The Bulwark Podcast Ben Wittes and Anna Bower: Trump's Reparations Demand
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Oct 23, 2025 
Anna Bower, a Senior Editor at Lawfare and investigative reporter, shares her surprising communication with U.S. Attorney Lindsey Halligan, discussing the peculiar norms surrounding prosecutors reaching out to the media. Meanwhile, Ben Wittes, Editor-in-Chief of Lawfare, delves into the implications of Trump's outrageous demand for $230 million in damages from the DOJ, highlighting ethical conflicts for involved attorneys. The duo navigates through legal intricacies and absurdities surrounding high-profile prosecutions with sharp insight and wit.
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Unexpected Signal From A U.S. Attorney
- Anna Bower received unsolicited Signal messages claiming to be Lindsey Halligan while at home relaxing in pajamas.
- She verified Halligan by asking where they first met and confirming a shared memory from a past courthouse dinner at the Breakers.
Prosecutorial Norms Were Ignored
- Halligan's outreach was unusual because it involved commenting on another outlet's reporting about an ongoing prosecution.
- Prosecutors normally avoid discussing grand jury matters or informal public back-and-forths about pending cases.
Signal Use Raises Recordkeeping Red Flags
- Halligan used Signal with disappearing messages and later claimed the conversation was off the record.
- That behavior raises Federal Records Act and media-relations preservation concerns and shows unfamiliarity with off-the-record norms.