When someone offers you $100 million out of the blue to endorse them, that should trigger red flag alerts, especially for someone like Swift who zealously protects her image. It's likely that someone on her legal team pointed out the securities issue to her during a briefing, and she brought it up during negotiations with FTX (Rolling Stone notes that multiple members of the FTX C-Suite personally attempted to recruit her, and lawyers don't generally get involved in contract negotiations until an agreement in principle has been worked out.)