David Pecker, the CEO of American Media Inc. (AMI), has turned on his longtime friend President Donald Trump and was granted immunity from prosecution for information in the ongoing “hush money” investigation of Trump’s former lawyer, Micheal Cohen.

Prosecutors granted immunity to Pecker and AMI’s chief content officer, Dylan Howard, so they would describe Trump’s involvement in Cohen’s payments to porn star Stormy Daniels and Playboy Playmate Karen McDougal during the 2016 campaign, including Trump’s knowledge of the deals. Prosecutors also have indicated that Pecker and Howard won’t be criminally charged for their participation in the deals.

In addition, court papers connected to Cohen’s guilty plea on Tuesday say that Pecker offered to help Cohen and Trump during the campaign keeping negative stories about the president out of the media by paying for stories and then never publishing them — a practice known as “catch and kill.”

Trump and Pecker have been friends since the 1990s, and have remained so after Trump became president. The media mogul visited the White House last year. Pecker has used his media holdings to shield Trump when he was a New York real estate developer and reality television star and Pecker’s publications have defended Trump as a presidential candidate.

“Holy shit, I thought Pecker would be the last one to turn,” a Trump friend told the Vanity Fair.

But Pecker and Trump haven’t spoken in roughly eight months, according to a source at AMI. Howard remains particularly angry at Trump, two people close to Howard said. “There is no love lost,” one person familiar with Howard’s thinking said. Another person said Howard “hates Trump” and feels “used and abused by him,” Vanity Fair reported.

The White House and Trump have repeatedly said that he has done nothing wrong relating to the hush money. In an interview on Wednesday, Trump said that he knew about the two payments only “later on,” without specifying when. However, in a September 2016 tape recording released by Cohen’s attorney Lanny Davis, Trump can be heard discussing with Cohen whether to buy the rights to McDougal’s story from AMI.