Trump-obsessed writer Michael Wolff encouraged Jeffrey Epstein to blackmail then-presidential candidate Donald, emails reveal | 13 Nov 2025 | Discredited author Michael Wolff once encouraged Jeffrey Epstein to blackmail then-presidential candidate Donald Trump — insisting the convicted pedophile could generate a “debt” from him. The Trump-obsessed writer’s email exchanges with Epstein were among the trove of documents released by the House Oversight Committee on Wednesday. In one email, Wolff floated the possibility of intimidating Trump for his own benefit — as he warned Epstein that the then-GOP candidate could be asked about their alleged ties while on the campaign trail. “I hear CNN planning to ask Trump tonight about his relationship with you — either on air or in scrum afterwards,” Wolff wrote to Epstein in December 2015.  “I think you should let him hang himself,” he added in a follow-up the next day.