WASHINGTON (AP) — President Donald Trump's longtime fixer, Michael Cohen, once said he'd take a bullet for his boss, but on Tuesday he pleaded guilty to eight felonies and described payoffs to women at Trump's direction before the 2016 election.

The development marked the pivot point in which Cohen went from ally for years to a potential threat to Trump. Under the agreement, Cohen, 51, could get four to five years in prison at his Dec. 12 sentencing. His account appears to implicate Trump in a crime, though whether — or when — a president can be prosecuted is in dispute.

Key moments in how it all went down:

2016

Trump is a Republican presidential candidate and eventually the party's nominee. At Trump's direction, Cohen says, he and Trump arrange to pay adult-film actress Stormy Daniels $130,000 and former Playboy model Karen McDougal $150,000 to influence the election — presumably to keep their allegations of sexual encounters private. In entering the plea Tuesday, Cohen did not specifically name the two women or even Trump, recounting instead that he worked with an "unnamed candidate." But the amounts and the dates all line up with the payments made to Daniels and McDougal.

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Nov. 4, 2016

The Wall Street Journal reports that the company that owns the National Enquirer agreed to pay $150,000 to McDougal for her story of an affair with Trump in 2006, the year after Trump married Melania Trump. In a statement, American Media Inc., which is supportive of Trump's campaign, says it didn't buy McDougal's story but rather two years' worth of columns. White House spokeswoman Hope Hicks denies there had been an affair.

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Nov. 8, 2016

Trump defeats Democrat Hillary Clinton in an upset.

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Jan. 12, 2018

The Wall Street Journal reports that Cohen arranged a $130,000 payment to Daniels a month before the election as part of an agreement that barred her from publicly discussing their alleged 2006 affair. Cohen says Trump "vehemently denies any such occurrence."

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Feb. 13, 2018

Cohen says that he personally paid Daniels and that he received no reimbursement from the Trump Organization or the campaign. Neither was "party to the transaction," he says. Cohen says later the money came from a home equity line to an account for a personal corporation.

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March 2018

McDougal files a lawsuit against American Media Inc., seeking to end a contract with the company. She tells CNN that the company bought her rights to tell her story under false circumstances and then killed the story to protect Trump. She also claims she had a lengthy affair with him in 2006. American Media says she's been free to tell her story since 2016. Through representatives, Trump denies the affair.

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April 5, 2018

Speaking to reporters aboard Air Force One, Trump denies knowing about the payment to Daniels. Asked why Cohen made the payment, Trump says, "You'll have to ask Michael Cohen."

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April 9, 2018

The FBI raids Cohen's office, seizing records on topics including a $130,000 payment to Daniels. Furious, Trump calls the raid a "disgrace" and says the FBI "broke into" his lawyer's office. He also tweets that "Attorney-client privilege is dead!" The raid is overseen by the U.S. attorney's office in Manhattan and is based in part on a referral from special counsel Robert Mueller, says Cohen's lawyer, Stephen Ryan. Cohen had said he took out a personal line of credit on his home to pay Daniels days before the 2016 election without Trump's knowledge.

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April 26, 2018

Trump acknowledges that Cohen represented him in the "crazy Stormy Daniels deal." He tells "Fox & Friends" that "there were no campaign funds going into this which would have been a problem."

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May 2, 2018

Trump attorney Rudy Giuliani tells "Hannity" that the payment to Daniels had been "funneled through a law firm, and the president repaid it." He later says that proves the payments didn't violate campaign finance laws. White House press secretary Sarah Huckabee Sanders says Trump "eventually learned" about the payments.

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May 4, 2018

Reporters remind Trump of his previous denial of the payments to Daniels. The president blasts the media for focusing on "crap" stories like the Daniels matter and claims that "virtually everything" reported about the payments had been wrong. Daniels' attorney, Michael Avenatti, tweets, "How stupid do they think all of us are?"

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July 20, 2018

People familiar with the investigation say Cohen secretly recorded Trump discussing a potential payment for McDougal two months before the election. Giuliani says that the payment was never made and that the brief recording shows Trump did nothing wrong. In it, Cohen is heard saying that he needed to start a company "for the transfer of all of that info regarding our friend David," a possible reference to David Pecker, Trump's friend and president of American Media Inc.

When Cohen begins to discuss financing, Trump interrupts him and asks, "What financing?"

"We'll have to pay," Cohen responds.

The audio is muffled, but Trump can be heard saying "pay with cash," though it isn't clear if he is suggesting to pay with cash or not to pay with cash. Cohen immediately says, "No, no, no" and Trump can then be heard saying, "check."

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Aug. 21, 2018

Cohen pleads guilty to campaign-finance violations and other charges, saying he and Trump arranged the payment of hush money to Daniels and McDougal to influence the election.