How Leonard Leo’s project to reshape US judiciary got its start in Wisconsin
In July 2015, Wisconsin’s supreme court shielded Governor Scott Walker, then a rising Republican star with aspirations to the presidency, from a criminal investigation.
The court’s conservative majority halted the investigation into what prosecutors suspected were campaign finance violations. One of the deciding votes was cast by Justice David Prosser, a conservative who had won re-election a few years earlier in a heavily contested race.
During the race, a state Republican operative said if their party lost Prosser, “the Walker agenda is toast,” according to an email included in a trove of documents the Guardian surfaced. Another vote for Walker came from Michael Gableman, a justice who had also waged a contentious campaign for his Wisconsin supreme court seat.
The high court, determining the prosecutors had overreached, ordered the investigation’s documents destroyed. But not before the Guardian got its hands on a copy. And buried in the 1,500 pages was a reference to a key figure in propelling Prosser and Gableman to victory: the co-chair of the right-leaning legal group the Federalist Society, organizer of dark money groups and conservative strategist Leonard Leo.
The Prosser and Gableman races were crucial skirmishes in Leo’s decades-long, ambitious effort to shape American law from the ground up. It’s a project whose full dimensions are only now becoming clear. ProPublica detailed the arc of Leo’s activism in a recent story and podcast with On The Media.
If Leo’s name sparks a note of recognition, it’s usually because he was Donald Trump’s judge whisperer and a leading figure in helping create the 6-3 conservative supermajority on the US supreme court. Leo realized decades ago it was not enough to have a majority of supreme court justices; he would have to approach the legal system holistically if he wanted to bring lasting change. To undo landmark rulings like Roe v Wade, Leo understood that he needed to make sure the court heard the right cases brought by the right people and heard by the right lower court judges.
Leo built a machine to achieve that goal. He helped ensure the nominations of justices from Clarence Thomas to Amy Coney Barrett. He used his closeness to the justices to attract donors to support his larger effort. He then used those donations to build a network of dark money groups supporting his candidates and causes across the US. And he helped elect or appoint state supreme court justices who were predisposed to push American jurisprudence to the right.
Wisconsin was where Leo honed his strategy. In 2008, in a racially charged challenge to the state’s first Black supreme court justice, Leo himself raised money for Gableman, according to a person familiar with the campaign. Leo passed along a list of wealthy donors with the instructions to “tell them Leonard told you to call,” this person said. All those people gave the maximum. Gableman won, the first time an incumbent had been unseated in Wisconsin in 40 years. (Leo declined to comment to us on his role in that race.)
Then in 2011, state GOP operatives turned to Leo to boost Prosser. They hoped he would help them raise $200,000 for “a coalition to maintain the Court”, the emails show. Prosser won, by half a percentage point. (When the emails mentioning his race surfaced, Prosser defended his independence.)
In 2016, Leo got involved again. Walker had a vacancy to fill and had three people on his shortlist: two court of appeals justices and the former attorney for an anti-abortion group and Federalist Society chapter head, Dan Kelly. “Leo stepped in and said it’s going to be Dan Kelly,” a person familiar with the selection told us. Walker denied speaking to Leo, who said he didn’t remember. From 2016 until the present, a group called the Judicial Crisis Network (which is now known as the Concord Fund), was a regular donor to state judicial races. Leo has no official role at the JCN, which as a dark money group does not have to disclose its donors. But he helped create and raise money for it, and JCN often works toward the same goals as the Federalist Society.
JCN was a crucial financial supporter of the public campaigns to win support for supreme court nominees backed by Leo, from Chief Justice John Roberts to Samuel Alito, Neil Gorsuch, Brett Kavanaugh and Coney Barrett. In Wisconsin, JCN sent increasing amounts of money to judicial races through circuitous routes. Sometimes the contribution flowed through a national political organization like the Republican State Leadership Committee. Other times, the money was sent to Wisconsin-based outfits.
Wisconsin is not the only state that Leo focused on. North Carolina shows the effects of more than a decade’s worth of big-dollar funding from his network and a torrent of negative ads questioning the integrity of the judiciary.
In 2022, after years of sustained campaign spending by the Judicial
Crisis Network and allied groups, North Carolina’s highest court flipped from a 4-3 Democratic majority to a 5-2 Republican majority. Months later, the court did something extraordinary: it reinstated a voter ID law that the same court, in its Democratic-led iteration, had found discriminated against Black voters. It also overturned a newly courtapproved elections map that had produced an electoral outcome reflecting the state’s partisan split.
In Wisconsin, the battles over the supreme court continue to be fierce. In April, Kelly, Leo’s chosen candidate, ran to maintain a conservative majority on the supreme court. It was the most expensive judicial race in US history, with both sides spending at least $51m. But Democrats were activated by the US supreme court’s ruling to overturn Roe and by election maps that had maintained Republican dominance in the legislature in a state evenly divided along partisan lines. Their candidate, Janet Protasiewicz, won resoundingly.
But that hasn’t stopped Republicans from trying to regain control. In September, there was talk of impeaching Protasiewicz because of comments