. “He is thriving,” admitted Bo Greene, a participant who noted how nonprofits have utilized Leo’s contributions. “We might be a nuisance to him, but he continues to linger here.”
After the marathon ended and protesters cleared out, it appeared as though they had never been present—no trace of their chalk messages remained, as someone had washed it all away.
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