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Leonard Leo, an extraordinary matchmaker between judges and billionaires

FILE - The Supreme Court is seen on April 21, 2023, in Washington. (AP Photo/Alex Brandon, File)

Leonard Leo is not a household name in these United States, unless you reside in the household of a conservative billionaire or a justice of the U.S. Supreme Court (SCOTUS). Then you would be aware that Leo is one of the most influential individuals in the country, who has been remarkably successful in serving as a matchmaker between conservative justices and fabulously wealthy conservative Americans. He’s forged a convenient marriage of monetary power with judicial power.

Leo played an outsized role in the installation of the Supreme Court’s six-member conservative supermajority. He cut his teeth working for the appointment of Clarence Thomas. His strong support for all five of the other Republican appointees was instrumental in seating them. Leo also gets much credit for placing a tremendous number of ideologues on the various circuits of the U.S. appellate courts, particularly during the Trump presidency.

Leo was in a position to wield such influence because of the political and monetary resources he brought to the table as a shaker and mover in the conservative Federalist Society (Federalists). The group was founded by law school elites in 1982 for the purpose of infusing conservative philosophy into the judicial realm, and it has been wildly successful. In addition to the Supreme Court supermajority, all but eight of President Trump’s 51 picks for the courts of appeal were members of the Federalists. Most of those judges have been delivering conservative decisions, just as expected.

Of course, you don’t get that kind of clout in Washington without money, lots of money. The Federalists and Leo seem to have an inexhaustible supply of that corrupting commodity from conservative businesses and individuals. Between 2014 and 2017 alone, Leo collected more than $250 million in dark money for the Federalists and their affiliates. It was reported last year that a trust linked to Leo had been gifted $1.6 billion for his work, thanks to a Federalist contact.

This flow of cash has greased the wheels of Leo’s efforts to place judges on the federal bench who will see things much like his cadre of pro-business, anti-tax, ultra-conservative donors. Thus, we have seen the voting rights of minorities curtailed, America’s streets saturated with guns, mounds of dark money pouring into political campaigns across the country, chaos in red-state maternal care and voiding of curbs on greenhouse gas emissions, all to the great delight of those conservative donors.


Leonard Leo has used his rapport with members of the SCOTUS supermajority, and his access to the tremendous financial resources of Federalist donors, to make convenient matches that have benefited both sides. We have just learned of the interesting match that Leo appears to have facilitated between billionaire Paul Singer and Justice Samuel Alito. Singer treated Alito to an expensive fishing expedition, which the justice failed to disclose. Alito then failed to recuse himself from a number of cases in which Singer was interested. Alito could not see that he had done anything wrong, which is almost worse than taking the tainted largesse in the first place.

Leo also appears to have had a role in making the mutually-beneficial match between Justice Clarence Thomas and his billionaire friend Harlan Crow. Thomas received and failed to report a cascade of generosity from Crow, including lavish travel, and later failed to recuse on cases in which his benefactor was interested.

Leo has not overlooked other members of the SCOTUS majority, making perks available through affiliates, such as Scalia Law, George Mason University’s law school in Virginia, and other gatherings where the justices can rub elbows with conservative business titans.

Of course, the most troubling behavior has been engaged in by Thomas and Alito, the two longest-serving SCOTUS members, whose lifetime tenure seems to have given them a sense of entitlement. Their misbehavior provides a compelling case for SCOTUS term limits.

Having served 12 years on a state high court, I cannot comprehend how Alito and Thomas could really believe their behavior was anywhere close to being acceptable. My court was certainly nowhere near as exalted as SCOTUS, but the same basic ethical standards were applicable. Members of my court were prohibited by law from accepting pecuniary benefits from an interested party and, while there was no reporting requirement, every member of the court understood that such conduct was clearly inconsistent with judicial office. It simply did not happen.

The standard of recusal for my court was basically the same as that for SCOTUS. That is, recusal is called for in a case where one’s “impartiality might reasonably be questioned.” We have a procedure where anyone can lodge a complaint against any judge, including a high court justice, for an ethical infraction. If the complaint has substance, an investigation is initiated and the possibility of disciplinary action is available. SCOTUS sorely needs a similar mechanism, although it will never be initiated from the inside. It will take congressional action.

And, while Congress is at it, the kind of matchmaking Leo and his affiliates have been engaged in over the years should be carefully scrutinized to see what legislative action is necessary to curb the abuses. The rule of law in America depends upon it.

Jim Jones is a Vietnam combat veteran who served eight years as Idaho attorney general (1983-1991) and 12 years as a justice on the Idaho Supreme Court (2005-2017). He is a regular contributor to The Hill.