In jurisdictions across America, sophisticated entities facing possible investigation follow a well-established protocol: engage experienced counsel, conduct a comprehensive privileged risk assessment, and use that protected analysis to guide defensive strategy. Washington insider firms bill millions for this work. Corporate executives depend on it. Politicians rely on it. The approach, refined over decades by attorneys, has long served as the cornerstone of modern legal defense.

A July 2025 decision in the Eastern District of New York (EDNY) may have dismantled that defensive architecture entirely.

The Hidden Architecture of Executive Defense

Most clients never hear of a “privileged risk assessment” until they need one. When a Senator faces an ethics probe, when a tech company anticipates DOJ scrutiny, when a corporate executive prepares for congressional testimony—the first step is always the same: create a comprehensive, attorney-supervised vulnerability catalog. Fortune 500 companies often pay seven figures for these assessments. Political figures mortgage homes to afford them.

These assessments are brutally candid. They identify every weakness—the questionable trades, compromising emails, messy business dealings, even private relationships that could invite blackmail or optics issues. They determine what’s defensible, what demands preemptive disclosure, and what requires settlement. They map witnesses, predict pressure points, and game out potential prosecution scenarios.

The privilege surrounding these documents allows candor without fear of discovery. Executives can be honest because attorney-client protection prevents the assessment from becoming evidence against them. The entire defensive strategy depends on that protection.

The OneTaste Case Study

In 2017, OneTaste, Inc.—a San Francisco-based wellness company facing media scrutiny— retained a top D.C. law firm to conduct a privileged risk assessment in anticipation of potential litigation. The law firm instructed the client to prepare a privileged and confidential document and “…to gather information about any potential derogatory allegations that could be made against appellant, regardless of their credibility or veracity.”¹ The resulting document was marked “ATTORNEY-CLIENT PRIVILEGE: CONFIDENTIAL AND PRIVILEGED” on every page.

After his termination, a former IT contractor for OneTaste is alleged to have unlawfully accessed company servers and obtained the privileged risk assessment. He later provided it to federal investigators. According to defense filings, FBI personnel recognized that the materials were plainly privileged yet failed to follow Department of Justice filter protocols. Instead, the documents were allegedly used as an investigative roadmap: witnesses named in the assessment were interviewed, and theories flagged by company counsel as “potential vulnerabilities” became the foundation of the prosecution.

Years later, those same documents surfaced in the criminal case United States v. Cherwitz et al.,² leading to the conviction of former OneTaste executives Nicole Daedone and Rachel Cherwitz.

The Two-Stage Precedent: Conviction Then Nullification

When the defendants learned the government had obtained and used privileged materials, they moved to suppress them. The court ruled that individual defendants lacked standing to challenge government use of corporate privileged documents—even though the assessment had been created to protect those very individuals.

The trial proceeded; both defendants were convicted in June 2025.

Meanwhile, OneTaste had initiated a parallel civil proceeding under Rule 41(g) of the Federal Rules of Criminal Procedure, which allows parties to seek the return of property, including attorney-client privileged material. This matter–In re Petition Of One Taste, Inc.³–was assigned to the same judge as the criminal proceeding, who in turn assigned it to a magistrate judge for determination. The magistrate judge found, after an evidentiary hearing in April 2025, that the materials were indeed attorney-client privileged and ordered the government to return and destroy all copies. But in July 2025, the trial judge reversed that order—without taking testimony—declaring that no privilege had been established for any of the documents.

The result: stolen privileged materials had already been used to help secure convictions; post-trial the criminal court determined no privilege existed, nullifying the remedy for a tainted prosecution.

Why Practitioners Should Be Concerned

This new EDNY precedent upends the framework that has long protected attorneys and their clients.

• Corporate Executives: Every company facing investigation prepares privileged assessments under counsel’s supervision. If a disgruntled insider can steal those documents and deliver them to investigators—with courts later ruling “no privilege ever existed”—the defensive tool becomes a liability.
• Political Figures: Senators, Representatives, Cabinet, and campaign officials routinely commission privileged assessments before ethics or FEC inquiries. Under this precedent, a terminated staffer could hand that document to prosecutors, where it could be used as a roadmap with no judicial remedy.
• Law Firms: High-end firms bill hundreds of thousands per engagement for these analyses. If courts can re-label such materials as “not privileged,” the value—and safety—of this work collapses.
• General Counsel: Advising a client to conduct a privileged self-assessment could now expose that client to greater risk than doing nothing at all.

Weaponizing Privilege

Now that privilege can be contested and weaponized by the government, a playbook is beginning to emerge.

Once prosecutors target an organization, an insider is approached. That insider, who has access to privileged materials, delivers the solicited materials to law enforcement. Investigators can then use the ill-gotten gains as a roadmap.

The result is that the risk assessment process—long part of a robust legal defense—now becomes the prosecution’s weapon.

The Appeal Before the Second Circuit

OneTaste has appealed this July 2025 EDNY ruling to the U.S. Court of Appeals for the Second Circuit (Case No. 25-1721-cv).

Its brief argues that the district court committed procedural and substantive error:

• Procedural: The court reversed a magistrate’s factual findings without conducting an evidentiary hearing or allowing cross-examination of witnesses, in violation of established standards.
• Substantive: Uncontroverted sworn declarations from company personnel and outside counsel established that the documents were communications seeking legal advice, intended to be and kept confidential. The government offered no evidence to the contrary—only argument.

If the Second Circuit affirms, the ruling would establish that privilege is not a shield but a suggestion—valid only until the government objects.

If the EDNY decision stands, every privileged assessment becomes a potential prosecution tool.

What’s at Stake for the Legal Profession

Privileged risk assessments are not fringe practices—they are core to the business model of Washington and Wall Street law firms. They make candid self-scrutiny possible. Remove that protection, and the entire system of preventive legal strategy collapses.

Executives will stop being honest with counsel. General counsels will advise silence over transparency. Firms will lose one of their most valuable service lines. And prosecutors will gain an unfair advantage built on stolen materials.

The Choice Before the Second Circuit

The appellate panel now faces a stark question:

• Affirm the EDNY ruling and create precedent allowing stolen, clearly marked privileged documents to be deemed “not privileged” after the fact—encouraging theft, chilling candor, and dismantling the architecture of legal defense; or
• Reverse the ruling and restore attorney-client privilege as a foundational safeguard of effective counsel and due process.

Every practitioner who has ever drafted, reviewed, or relied on a privileged assessment should be watching this appeal.

The question before the Second Circuit is therefore not about OneTaste, but about whether attorney-client privilege remains inviolate or becomes retroactively voidable when convenient for the prosecution and the court.

Disclaimer:

The views and opinions expressed in this article are those of the author and not necessarily those of The National Law Review (NLR). The NLR does not answer legal questions, nor will we refer you to an attorney or other professional if you request such information from us. If you require legal or professional advice, kindly contact an attorney or other suitable professional advisor. Please see NLR’s terms of use.

1. Case no. 25-1721, Dkt. 48.1 at 13.

2. United States v. Cherwitz et al., No. 23-cr-146 (E.D.N.Y.).

3. In re Petition of OneTaste, Inc., No. 25-1721-cv (2d Cir.).