Just after 6 on the evening of Aug. 8, U.S. Sen. Susan Collins arrived outside a 7,900-square-foot Tudor-style mansion in the Mount Desert Island hamlet of Northeast Harbor. Across the street, a group of protesters held signs denouncing her for her role in confirming Brett Kavanaugh to the Supreme Court.

Inside, the man whom many credit with shepherding Kavanaugh and three of his conservative colleagues onto the court waited to welcome her to his new summer home – purchased to serve as a retreat for family and professional allies – and to commence a fundraising party for her re-election bid.

On an island that’s been a summer retreat for the rich and powerful since the days of John D. Rockefeller and Cornelius Vanderbilt, newcomer Leonard Leo is now perhaps the most influential seasonal resident of all. The executive vice president of the conservative Federalist Society, the 54-year-old attorney was until recently little known outside the Washington Beltway, where his private influence – he’s been called the “judge whisperer” – belied his low public profile.

That’s changed with the Trump administration and the elevation of two of Leo’s handpicked candidates to the Supreme Court, Neil Gorsuch in 2017 and Kavanaugh last October. He’s been the subject of an expose in the Los Angeles Times, an extensive profile in the New Yorker and, in May, an investigative report in The Washington Post that revealed his role in guiding a network of opaque nonprofits that raised $250 million from undisclosed donors and spent tens of millions in media campaigns to support President Trump’s Supreme Court nominees.

Federalist Society Executive Vice President Leonard Leo speaks at Trump Tower in New York in 2016. Associated Press

The New Yorker called Leo “in effect, Trump’s subcontractor” on Supreme Court nominations, on account of his having provided a list of Federalist Society-approved candidates dating back to the 2016 campaign. Conservative legal activist Ed Whelan has written that “no one has been more dedicated to the enterprise of building a Supreme Court that will overturn Roe v. Wade,” the decision that guarantees women’s right to terminate a pregnancy.

In October, Leo procured a base of operations in Maine, Edgecove, a 119-year-old mansion with 11 bedrooms and eight bathrooms, saying it would serve as “a retreat for our large family and for extending hospitality to our community of personal and professional friends and co-workers,” according to a statement he sent the Post.


Leo and his wife purchased the property for $3.3 million, $985,000 less than its appraised value, according to public records and real estate listings. The sellers were the heirs of chemical giant W.R. Grace chairman and CEO J. Peter Grace, who was the head of the U.S. branch of the Knights of Malta, a 971-year-old conservative Roman Catholic order to which Leo also belongs. Two months before the closing – which occurred at the height of the Senate debate over the Kavanaugh nomination – the Leos also paid off the mortgage on their primary home in McLean, Virgina, the Post reported on May 21.

“Leo is promising his allies that he’ll return the law to the pre-New Deal era, the robber baron era, and here he is managing to buy the cottage of one of the great robber barons,” says Lisa Graves, a former chief counsel on judicial nominations for the Senate Judiciary Committee and board president of the Center for Media and Democracy, a liberal-leaning government transparency watchdog group.


It’s not clear whether the Graces knew the Leos or whether the property was offered at a discount. Grace heirs Maryellen Mastrogiorgio, Patrick Grace and William Grace did not respond to interview requests made via the Maine attorney who organized holding companies they set up to handle the sale, Thomas Wheatley of Ellsworth. The Federalist Society’s spokesman, Peter Robbio of Creative Response Concepts, a public relations firm that served as media consultant to several of the Leo-linked nonprofits during their campaign to support Gorsuch’s nomination, did not respond to multiple requests for comment or an interview. (“He’s stepped away from his desk,” the receptionist at the firm said during one call.)

The families share ties to the Knights of Malta, the conservative order that ruled Malta for the 268 years preceding Napoleon Bonaparte’s conquest of the island and is now based in Rome, where it functions as a quasi-state, issuing its own passports, license plates, coins and postage stamps, occupying a seat at the United Nations, and maintaining embassies and full diplomatic recognition in 108 countries. It funds social, medical, and humanitarian projects around the world.

Leo has been a Knight of Malta since at least as early as 2004, when his membership was mentioned in a National Catholic Reporter profile occasioned by his appointment as head of Catholic outreach for the Republican National Committee. In the article, Leo said his job would be to “inspire and motivate Catholics to be an important part of the political process,” particularly around “nonnegotiable issues in the church (such as) abortion, marriage, cloning, and other culture of life issues like that.”


The Grace family and the W.R. Grace company have deep ties to the order. Their father, J. Peter Grace, chairman of W.R. Grace for 40 years until just before his death in 1995, was president of the knights in the United States. Their mother, Margaret Grace, a close adviser to influential Cardinal Leon Josef Suenens during the Second Vatican Council, was a member of the Dames of the Order of Malta from 1985 until her death in 2014, according to her obituary. At one point, eight members of W.R. Grace’s board of directors were knights.


The Collins fundraiser, the first known political event the Leos have held at Edgecove, came to light when an invited guest tipped off members of the progressive activist group Indivisible MDI, who decided to organize a protest.

Leonard Leo’s house in Northeast Harbor, which hosted a fundraiser this month for U.S. Sen. Susan Collins. Mount Desert Islander photo by Dick Broom

“We had opportunities to protest in front of private homes before, but it’s not something we normally do,” said Gail Leiser, a member of Indivisible MDI’s steering committee who helped lead the 20-person demonstration. “But given he’s the executive vice president of the Federalist Society, that puts him in a different realm than my neighbor down the street who wants to hold a fundraiser because she likes Susan Collins.”

Collins, Leiser said, had been elected as a moderate but was now allying with extreme conservatives. “The Federalist Society is not moderate and is not representative of Maine people and we think people need to be aware of that,” she said. “Collins, who sold herself as a moderate, is meeting with what many consider to be a radical right-wing part of the Republican Party.”

Collins had previously met Leo only once, at a lunch in the spring of this year, according to her campaign spokesman, Kevin Kelley. Federal campaign finance records show Leo donated $2,800 to her re-election effort on June 30, one of only seven candidates he gave to this year. It was his first-ever donation to the senator.


It is not clear whether Collins’ participation in the event indicates her philosophical agreement with the Federalist Society in regard to the ideal characteristics of federal judges: that they interpret the Constitution as the original framers of the 1780s did, a position that would dramatically roll back the scope of federal authority. Kelley would not respond to questions on this, instead providing a statement on the Aug. 8 protesters, whom he described as members of Mainers for Accountable Leadership, an activist organization that helped Indivisible promote the protest.

“MFAL is trying to turn this into some nefarious transaction, which is ironic because this is the very group that raised $2 million to try to buy Senator Collins’ vote,” Kelley wrote in a reference to crowdsourced funds raised during the Kavanaugh hearings to give to whomever challenged Collins in 2020, if the senator supported the nomination. “The fact is, Senator Collins’ votes are not for sale.”

Kelley said Collins had known the fundraiser’s co-organizer, former White House counsel and U.S. ambassador to the European Union Boyden Gray, for decades, and that about 20 people attended the event.

Donations from the event to Collins campaign will become public record on Oct. 15, when the next quarterly campaign finance reports are released.

Correction: This story was updated at 10:30 a.m. Monday, Aug. 19, 2019, to correct the spelling of Kevin Kelley’s name.

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