Did Leonard Leo Save Scott Walker?

Scott Walker speaking at the 833 East groundbreaking event in downtown Milwaukee in 2014. Photo by Jeramey Jannene.

The Federalist Society is known for promoting conservatives to positions as federal judges and U.S. Supreme Court justices. Its longtime leader Leonard Leo has gotten considerable press coverage recently for working behind the scenes to help Supreme Court Justice Clarence Thomas get financial help and luxurious vacations from wealthy conservatives.

But Leo has also gotten involved in state judicial races, and in Wisconsin he helped elect two conservative state Supreme Court justices who voted to shut down a criminal investigation of Gov. Scott Walker, as a recent story by Pro Publica documented.

In March 2011, a Republican operative warned that “the Walker agenda is toast” if conservative Supreme Court Justice David Prosser was not reelected in the April election, as emails later leaked to The Guardian revealed. The documents also showed that Leo was a key figure in making sure Prosser was reelected. And he also helped conservative Michael Gableman win election in 2008. Both justices would vote to kill a John Doe probe that targeted Walker.

Pro Publica reports that Leo was directly involved in raising money for the Gableman campaign, passing along a list of wealthy donors with the instructions to “tell them Leonard told you to call,” a source told the publication. “All those people gave the maximum. Gableman won, the first time an incumbent was unseated in Wisconsin in 40 years.”

Three years later “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.’ Prosser won, by half a percentage point.”

The criminal investigation that Gableman and Prosser would vote to shut down began with a probe of Walker’s successful 2010 campaign for governor. As County Executive Walker had a private email system that was used to hide the illegal campaigning on public time his staff was doing. Two of Walker’s staffers, Kelly Rindfleisch and Darlene Wink, were convicted of campaigning on public time to help elect Walker as governor. Four other aides were also convicted of violating campaign finance laws, along with other charges, in the John Doe probe. Records of the investigation showed that Walker’s staff used a separate Wi-Fi system, private email accounts and different laptops to evade scrutiny of their activities, and operated a private router just 20 feet from his office.

As investigators dug deeper they found Walker’s campaign continued to evade the law during his successful 2012 recall campaign by illegally coordinating his campaign with the supposedly “independent” Wisconsin Club for Growth. GOP operative R. J. Johnson ran Walker’s campaign while serving as chief consultant for the Wisconsin Club for Growth, and there were many emails showing Walker secretly fundraised for the Club for Growth, that his staff advised the governor to “stress that donations to” the Club for Growth “are not disclosed,” and detailing meetings Walker had with donors who soon contributed to Club for Growth, including a check to the club with a memo line saying the check was for Walker.

Had this evidence ever been presented in court, a judge might have found this laundering of money through the Club for Growth allowed Walker to evade campaign laws that restrict the amount of donations made and require disclosure of the names of candidates. If proven, this would show that Walker was running a campaign that illegally used untold amounts of dark money to help win election.

But a 4-3 decision of the Wisconsin Supreme Court, written by Gableman and supported by Prosser, voted to shut down the John Doe probe. Conservative Justice Patrick Crooks dissented, blasting the majority for ignoring past rulings by the U.S. Supreme Court as well as a recent Seventh Circuit Federal Court of Appeals ruling to “terminate a valid John Doe investigation in an unprecedented fashion.”

While Leo’s support of Gableman and Prosser helped lead to this decision, it’s important to note their most important backers: an incredible 76% of Prosser’s campaign support and 69% of Gableman’s campaign support came from the Club for Growth and Wisconsin Manufacturers and Commerce, two groups pushing for the decision to shut down the Doe probe, as Urban Milwaukee reported. Of course, a number of the donors to these groups were probably solicited by Leo and the Federalist Society. We’ll never know how many.

But Leo’s biggest impact may have been on two later Supreme Court races. In 2016, as Pro Publica reports, “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.”

At the time there was far more support for Mark Gundrum, a former Republican legislator who served alongside Walker in the state Assembly, helped write the state’s now-defunct ban on gay marriage and was a state appellate judge. “Forty-eight letters were sent to Walker on Gundrum’s behalf,” as the Wisconsin Law Journal reported at the time. “Of those, 19 came from trial-court judges throughout the state and 12 from members of the state Assembly. Also calling for Gundrum’s appointment were Jon Wilcox, a former justice, and the county executives of Waukesha and Manitowoc counties.”

But Leo had helped elect the two justices who saved Walker’s skin by killing the John Doe probe. Walker may have been so grateful that he let Leo pick the appointment. That turned out to be a huge mistake, as Kelly’s extreme views led to his defeat by Jill Karofsky in his bid for election in 2020 and then again in his comeback attempt in the 2023 election against Janet Protasiewicz. Those two elections helped tip the Wisconsin Supreme Court to a liberal majority. For that, it appears, Democrats have Leonard Leo to thank.