Jack Smith

Donald Trump could have walked away unscathed from his squabble with the Department of Justice over sensitive documents he was hoarding at his Mar-a-Lago resort up until the moment investigators received recordings of him boasting about the documents and then sharing them with aides, a report revealed Friday.

According to the Wall Street Journal, officials at the risk-averse DOJ were willing to not pursue charges if the former president had handed the documents over after months of stalling, but the bombshell recordings forced their hand and resulted in special counsel Jack Smith seeking a 37-count indictment.

The Journal's Aruna Viswanatha and Sadie Gurman reported that the DOJ was reluctant to proceed with indicting a former president and there was a hope that an "off-ramp" would spare Attorney General Merrick Garland from pursuing criminal charges.

As they wrote, "Some officials at the time, even with evidence Trump might have obstructed the response to the May 11, 2022, subpoena demanding the production of classified documents, said their main interest in conducting the Mar-a-Lago search was to return any such material to the government’s possession."

The report continued, "Momentum shifted around February of this year, when investigators got hold of an audio recording of a July 21, 2021, meeting at Trump’s golf club in Bedminster, N.J., where Trump and his aides met with people working on an autobiography of his former chief of staff, Mark Meadows."

The report notes that those recordings were the smoking gun that took a simple settlement off the table, explaining, "At the time of the search and in the ensuing months, investigators had only heard rumors of Trump’s sharing sensitive documents with donors or other political allies, including on his plane, some of the people familiar with the matter said. They hadn’t established whether such claims were credible."

Adding that "authorities appeared at times to give Trump’s team the benefit of the doubt," the Journal report notes, "In bringing the case, Smith appears to be continuing to take a careful approach, charging dozens of counts but deferring to Trump’s legal team in other ways that are unusual, compared with how the Justice Department treats most federal criminal defendants facing similar charges."

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As Donald Trump and his lawyers head to court once again to face a second defamation lawsuit filed by E. Jean Carroll, he faces the very real prospect of a jury awarding her up to $100 million in punitive damages should a jury find in her favor.

According to a report from New York Times' Benjamin Weiser, Carroll's attorney is looking for a win and financial penalties at the outermost edge that will get the former president to cease smearing her client and that may come in the form of a massive punitive damage award.

The former president is already on the hook for $5 million from Carroll's previous lawsuit and her attorney is reportedly looking for a bigger payday after the former president launched another attack during his CNN town hall immediately afterward.

According to the Times' report, "Ms. Carroll’s complaint will be heard as part of a trial scheduled for January, stemming from verbal assaults he made against her in 2019. Ms. Carroll has said she lost her job as an advice columnist for Elle magazine after those attacks and is seeking at least $10 million in compensatory damages for harm to her reputation. After Mr. Trump’s recent CNN diatribe, she said she also wanted 'a very substantial punitive damages award' that would 'deter him from engaging in further defamation.'"

READ MORE: 'Display of strength': ex-federal prosecutor says Jack Smith is showing Trump how good his case is

“What I do know is that Donald Trump cares a lot about money,” attorney Roberta Kaplan explained. “And here, the prospect that he could have to pay millions of dollars in punitive damages each time he defames E. Jean Carroll again has to weigh on his mind.”

The threat of those punitive damages could be the tipping point that finally keeps Trump uncharacteristically quiet.

The Times is reporting that "Benjamin Zipursky, a Fordham Law School professor, said U.S. Supreme Court precedent has suggested that punitive damages should not exceed 10 times the compensatory damages. Using that as a guide, if Ms. Carroll obtained the $10 million in compensatory damages she seeks, a $100 million punitive damages award might be upheld.

Should Carroll prevail and win a massive punitive award, the former president may face the prospect of further humiliation, with the Times reporting that "Mr. Trump has a reputation for stiffing people who work for him, from laborers to lawyers. But plaintiffs who win money have leverage like liens on real estate and mandatory financial disclosures."

You can read more here.