John Roberts Bought an Island House With No Ferry, His Rulings and His Wife’s Money Are Catching Up With Him

Along this remote stretch of the Maine coast, where every day looks like a picture made of light and water, the Chief Justice of the United States is simply “John” to many people. John, who has spent more than 20 summers on Hupper Island, a retreat about 90 miles northeast of Portland, with no cars and barely 2 dozen houses. John, who trades favors with neighbors and takes their teasing about his boating skills. And John, who sat on the dock in Port Clyde that morning, across from the island, with coffee and a cinnamon roll.

For a long time, his life here was a succession of stews and easy friendships, as more than 2 dozen residents described it one summer. In recent years, the Supreme Court has turned Americans’ lives upside down and handed President Trump more and more power. As the rulings piled up, so did a very personal anger here toward the man who helped make them possible.

His summer retreat has become a battleground. Neighbors take to the water and call themselves “kayak-tivists,” forming flotillas in front of his island home and holding up waterproof signs. A local columnist suggested giving him the middle finger. Even old friends who would never join the paddlers are pulling away out of grief over his decisions, especially the 2024 ruling that gave the president broad immunity from criminal prosecution. Today, far more security personnel surround him than before.

This little world shows how controversial rulings and collapsing trust have made the justices lonelier than ever. The growing danger to public officials adds its own weight. “The way I see it, the barrier goes both ways,” said Mary Anne Mason, a friend and former law partner who lives in Port Clyde. It has become harder for him to approach people, she said, and just as hard for them to approach him. The peninsula is split over whether a judge should be made to feel the public’s anger or left alone because his office is supposed to be immune to pressure. For the protesters, the hour is too serious for those niceties. Lifetime-appointed judges, they say, leave citizens no other option.

Roberts bought the gray, shingled house on the water in 2006, the year after he rose to the top of the Court. The place says one thing unmistakably: away from Washington. The island can only be reached by private boat, no ferry, no bridge. From early July through early October, he stepped into another world, among wealthy summer residents and local lobster fishermen, Democrats and Republicans alike. His former law partner Kevin Lipson, who has been here for 40 years, brought him to the island and found the house. There was an unwritten rule not to talk to him about the Court. If a stranger asked what he did for a living, he simply said he was a judge. Despite strong reactions to some rulings, from eliminating limits on campaign spending to saving Barack Obama’s health care law, many people saw him as a trustworthy, reasonable man, a defender of the Constitution.

The first crack came after the abortion ruling, with a column by Becca Shaw Glaser in the now-defunct local newspaper in 2022. A gardener and activist from this coast, she wrote that she could no longer stand watching her state welcome a justice who had gutted the Voting Rights Act and voted against a constitutional right to same-sex marriage. That summer, she wrote, he had also backed Dobbs v. Jackson, the ruling that ended the federal right to abortion. If people saw him walk into a store, she urged them to tell him what they thought of him and his “illegitimate, arch-conservative court.” “Yell, boo, whisper,” she wrote, give him a thumbs-down or the finger, refuse him service. She also recommended boat protests outside his house. “He might see you.”

His position in Dobbs had actually been more nuanced, a lonely and unsuccessful attempt to preserve the right through the 15th week. He still voted with the majority, led the Court, and she held him responsible. Letters to the editor split sharply, with many accusing her of inciting violence. Shaw Glaser soon lost her column, and the newspaper apologized to the justice. Then others followed her. New letters were outraged at the way she had been treated, and stickers appeared: “Roe, Roe, Roe Your Vote.”

2 years later, the Court granted Trump sweeping immunity for actions taken in office before the January 6, 2021 attack on the Capitol. Roberts wrote the majority opinion. While Trump pushed the boundaries of the Constitution, the Court waved through many of his actions, formally temporary and yet still a remaking of the state. Nobody knew Roberts’ true voting record because so much ran through the secretive emergency docket, where decisions often come without a vote count and often without an explanation. He had long been willing to give the president more power. Maine had voted against Trump twice, and many neighbors found Roberts painfully hesitant whenever it came to standing up to the president.

The protests on the water began the year before and have now become part of the scenery. Twice each summer, 2 rows form, kayaks with paddles hooked together just off his house, people standing on the dock behind them. There were never more than a few dozen, but the message traveled far. An artist built cardboard kangaroos after the phrase “kangaroo court” and named them after the conservative justices. Signs stand along the roads: “Roberts benched the Constitution,” and: “Mainers against the Roberts agenda.” One morning in September, written across an intersection in colorful chalk were the words “Equal Justice Under Law,” the phrase carved into the front of the Court.

Roberts stayed silent. As Chief Justice, he speaks almost entirely through written opinions and seems distant to those who are furious with him. Once, the protesters encountered another member of his household. After a rally in August 2025, a young woman approached them and asked what they hoped to accomplish and whether they had thought about his wife and children. She said she was Josephine Roberts, 25, the justice’s daughter. Her father was not even home, she said, he respected her own left-wing views and was a wonderful father. Shaw Glaser, still appalled by the rulings, later wrote down a feeling of sympathy for the daughter.

Her name has appeared in our reporting before. We have been digging into this matter again for months. As a headhunter for elite law firms, Jane Roberts brought home $10.32 million in commissions. The money came from companies and law firms, some of them with active cases before the Court her husband presides over. Marriage may separate the bank accounts, but it does not separate the worlds. A judge is supposed to decide cases as though he does not know the parties, while at the kitchen table the bills from that very same world are coming in. You do not need distrust to stop and stare at that, arithmetic is enough. Independence is not a title you wear, it is a distance you keep. Between the bench and this family’s commissions, that distance was never longer than a hallway.

This summer, Jane Roberts invited the Port Clyde cigar club over, saying everyone was welcome. But the season was boiling, with a Senate race and, in July, the killing of a 25-year-old Colombian delivery driver by immigration officers south of Portland. Approval of the Supreme Court fell to a historic low of 33 percent in one poll. At the dock, Lipson walked up to Ellen Koches as she was fastening a sign. “I’m taking a picture of your license plate, I’m going to find out where you live, and I’m going to protest outside your house,” he said. “Is that a threat?” It was a promise, he replied. A federal law prohibits demonstrations outside judges’ homes, though it is rarely enforced, and legal scholar Timothy Zick called protesting from the water an open legal question.

The Roberts Court: Citizens United, gutting the SEC, severely weakening the EPA, deportation without due process, weakening organized labor, and expanding presidential immunity.

Roberts pulled back. After growing threats against public officials, including an attempted attack on Justice Brett Kavanaugh in 2022, security was tightened. On Sundays after church, he stopped lingering at the dock. The change was hard to watch, said Tamara Cody, an old friend. The Court had long since stopped taking a summer break and struck down Trump’s attempt to change the rules for mail-in voting. In August, Roberts wrote a rare, sharp dissent against the reconstruction of the White House ballroom. On Independence Day, though, he celebrated with around 60 neighbors on a lawn, with a rabbi’s blessing and “God Bless America.”

Wendy Schlotterbeck, who had been spending summers here since before there were docks or electricity, could not stand the sight of him celebrating. His Court had just cut protections for transgender athletes and minors and allowed Trump’s immigration crackdown to go forward. 3 of her relatives are trans, friends had been arrested. She would have liked to look him in the eye and ask whether he knew what his rulings were doing to her family. Instead, she left. The next morning, she paddled in front of his house for the first time, a sign in her hand, “Justice for All,” hoping he would see it. A lifetime appointment puts the man beyond the reach of any election, the island beyond the reach of the town. What remains is a neighbor in a kayak whom he can overlook from the shore