Trump biographer: Epstein joked about his legal troubles while orchestrating defense

A bestselling author has detailed the indifference Jeffrey Epstein displayed toward the criminal charges pursued against him between 2006 and 2008.

In a new column for his Substack, HOWL, Michael Wolff described how "unconcerned" and "uncaring" the disgraced financier was about the investigation. The years-long investigation began after a report was filed with Palm Beach police regarding alleged abuse at his Florida residence.

Wolff alleged on Monday that he met with Epstein, who died in a Manhattan jail cell in 2019, on multiple occasions during that period. At each meeting, Wolff described Epstein's remarkably composed demeanor.

"He was matter-of-fact, blithe, incapable of not making a joke about his situation, and as well, resigned to people not understanding or refusing to accept the nature of his desires. ('I'd be in much better shape if this were a gay thing.')," Wolff wrote.

At the same time, Epstein was also a strategic strategist regarding his legal defense, according to Wolff.

"He coolly laid out the field of play: the various characters both in Palm Beach and in the Justice Department; the legal maneuvers on his part and against him; his dream-team lineup of lawyers; and a defense of his own position," the author alleged.

Wolff recalls Epstein showing little concern about the outcome of his legal battle or its impact on his reputation—until he was taken into custody.

"Epstein, who seemed to remain unconcerned, if not uncaring, about the accusations against him and the legal efforts to punish him, and entirely confident that all would be settled and dealt with, suddenly accepted his plea in 2008 and immediately entered prison in Palm Beach," Wolff wrote.

It would not be until 2010 that Conchita Sarnoff's investigation, published by the Daily Beast, revealed the plea agreement that allowed Epstein to avoid more serious charges and federal prosecution despite extensive evidence of criminal conduct. Much of Epstein's sentence was served through a work-release program.

Wolff, who is co-host with Joanna Coles of the Daily Beast's podcast Inside Trump's Head, has faced scrutiny over his correspondence with Epstein. In his latest Substack, Wolff explained his multiple meetings with Epstein as an effort to understand how the financier was managing the investigation.

"I had never known anyone to be the subject of a criminal investigation and was, I confess, a curious witness to how he would handle this disgrace and humiliation," Wolff said.

The journalist has previously stated his goal was to document his interactions with Epstein, covering only what he says he "personally saw or heard."

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