The National Enquirer’s alleged attempt to blackmail Amazon CEO Jeff Bezos with intimate photos could get the tabloid’s parent company and top editors in deep legal trouble and reopen them to prosecution for paying hush money to a Playboy model who claimed she had an affair with Donald Trump. Federal prosecutors are looking at whether the Enquirer’s feud with Mr Bezos violated a cooperation and non-prosecution agreement that recently spared the gossip sheet from charges in the hush-money case, two people familiar with the matter told The Associated Press on Friday. The clash between the world’s richest man and American’s most aggressive supermarket tabloid spilled into public view late Thursday when Mr Bezos accused it of threatening to print photos of him and the woman with whom he was having an extramarital affair. He said the Enquirer made two demands: stop investigating how the publication recently obtained private messages that Mr Bezos and his girlfriend had exchanged. And publicly declare that the Enquirer’s coverage of Mr Bezos was not politically motivated. Enquirer owner American Media Inc said Friday that its board of directors ordered a prompt and thorough investigation and will take “whatever appropriate action is necessary.” Earlier in the day, the company said it “acted lawfully” while reporting the story and engaged in “good-faith negotiations” with Mr Bezos. In recent months, the Trump-friendly tabloid acknowledged secretly assisting his White House campaign by paying $150,000 to Playboy centrefold Karen McDougal for the rights to her story about an alleged affair with Mr Trump. The company then buried the story until after the 2016 election. Mr Trump’s long-time personal attorney and fixer Michael Cohen pleaded guilty last year to charges that included helping to broker that transaction. Federal prosecutors considered the payment an illegal corporate contribution to Mr Trump’s campaign. In September, though, AMI reached an agreement with federal authorities that spared it from prosecution. It promised in the agreement not to break any laws. The deal also required the continuing cooperation of top AMI executives, including CEO David Pecker and Enquirer editor Dylan Howard. Now, federal prosecutors in New York are looking at whether AMI violated those terms, the people familiar with the matter said. A violation of the agreement could lead to criminal charges over the McDougal payments. And the resulting court proceedings could lay bare details of the gossip sheet’s cosy relationship with the president. The Enquirer and top executives could also be subject to state and federal extortion and coercion charges and prosecution under New York City’s revenge porn law, passed last year, which bans even the threat of sharing intimate photographs, legal experts said. Mr Bezos detailed his blackmail allegations in an extraordinary blog post. The intimate photos at issue include a ‘below the belt selfie’ of Mr Bezos and several revealing photos of Ms Sanchez, according to emails he released of his exchanges with AMI. “Of course I don’t want personal photos published, but I also won’t participate in their well-known practice of blackmail, political favors, political attacks, and corruption,” Mr Bezos said in explaining his decision to go public. “I prefer to stand up, roll this log over, and see what crawls out.”