Supreme Court “billionaire matchmaker” Leonard Leo, responsible for cementing the high court’s conservative majority, apparently flew a flag linked to the January 6th insurrection outside of his home in Maine. The report comes on the heels of a stunning New York Times investigation showing that Justice Samuel Alito — who Leo helped to confirm — flew the same ‘Appeal to Heaven’ flag outside of his vacation home, the second political symbol flown at Alito’s residences while the Court considered related cases.

Leonard Leo’s significant influence over the Supreme Court is deeply concerning. Not only is Leo exploiting his personal and financial relationships with Justices like Alito and Thomas in his role as Supreme Court billionaire matchmaker, but he also appears to share their total lack of respect for American democracy, the peaceful transfer of power, and checks and balances. Leo, these corrupt Justices, and our complicit Chief Justice Roberts must be held accountable for their efforts to undermine a core American institution for political gain.”

Accountable.US president Caroline Ciccone

The flag outside of Justice Alito’s New Jersey vacation home was the second insurrectionist symbol seen at one of his properties, with the other being an upside-down American flag, flown as an apparent “Stop the Steal” sign to protest the legitimate results of the 2020 election.

Leonard Leo and Justice Alito have been longtime allies. In 2005, as Alito faced a rocky confirmation battle, Leo took a leave of absence from the Federalist Society to help get him confirmed. On MSNBC, Sen. Sheldon Whitehouse (D-RI) noted that “the person responsible for the appointment of Justice Alito was Leonard Leo, the operative of the Koch brothers and creepy billionaires who have been meddling in the Court.” Leo has refused to comply with a subpoena issued by the Senate Judiciary Committee for his central role in the ethics crisis plaguing the Supreme Court.

More recently, a major ProPublica investigation found that Leo helped organize a luxury Alaskan vacation for Alito alongside hedge fund billionaire Paul Singer, who later had business before the court.

For more on Leo’s involvement in Supreme Court confirmations, visit


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