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By Glenn Kirschner, former assistant U.S. attorney for the District of Columbia and NBC/MSNBC legal analyst

Jeff Bezos is the richest man in the world. He is also not a man who takes kindly to alleged blackmail attempts. On Thursday, he published a series of emails on Medium that appear to show American Media Inc. (AMI), the parent organization of the National Inquirer tabloid, threatening to publish compromising photos of the CEO of Amazon and owner of the Washington Post unless Bezos dropped an investigation into the tabloid’s coverage of his personal life.

AMI leveled this threat while it was a party to a cooperation agreement with federal prosecutors that required AMI to keep its nose clean and “commit no crimes whatsoever” for three years. All of this has prompted much discussion about whether AMI’s interactions with Bezos qualify as criminal extortion. The answer to the legal question is likely yes.

AMI leveled this threat while it was a party to a cooperation agreement with federal prosecutors that required AMI to “commit no crimes whatsoever.”

Yet again, fact appears stranger than fiction in America. To summarize: In January of 2019, the National Enquirer began publishing stories detailing Bezos’ alleged extramarital affair with Lauren Sanchez, a former TV anchor. The National Enquirer included in its stories private texts between Bezos and Sanchez, prompting Bezos to launch an investigation into how AMI acquired his private correspondence, and whether the National Enquirer’s stories were politically motivated.

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It appears that upon discovering this investigation, AMI told Bezos — in writing — that it would publish compromising, sexually explicit photos of Bezos and Sanchez unless Bezos and the Washington Post stopped investigating the Enquirer’s methods and issue a statement saying that Enquirer coverage of Bezos has not been politically motivated, a statement Bezos maintains is false.

This sordid and unusual tale is a voyeur’s dream. But it has taken on a new level of public interest due to the fact that AMI, through its CEO David Pecker, is cooperating with federal prosecutors as part of an ongoing investigation into campaign finance violations involving Donald Trump’s 2016 presidential campaign.

Indeed, AMI and David Pecker garnered much attention recently when federal prosecutors in the Southern District of New York announced a deal involving information about an alleged campaign finance violation committed in conjunction with Trump fixer Michael Cohen. The prosecutors agreed not to bring charges against AMI in exchange for AMI’s full and truthful cooperation. In that non-prosecution agreement, AMI admitted it paid for and buried a story — a practice called “catch-and-kill” — about an alleged affair between Trump and former Playboy Playmate Karen McDougal in an effort to keep the information from hurting Trump’s election chances. The federal agreement also stipulated that AMI would not be prosecuted provided the organization committed no new crimes in the three years following the date of the agreement, which was signed on September 20, 2018.

The question now becomes, did AMI commit a new crime by virtue of the Bezos blackmail scheme. (For its part, AMI has said it does not believe it did anything wrong but is looking into the matter.On Sunday, Elkan Abramowitz, an attorney for AMI CEO David Pecker, told ABC neither extortion nor blackmail was committed.) The stakes are quite high for AMI, as it has already confessed in detail to committing the campaign violation felony. So in the event that AMI is found to have violated the non-pros (non-prosecution) agreement, its earlier confession can be admitted as evidence if the prosecutors chose to charge AMI with extortion. In short, this feels like a case the prosecution can’t lose.

The stakes are quite high for AMI, as it has already confessed in detail to committing the campaign violation felony.

The crime of extortion involves threatening to harm a person in order to obtain something of value. In mob parlance, if someone says, “gimme a thousand dollars or I break your thumb,” that constitutes extortion. To be clear, there are more detailed legal requirements, particularly in the federal extortion statutes. However, it’s important to note that in this case, AMI doesn’t need to violate federal laws to break its agreement with SDNY prosecutors — violating New York State’s laws and criminal statutes would be enough.

The first element of extortion, threatening to harm another, seems more easily satisfied in this case than the second. Harm need not be of the physical, thumb-breaking sort. Harm to one’s reputation and standing in the community can suffice. It therefore seems clear that AMI threatened to “harm” Jeff Bezos’ reputation by publishing compromising, embarrassing and indiscrete material. A more nuanced question is whether AMI was attempting to secure “a thing of value.” AMI clearly was leveling the threat in an attempt to persuade Bezos to stop investigating how AMI came into possession of Bezos’ private messages. AMI also sought to have Bezos issue a statement — one that Bezos maintains is false — that the National Inquirer’s original articles about Bezos’ affair were not politically motivated.

AMI is obviously concerned about this information, otherwise it seems unlikely it would take the kind of risk it did. Accordingly, one can reasonably conclude that the there is real value, at least as far as AMI is concerned, in keeping Bezos, the Washington Post and by extension the general public from learning about how AMI acquired Bezos’ materials. Additionally, it’s apparently valuable to AMI that Bezos attempts to clear the company's name publicly. Although it may be impossible to quantify the value of these matters, they clearly qualify as things of value. Hence, prosecutors appear to have enough evidence to work with if they chose to charge AMI with extortion.

It should be noted that acts of extortion can also serve as the basis of a civil suit. In other words, Bezos could attempt to sue AMI for monetary damages. However, Let’s go out on a limb here and concluded that Bezos probably doesn’t need the money. The real issue is whether the facts as we know them thus far will inspire the SDNY prosecutors to charge AMI with a new crime.

Bezos could attempt to sue AMI for monetary damages. However, Let’s go out on a limb here and concluded that Bezos probably doesn’t need the money.

It may be that federal prosecutors use AMI’s potentially extortionist conduct in a different way. If AMI was charged with extortion, prosecutors ultimately would have to prove its case to a jury beyond a reasonable doubt. However, SDNY prosecutors might instead argue to the court that AMI breached the non-pros agreement and should therefore be prosecuted for the underlying campaign finance felony. This approach would have the fringe benefit of enjoying a much lower burden of proof, given that the question of whether someone violates a cooperation agreement is decided by a judge (not a jury) and generally requires a lower evidentiary standard (i.e., a preponderance of the evidence). Given that SDNY prosecutors probably have all the information they need from AMI and Pecker on the campaign violation front, this approach might prove an easier prosecutorial lift for them.

But perhaps the bigger question is what exactly is AMI trying to keep secret? It’s possible that AMI engages in this kind of immoral and quite probably illegal behavior more often than we know, as a series of new allegations following the Bezos blog post suggest. But even if this is the case, targeting someone with the resources of Bezos, particularly while contractually obligated to the government to commit no new crimes, seems supremely reckless.

There has been some speculation that a foreign government may have obtained Bezos’ information and provided it to AMI in an effort to retaliate against the Washington Post for reporting certain stories. Indeed, Bezos himself wrote that “Mr. Pecker and his company have also been investigated for various actions they’ve taken on behalf of the Saudi government.” Because the Post has been relentlessly reporting on the suspected involvement of the Saudi government in the murder of Washington Post columnist Jamal Khashoggi, perhaps the Saudis are working with AMI to embarrass Bezos as a form of payback. (Saudi Arabia's foreign minister has denied any involvement.) Although this theory enjoys a certain international intrigue, there are not nearly enough facts publicly available yet to make any sort of definitive conclusions.

Writing for NBC News, legal analyst Danny Cevallos notes that it will be difficult for AMI to claim this is merely a matter of journalistic inquiry or free speech. AMI is playing with fire, and this time it may well have been burned.