Now playing
03:03
Toobin: 'Appalling behavior' on AMI's part
John Oliver addressed the recent fatal police shootings of Daunte Wright and Adam Toledo in a passionate monologue on "Last Week Tonight."
Last Week Tonight/HBO
John Oliver addressed the recent fatal police shootings of Daunte Wright and Adam Toledo in a passionate monologue on "Last Week Tonight."
Now playing
01:38
John Oliver to White Americans: 'March in the streets'
CNN
Now playing
03:20
Brianna Keilar: Fox is not news no matter what it calls itself
John Avlon 0413 Wallace
CNN
John Avlon 0413 Wallace
Now playing
03:31
Avlon compares Tucker Carlson's comments to George Wallace
Fox News/Twitter
Now playing
01:33
ADL wants Fox News to fire Tucker Carlson over racist comments
Now playing
01:54
'You think I'm racist': Former Fox News host storms off camera
CNN
Now playing
03:37
'The fraud is this farce': Cuomo calls out Fox News host
CNN
Now playing
05:00
Watch Alisyn Camerota sign-off CNN's New Day
Camerota Berman both
CNN
Camerota Berman both
Now playing
02:33
CNN anchor Alisyn Camerota gets surprise tribute from co-anchor
CNN/HBO/"Q: Into the Storm"
Now playing
05:35
Filmmaker says he potentially uncovered man behind QAnon
BOSTON, MA - AUGUST 30:  Anti-vaccine activists hold up signs during a protest in front of the Massachusetts State House against Governor Charlie Baker's mandate that all Massachusetts school students enrolled in child care, pre-school, K-12, and post-secondary institutions must receive the flu vaccine this year on August 30, 2020 in Boston, Massachusetts.  (Photo by Scott Eisen/Getty Images)
Scott Eisen/Getty Images
BOSTON, MA - AUGUST 30: Anti-vaccine activists hold up signs during a protest in front of the Massachusetts State House against Governor Charlie Baker's mandate that all Massachusetts school students enrolled in child care, pre-school, K-12, and post-secondary institutions must receive the flu vaccine this year on August 30, 2020 in Boston, Massachusetts. (Photo by Scott Eisen/Getty Images)
Now playing
03:06
Research exec: Far-right groups pushing vaccine as 'mark of the beast'
stelter chauvin trial international coverage kethevane gorjestani sot rs vpx_00000000.png
stelter chauvin trial international coverage kethevane gorjestani sot rs vpx_00000000.png
Now playing
02:19
How the rest of the world is covering the Derek Chauvin trial
CBS This Morning
Now playing
01:57
Hunter Biden makes rare comment about seized laptop
Fox News
Now playing
03:43
Tucker Carlson's interview with Gaetz gets uncomfortable
NEW YORK, NY - FEBRUARY 09: News headlines on the impeachment trial of Donald Trump are displayed outside of the Fox headquarters on February 09, 2021 in New York City. After listening to nearly four hours of legal arguments, the Senate has voted on Tuesday to move ahead with the impeachment trial of former President Trump. (Photo by Spencer Platt/Getty Images)
Spencer Platt/Getty Images
NEW YORK, NY - FEBRUARY 09: News headlines on the impeachment trial of Donald Trump are displayed outside of the Fox headquarters on February 09, 2021 in New York City. After listening to nearly four hours of legal arguments, the Senate has voted on Tuesday to move ahead with the impeachment trial of former President Trump. (Photo by Spencer Platt/Getty Images)
Now playing
04:03
Dominion Voting Systems files $1.6 billion lawsuit against Fox News
 President Donald Trump waves as he departs on the South Lawn of the White House, on December 12, 2020 in Washington, DC.
Al Drago/Getty Images
President Donald Trump waves as he departs on the South Lawn of the White House, on December 12, 2020 in Washington, DC.
Now playing
01:35
Trump praises Capitol rioters 'hugging and kissing the police'

Editor’s Note: Elie Honig, a former federal and state prosecutor, is a CNN legal analyst and Rutgers University scholar. The views expressed in this commentary are his own. View more opinion articles on CNN.

(CNN) —  

On Thursday, Amazon founder Jeff Bezos posted a blog post on Medium claiming that American Media Inc., publisher of the National Enquirer, committed “extortion and blackmail.” Bezos alleged that the publisher threatened to release embarrassing pictures of him unless he ended his investigation of leaks to AMI. If true, this raises a difficult but important legal question: Do AMI’s actions constitute criminal extortion?

Elie Honig
Courtesy Lowenstein Sandler
Elie Honig

I’ve charged and tried federal extortion cases. Admittedly, I had it easy. My cases involved the mafia, which tended to make obvious, explicit threats that fell squarely within both the common-sense and legal definitions of the term “extortion.” In one case, my defendants threatened to cut off the victim’s fingers if he didn’t pay them cash by the end of the week. That’s Hollywood-obvious extortion.

Bezos’ allegations are a much closer call. Reasonable people can differ on this, but if, hypothetically, legal action were to be taken and I was back in the prosecutor’s chair, I’d still bring the charge. Here’s why.

Federal law defines the crime of extortion as (1) obtaining property from another (or attempting to do so), (2) by wrongful use of actual or threatened force, violence or fear. Let’s break that down.

On the first prong, If the allegations are true, AMI plainly tried to obtain something from Bezos: an end to the leak investigation. The question, however, is whether that something qualifies as “property.” If AMI had threatened to release the photographs unless Bezos paid it money, or gave it Amazon stock, then “property” would clearly be involved. The facts are murkier here. AMI likely would argue that it did not try to obtain any “property” – it merely tried to get Bezos to stop doing something.

My counter-argument as a prosecutor would be that AMI recognized that Bezos’ investigation might have led to the discovery of information that (1) would have had value to Bezos in his ongoing public relations battle and potential lawsuit against AMI, and (2) would have been damaging to AMI. The law defines “property” very broadly – it does not have to be monetary, or worth more than a nominal amount, or even tangible.

Here, I’d argue that Bezos’ investigation had real value to both parties. Exhibit A: Just look at the extreme and outrageous steps AMI took to try to stop it. You don’t threaten to publish sexually humiliating photographs of another person – never mind the world’s richest person – unless there’s something big at stake.

On the second prong, according to Bezos’ claim, AMI seemingly used fear. The question is whether it used that fear “wrongfully.” AMI would likely argue that it was engaged in ongoing negotiations with Bezos over releasing potential legal claims against one another. Sure, the negotiations were tough and even distasteful, AMI would probably claim, but welcome to the real world of big money and big business.

Indeed, there is a fine line between hard-edged business or legal negotiations and extortion, and prosecutors should hesitate to criminalize aggressive tactics. Here, however, AMI’s conduct goes beyond the pale: It allegedly sent Bezos an email detailing lurid and potentially humiliating photos of him before siccing its lawyers on Bezos to try to extract a “settlement.”

I’d be comfortable arguing to a jury that this goes well beyond legally acceptable boardroom hardball. AMI also might claim that it acted on the advice of its attorneys – a criminal defense known as “advice of counsel” – but I’d counter that nobody could reasonably believe it was truly lawful to negotiate by threatening to publish stolen nude photos of an adversary.

Get our free weekly newsletter

Again, we don’t yet know the facts and we can’t conclude guilt in this situation based on allegations made on a Medium post.

But if what Bezos alleges is indeed true, this is a close call, right on the razor’s edge. If I were arguing this as part of a case in court, here’s what I would say: In the end, juries tend to decide cases based largely on their gut instincts. AMI’s alleged conduct here was so over the top, so distasteful, that I’d be confident I could sway a jury that it crossed the line from aggressive business tactics and into criminal extortion.