Disgraced author Michael Wolff once provoked Jeffrey Epstein to blackmail the then-presidential candidate Donald Trump, claiming that doing so could give the convicted sex offender leverage or generate a "debt" Trump would owe him. Email exchanges between the Trump-obsessed writer and the pedophile were part of a cache of documents released by the House Oversight Committee on Wednesday.
In one of the messages, Wolff appeared to suggest using intimidation tactics against Trump for personal gain, warning Epstein that the then–Republican presidential candidate might face questions about their alleged connection during his campaign. "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.
Plot to Blackmail Trump

"I think you should let him hang himself," he added in a follow-up the next day. "If he says he hasn't been on the plane or to the house, then that gives you a valuable PR and political currency. You can hang him in a way that potentially generates a positive benefit for you, or, if it really looks like he could win, you could save him, generating a debt."
Wolff — best known for writing 'Fire and Fury,' his controversial "tell-all" about Trump's first term — went on to suggest that Trump might have even spoken favorably about Epstein at some point during his campaign.

"Of course, it is possible that, when asked, he'll say Jeffrey is a great guy and has gotten a raw deal and is a victim of political correctness, which is to be outlawed in a Trump regime," Wolff noted.
Wolff also speculated that Epstein could be the "bullet" capable of ending Trump's 2016 campaign if he chose to publicly reveal details of their past association — and even suggested that Epstein should prepare a plan for how to use that information.
"The more Trump looks real, or perish the thought, inevitable, the more reporters are going to focus on this, so, as you will not be surprised, you need a strategy," the author wrote in a January 2016 email exchange.
His Soft Tone
In February 2016, Epstein emailed Wolff to say that as Trump's popularity in the polls continued to soar, more and more reporters were reaching out to him for comment. "Yeah, you're the Trump bullet," Wolff replied.

"NYT called me about you and Trump. Also, Hillary campaign digging deeply. Again, you should consider preempting," Wolff wrote in another email later that month.
Just before the 2016 election, Wolff emailed Epstein again, this time with the subject line, "Now could be the time."
"There's an opportunity to come forward this week and talk about Trump in a way that could garner you great sympathy and help finish," Wolff wrote. "Interested?"

Wolff, who built much of his career around writing about Trump's presidency, found massive success with his first book, 'Fire and Fury', which sold nearly 2 million copies within its first three weeks of release in January 2018. He went on to publish three more books about Trump's time in office.
Shortly after Trump's election win, Wolff even bragged to Epstein that he was working on a Trump book "for a pile of cash."
"So... I'm doing this Trump book for a pile of money and with so far quite a bit of co-operation from them (DT called me the other day and spent 45 minutes on the phone ranting and raving about the media–alarming)," he wrote in February 2017.

Wolff later asked Epstein to connect him with two people who could provide "off-the-record insight" into how the White House operated.
Trump, meanwhile, blasted Wolff's 'Fire and Fury', dismissing it as "trash" and "full of lies." The book alleged that Trump was an "absentee father" to his five children and "a notorious womanizer" who had little interaction with his wife, Melania.
Although 'Fire and Fury' became a bestseller, Wolff's so-called insider account of Trump's White House was heavily criticized by many journalists for its questionable sourcing and lack of accuracy.