The controversial author Michael Wolff finds himself at the centre of a fresh ethical storm following the release of email exchanges with convicted sex offender Jeffrey Epstein, revealing the writer provided strategic PR advice to the disgraced financier about Donald Trump.
The Incriminating Email Exchange
Among documents released by congressional Democrats from Epstein's estate this week, a December 2015 email thread titled "Heads up" shows Wolff warning Epstein that Donald Trump would likely face questions about their relationship during a Republican presidential primary debate. Epstein, who had already pleaded guilty in Florida to soliciting prostitution with a minor, responded by asking Wolff for personal advice on crafting a response for Trump.
Wolff's reply demonstrated a clear departure from standard journalistic practice: "I think you should let him hang himself. 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."
Pattern of Ethical Boundary-Pushing
This revelation fits a longstanding pattern for Wolff, who has built his career on blurring lines between journalism and the powerful subjects he covers. Back in 2003, during a failed $50 million bid to buy New York Magazine that Wolff helped orchestrate, he told media columnist David Carr that he hoped the sale would provide "incredible, undreamed-of access to the kinds of circles that it should be a part of."
The newly disclosed emails have sparked outrage among media professionals. Independent journalist Isaac Saul questioned whether Wolff's actions constituted journalism at all, while podcast host Brian Reed expressed astonishment at seeing Wolff "giving PR strategy to Jeffrey Epstein."
Wolff's Defence and History of Controversy
When approached for comment by The Guardian, Wolff did not respond. He later told CNN that he couldn't remember the context of the emails but suggested they were part of "an in-depth conversation with Epstein about his relationship with Trump."
This sparse explanation does little to address concerns about Wolff's journalistic methods, which have frequently drawn criticism for their casual approach to fact-checking. New York Times political reporter Maggie Haberman has argued that Wolff prioritises "larger truths and narratives" over factual accuracy, while Ben Smith, editor-in-chief of Semafor, notes that Wolff "considers himself a writer, not a journalist" and has never adhered to conventional journalistic rules.
Longstanding Epstein Connection
Wolff's relationship with Epstein dates back to the late 1990s, when the author was flown on Epstein's private jet to attend a conference. Even then, Wolff noted something unusual - Epstein was accompanied by three teenage girls. Wolff later described his initial reaction: "You didn't know what to make of this... Who is this man with this very large airplane and these very tall girls?"
Their connection continued over the years, with Wolff offering Epstein PR advice as early as 2007 when the financier faced his first criminal investigation. In a New York Magazine interview that year, Wolff recalled telling Epstein to change his language from "I like young girls" to "I like young women."
By 2017, their relationship had evolved into a more formal journalistic arrangement, with Epstein reportedly wanting Wolff to write his biography while Wolff sought information about Epstein's friendship with Trump for his book Fire and Fury. The two men conducted over 100 hours of recorded discussions at Epstein's Manhattan townhouse.
Wolff later described the setting of these interviews, noting "there were always a background of girls at Epstein's house" - a detail that raises questions about why the author showed such limited journalistic curiosity about the activities of a convicted sex offender.
Legal Battles and Continuing Controversy
Wolff's current legal battles extend beyond the Epstein revelations. Last month, Melania Trump threatened to sue him for over $1 billion for comments he made on his podcast suggesting her involvement in White House handling of the Epstein scandal. Wolff has responded by countersuing the former first lady, claiming she's attempting to shut down his reporting.
The author has raised more than $700,000 through a GoFundMe campaign he says will support legal costs and help "see behind the dark curtain of the Epstein affair."
These latest developments underscore the ongoing ethical questions surrounding Wolff's unique brand of access journalism. His ability to maintain relationships with powerful figures while writing explosive exposés about them continues to generate both bestselling books and serious concerns about where journalism ends and complicity begins.
