When Donald Trump became president, Caroline Pryor, a longtime resident of a peaceful island in Maine, couldn’t help but think about her neighbor Leonard Leo.
Leo isn’t just any neighbor. He’s a major force behind shaping conservative politics and the U.S. courts, including helping Trump appoint three conservative Supreme Court justices. This made him a hero to some and a villain to others.
In 2020, Leo moved with his family to Mount Desert Island, a beautiful, quiet place with rocky shores and Acadia National Park. The island is home to both year-round residents and wealthy vacationers like Martha Stewart and the Rockefellers. Leo hoped for a low-key life here, but things didn’t go as planned.
A Warm Welcome? Not Exactly.
Leo’s presence has caused quite a stir. Despite donating generously to local charities and businesses, many residents are uneasy. Some see his contributions as a way to “buy” acceptance, given his role in overturning federal abortion rights and influencing Republican politics.
Caroline Pryor, who’s lived on the island for 40 years, put it bluntly: “He does this far-reaching work that affects millions, but here, he wants to just live quietly. It feels personal.”
Protests against Leo began shortly after his arrival. One group even set up outside his house during a local marathon, bringing signs, music, and a giant puppet of Leo. They chalked messages like “You Are Amazing, Leonard Leo Is Not” on the road.
Their goal? To let people know who Leo is and to discourage others from accepting his money.
Leo’s Response
Leo, a devout Catholic, has taken the protests in stride, saying they’ve motivated him to give back even more to the community. He’s donated over $50,000 to the Island Housing Trust for affordable housing and has supported the local library and hospital.
But not everyone is impressed. Some residents, like Susan Buell, resigned from committees tied to Leo’s donations, calling the money “tainted.” Others worry his influence might creep into local institutions, like the Catholic churches on the island.
Leo denies that his donations are about gaining acceptance. “People can judge for themselves why I do what I do,” he said.
Local Businesses and Tensions
Leo’s spending at shops and restaurants has created a dilemma for local business owners. While they appreciate his business, some disagree with his politics. Many declined to comment publicly, fearing it could hurt their relationship with him.
His presence has also caused ripples in the local Catholic community. One church he’s involved with now holds just one service a week, and some parishioners have left altogether, saying his influence makes them uncomfortable.
Protesters Keep Going
The protests haven’t let up. Activists frequently gather outside Leo’s estate, waving signs and chanting slogans. They admit they’re unlikely to convince him to leave, but they feel their efforts are worth it.
“We’ve made him uncomfortable,” said Bo Greene, another protester. “But he’s still here.”
Despite their efforts, Leo isn’t budging. He continues to live on the island, donate to local causes, and stick to his beliefs. For now, the protests and tensions remain part of life on this quiet Maine island, where even chalked slogans don’t last long before they’re washed away.