Last Friday, CNN reported that former Department of Homeland Security Secretary Michael Chertoff, whom the Supreme Court chose to audit its investigation of the leak of the draft opinion in Dobbs v. Jackson Women’s Health Organization, has earned at least $1 million in prior security-related contracts with the Court. This information appears nowhere in the report of the Supreme Court Marshal’s inquiry, which Chertoff blessed as “a thorough investigation within their legal authorities.”

Chertoff, who now leads a private risk management firm, has long assisted the Court with general security assessments, including the development of its COVID-19 protocols. But these tasks are fundamentally distinct from reviewing the results of a high-profile investigation that could, in theory, implicate the justices or people close to them. And although the Marshal’s office focused on Court employees, many of whom had their phone records and legal research search histories examined, it all but ignored the possibility that the justices themselves were involved. The Marshal explained this omission by asserting that “no credible leads…implicated the Justices or their spouses,” and that the office “did not believe it was necessary to ask the Justices to sign sworn affidavits.”

Chertoff described the Marshal’s investigators as “transparent, cooperative, and available to answer [his] questions about the process.” But his longstanding relationships with the Court raises the obvious question of whether he can objectively review a probe that he has a powerful financial incentive to declare sufficient. “At this time, I cannot identify any additional useful investigative procedures,” he wrote in a preface to the report, a statement that suggests he may or may not have actually read it.


As CNN’s Joan Biskupic reported, also absent from the report was any mention of Chertoff’s connections with the conservative justices, which date to his time in law school, when he overlapped with Chief Justice John Roberts at Harvard. Both men clerked on the Second Circuit Court of Appeals and on the Supreme Court, and later served in President George H.W. Bush’s administration. Chertoff and Justice Samuel Alito overlapped as judges on the Third Circuit Court of Appeals; Chertoff and Justices Neil Gorsuch and Brett Kavanaugh all worked in President George W. Bush’s administration.

Of course, none of this history was a secret in a world where Wikipedia exists. But in the context of recent reporting about Justice Samuel Alito’s alleged history of leaking high-profile Supreme Court cases, the links between Chertoff and the conservative justices creates doubt about his ability to “independently review and assess the thoroughness of the investigation,” as he described it. 

The Court insists on its right to police itself even though it is and has always done a terrible job of doing so. Despite Roberts’s vows to get to the bottom of the matter, the Marshal’s investigation was unable to identify the culprit. Now, we know that the most powerful people in the building were never seriously treated as suspects. Perhaps a truly independent auditor would have pointed out this glaring flaw. Instead, the Court hired a friendly face who—sure enough—looked the other way.

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