Trump’s Court Whisperer Had a State Judicial Strategy. Its Full Extent Only Became Clear Years Later

In July 2015, Wisconsin’s Supreme Court shielded Gov. Scott Walker, then a rising Republican star with aspirations to the presidency, from a criminal investigation.

The court’s conservative majority halted the probe into what prosecutors suspected were campaign finance violations. One of the deciding votes was cast by Justice David Prosser, a conservative who had won reelection a few years earlier in a heavily contested race. During the race, a state GOP 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 both 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 decadeslong, 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 U.S. 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 U.S. 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 was unseated in Wisconsin in 40 years. (Leo declined to comment to us on his role in that race.)…