United States v. Alter, 1:23-cv-04781

The United States sued Miriam Alter to collect over $9 million in unpaid taxes, claiming she failed to pay taxes on funds received from religious organizations controlled by her family.
Rachel and Yaakov Biderman, Alter's sister and brother-in-law, were served deposition subpoenas including document requests related to the purchase and ownership of a Brooklyn property (the "Alter House").
The Bidermans asserted their Fifth Amendment privilege against producing any documents; the government moved to compel production.
Fact discovery closed, but the court partially reopened discovery solely to allow the government to seek the documents from the Bidermans.
When the Bidermans produced only a few signature exemplars and asserted the Fifth Amendment as to other documents, the government sought contempt sanctions; the court considered ex parte submissions from the Bidermans relating to their privilege claim.

Issue	Plaintiff's Argument	Defendant's Argument	Held
Whether the Bidermans can assert Fifth Amendment privilege against document production	The Bidermans have no real risk of prosecution and already waived the privilege.	Production could incriminate them and privilege was not waived.	Privilege applies; Bidermans need not produce more documents.
Whether the Bidermans waived their Fifth Amendment privilege by prior conduct	Late or inconsistent assertion of privilege equals waiver.	No waiver since they believed no further production was required and privilege cannot be lightly inferred.	No waiver; all presumptions against waiver were honored.
Applicability of the “act of production” doctrine	Requesting only existing, non-testimonial documents; privilege does not apply.	Production would implicitly admit existence, possession, and authenticity of possibly incriminating documents.	Act of production here would be incriminating; privilege applies.
Whether the "foregone conclusion" doctrine overrides the Fifth Amendment claim	Existence, control, and authenticity of documents is a foregone conclusion.	Government cannot demonstrate knowledge of existence/control/authenticity for the relevant period.	Government did not meet burden; doctrine not applicable.

Hoffman v. United States, 341 U.S. 479 (1951) (witness can assert Fifth Amendment if testimony might furnish a link in a chain of evidence for prosecution)
Estate of Fisher v. Comm’r of Internal Revenue, 905 F.2d 645 (2d Cir. 1990) (Fifth Amendment applies in civil proceedings, requires reasonable fear of prosecution)
United States v. Hubbell, 530 U.S. 27 (2000) (act of production privilege may apply if production communicates incriminating facts)
In re DG Acquisition Corp., 151 F.3d 75 (2d Cir. 1998) (waiver of Fifth Amendment privilege is not lightly inferred and must be clear)
United States v. Fridman, 974 F.3d 163 (2d Cir. 2020) (foregone conclusion doctrine requires proof of existence, control, and authenticity of documents at the relevant time)