Kellyanne Conway, Leonard Leo, and the Quiet Supreme Court Jockeying Under Trump

It was a good deal for Kellyanne Conway. Not only did the former White House counselor likely rake in millions when she sold her polling firm in 2017 — she also got congressional investigators, who had raised conflict of interest concerns about her continued ownership of the company, off her back. But it may have been an even better deal for Leonard Leo, the conservative activist who appears to have secretly facilitated the move. 

According to Politico, which first reported the transaction, Leo seems to have used one of his dark money groups to finance the sale of the Polling Company, which Conway founded in 1995, to Creative Response Concepts Inc., a conservative public relations firm he now co-owns — at the same time she was promoting his preferred Supreme Court picks to Donald Trump. The deal may constitute a violation of ethics laws, experts told the outlet. It also shines a light on how Leo, a former vice president of the Federalist Society and a current co-chair of its board of directors, has wielded outsize influence over the judiciary’s rightward shift — possibly through shady means. “It really shows Kellyanne as a vehicle for Leo, the leading role Leo has played, and how Trump became his instrument,” Bruce Freed, president of the nonpartisan Center for Political Accountability, told Politico of the transaction. 

The timing of the deal was convenient for both Conway and Leo. Conway was facing pressure to unload the company because of her government post. But without her involvement in the firm, it was unclear how much it was actually worth, even as she valued it between one and five million dollars. According to Accountable.US, a watchdog group that alerted Politico to the financial records, Conway netted more than $2.5 million in the deal in the end.

Meanwhile, Conway was also a cheerleader for his list of Supreme Court candidates, including Neil Gorsuch and Amy Coney Barrett, both of whom were nominated to the court by Trump and confirmed by the Republican-led Senate. It’s not clear if the deal or her longtime association with Leo factored into her promoting the picks to Trump, nor is it clear her lobbying was even necessary; as conservative legal expert Paul Whelan told Politico, Trump had already made a “clear and high-profile commitment” to filling any Supreme Court vacancies with Federalist Society-approved judges. But the dealings between Leo and Conway do raise significant ethical and legal concerns — and provide a window into his efforts to swing the judiciary to the right. 

Other than Mitch McConnell, there is perhaps no one more responsible for that rightward shift than Leo. He helped get Clarence Thomas confirmed to the bench under George H.W. Bush. He helped Samuel Alito and John Roberts get confirmed during the George W. Bush presidency. And, after helping McConnell block Merrick Garland’s proceedings under Barack Obama, he worked to install Gorsuch, Barrett, and Brett Kavanaugh during Trump’s presidency — helping to lock in a Supreme Court supermajority for decades to come, potentially.

And he’s not stopping there. As ProPublica and the Lever reported last week, Leo is now using a $1.6 billion windfall he brought in last year from conservative financier Barre Seid — in one of the largest ever single contributions to a political nonprofit — to fund challenges to election and anti-discrimination laws, including in the high-profile Moore v. Harper case that could put the Supreme Court’s imprimatur on the fringe theory Trump embraced in his efforts to overturn his 2020 election loss to Joe Biden. 

That case in particular has renewed attention on the influence of dark money on the Supreme Court, as groups associated with Leo, former Trump lawyer John Eastman, and others funnel tens of millions of dollars into Moore. Democratic Senator Sheldon Whitehouse told the Guardian last week that he has been “pushing the Supreme Court to update their reporting requirements,” but it has “shown no interest.” “Rarely has such a noxious assemblage of amici appeared before this court,” Whitehouse wrote in an amicus brief with Representative Hank Johnson. “And their secrecy about their funders and connections does this court a grave disservice.”