CNN  — 

The Supreme Court did not disclose its longstanding financial ties with former Homeland Security Secretary Michael Chertoff even as it touted him as an expert who independently validated its investigation into who leaked the draft opinion overturning Roe v. Wade.

The court’s inquiry, released last week with Chertoff’s endorsement, failed to identify who was responsible for the unprecedented leak. The decision to keep the relationship with Chertoff quiet is a reflection of a pattern of opacity at the nation’s highest court, whose rulings affect every American.

Former Homeland Security Secretary Michael Chertoff and Chief Justice John Roberts

CNN has learned from sources familiar with the arrangements that the court in recent years has privately contracted with The Chertoff Group for security assessments, some broadly covering justices’ safety and some specifically related to Covid-19 protocols at the court itself.

The estimated payments to Chertoff’s risk assessment firm, for consultations that extended over several months and involved a review of the justices’ homes, reached at least $1 million. The exact amount of money paid could not be determined. Supreme Court contracts are not covered by federal public disclosure rules and elude tracking on public databases.

The justices have long cloaked themselves in secrecy to the point of declining to respond to questions about potential conflicts of interest, or to reveal information about some court rules and ethics codes; or to release timely information about the justices’ health and public appearances.

The court’s decision to keep secret the prior arrangements with Chertoff, whose professional path has intersected over the years with Chief Justice John Roberts and other court conservatives, as it used him for a seal of approval, adds to controversy over the leak investigation itself.

“It’s at least a valid question why they went to someone who had a relationship with the court. Can we be sure he is objective? That’s part of the reason for disclosures,” Sean Moulton, a senior policy analyst at the Project on Government Oversight, told CNN.

Asked about specific Chertoff contracts and money estimates, the Supreme Court’s public information officer said only that “the Court as a matter of policy does not discuss security measures.” Court officials previously declined to respond to CNN’s questions about money paid to Chertoff.

A Chertoff Group spokeswoman declined to address questions about the firm’s previous financial dealings with the court and why Chertoff did not reveal the prior relationship. She referred questions to the Supreme Court.

Moulton said the routine government disclosure of contracts offer people a way to decide whether money is being reasonably spent, how one consulting contract price tag might compare with another and whether bids were sought or whether that process was skipped because the work was needed on an urgent basis.

“I think it’s a mistake to treat the judicial branch differently when it comes to these disclosures,” Moulton told CNN. “They are stewards of public funds and owe some accountability for how they use these funds.”

The report on the leak investigation, which was carried out by Supreme Court Marshal Gail Curley, did not identify how the draft opinion in Dobbs v. Jackson Women’s Health Organization was leaked, yet revealed a multitude of internal security shortcomings in protocols for confidentiality and computer use.

In a one-page public statement issued with the report, Chertoff wrote that Roberts had asked him “to independently review and assess the thoroughness of the investigation into the Dobbs draft opinion leak and to identify any additional useful investigative measures as well as actions that would improve the handling of sensitive documents in the future.”

The Supreme Court’s own statement on the matter emphasized that Chertoff had concluded that Curley “undertook a thorough investigation” and that Chertoff had declared that “at this time, I cannot identify any additional useful investigative measures.”

Personal connections in conservative circles

Chertoff, whose financial ties to the court have not been previously reported, already had well-known personal connections to the justices through his Ivy League education, prior judicial clerkships and tenure in the two Bush administrations.

A year ahead of Roberts at Harvard Law School, Chertoff and Roberts served in successive years as law clerks on the New York-based 2nd US Circuit Court of Appeals and then at the Supreme Court. (Roberts clerked for then-Associate Justice William Rehnquist, a conservative; Chertoff, for Associate Justice William Brennan, a liberal.)

In the early 1990s, as Roberts worked in the first Bush administration’s Department of Justice, Chertoff was tapped by President George H.W. Bush to be the US attorney in New Jersey. That post was previously held by another current justice, Samuel Alito.

Chertoff later took a turn through private practice and in 2003 joined Alito on the 3rd US Circuit Court of Appeals. Chertoff was appointed by President George W. Bush, in whose administration current justices Brett Kavanaugh and Neil Gorsuch also served. In 2005, Chertoff left the bench as Bush appointed him to be secretary of Homeland Security.

Previous work for the court

Chertoff set up his private firm in 2009, and court sources said he was hired to revamp court police security for the justices about four years ago.

During this period, CNN learned at the time, the court was trying a new approach in which each of the nine justices would have a permanent security detail of the same officers. (This was before their protection was enhanced as a result of the abortion case leak and regular protests at the court and at justices’ homes.)

Chertoff’s firm was then asked to advise the court in its response to Covid-19 and the justices’ safe return to courtroom proceedings.

Neither the court nor Chertoff responded to CNN’s questions regarding whether The Chertoff Group would have any part in carrying out his new recommendations, which accompanied the January 19 report, to improve the justices’ security in the wake of the leak.

The court has referred in its appropriations request to Congress to a past review by unnamed “security experts.” In public materials submitted to Congress requesting an additional $23 million this year for the care of its building and grounds, it sought $4.2 million for physical security upgrades “pursuant to a comprehensive review and recommendations by security experts.” No specific experts or consulting contracts were named. The court asked separately for another $2.8 million for “additional security upgrades” related to police kiosks and other security-related physical infrastructure. (The court’s total requested budget authority for 2023 is about $140 million.)

The safety of the justices has become a growing court concern, because of increasing protests at the justices’ homes and especially after attempted murder charges against a California man arrested last June near Kavanaugh’s Maryland home.

The January 19 report on the leak investigation was noticeably silent regarding scrutiny of the nine justices themselves, who divided acrimoniously in a 5-4 vote on whether to reverse the 1973 landmark ruling that first gave women nationwide a right to end a pregnancy. (The final opinion overturning Roe v. Wade came out on June 24.)

Last week’s report detailed the many law clerks and permanent employees who had been interviewed, and required to sign affidavits, to try to determine responsibility for the leak. But court officials initially said nothing about whether the justices were interviewed. On January 20, Curley revealed that she had spoken to each of the nine justices but had not asked them to sign affidavits.

Chertoff in his review of Curley’s report commented on the investigators’ own willingness to be candid and cooperative.

“Throughout my review,” he wrote, “the investigators were transparent, cooperative, and available to answer my questions about the process. At this time, I cannot identify any additional useful investigative measures.”