Michael Cohen, Donald Trump's former personal lawyer and fixer, once said he would take a "bullet" for the president.
But instead of shielding his former client, Mr Cohen painted a target on his back on Tuesday and pushed him into the firing line.
The brash New Yorker's bombshell admission in court that he paid hush money to two women before the 2016 election at the direction of Mr Trump appears to implicate Mr Trump himself in a crime.
On the same day, a jury in Virginia found former Trump campaign chairman Paul Manafort guilty of eight financial crimes unrelated to the campaign. While that conviction does not directly implicate Mr Trump, it will bolster prosecutors in the office of special counsel Robert Mueller, whose investigation Mr Trump has branded a witch hunt.
The cases have sparked debate about what the legal, and political, ramifications could be for the US president.
Can Trump be prosecuted?
Whether a president can be prosecuted, remains a matter of legal dispute.
US Justice Department guidelines say a sitting president cannot be charged, although the US Supreme Court has never ruled on the matter.
"This brings President Trump closer into the criminal conduct," Daniel Petalas, a former prosecutor in the Justice Department's public integrity section, told the Associated Press.
"The president has certain protections while a sitting president, but if it were true, and he was aware and tried to influence an election, that could be a federal felony offence. This strikes close to home."
Rudy Giuliani, Mr Trump's current personal lawyer, quickly tried to distance the president from the proceedings. He noted in a statement that "there is no allegation of any wrongdoing against the president in the government's charges against Mr Cohen."
And prosecutors notably did not go as far as Cohen did in open court in blaming the president, saying the lawyer acted "in coordination with a candidate or campaign for federal office for purposes of influencing the election".
While the Justice Department's Office of Legal Counsel has held that a president cannot be indicted while in office, there would presumably be no bar against charging a president after he leaves the White House.
What could be the political fallout?
If a criminal case is not pursued, then the likely consequences would be political.
With the Republicans currently in control of Congress, there is very little chance of impeachment proceedings being launched.
That could change in November, however, if the Democrats were to take back control of the House and Senate in the midterm elections.
"Obviously it's not good for Trump," Sol Wisenberg, who conducted grand jury questioning of President Bill Clinton during the Whitewater investigation, said of Cohen's plea bargain.
"I'm assuming he's not going to be indicted because he's a sitting president," Mr Wisenberg added. "But it leads him closer to ultimate impeachment proceedings, particularly if the Democrats take back the House."
That is the fear of Republicans.
“This just underscores the importance of the midterms and keeping the house,” a Republican close to the White House told Politico. “If Nancy Pelosi is speaker, Donald Trump will face impeachment.”
Ms Pelosi was quick to seize on the developments, saying Cohen's guilty plea places Mr Trump "in even greater legal jeopardy".
The top Democrat also said the Manafort conviction was "further proof that Special Counsel Mueller’s team and prosecutors in New York are conducting thorough and professional investigations".
Will Cohen's case impact the Mueller probe?
Cohen's case is being handled by prosecutors in New York, rather than the team of investigators in the Mueller probe, which is looking at Russian election meddling and possible collusion between Moscow and the Trump campaign.
And Mr Mueller, himself, decided months ago that claims of campaign finance violations involving payments to women before the presidential election fell outside of his purview.
However, the Cohen case could give Mueller a boost.
Laurie Levenson, a former federal prosecutor and professor at Loyola Law School in Los Angeles, argued that Cohen's plea knocks back the argument that the investigations swirling around Mr Trump are a "witch hunt".
"No longer can you say Mueller is on a witch hunt when you have his own lawyer pleading guilty to things that were designed to impact the election," she told the Associated Press.
Manafort ruling could fuel Mueller probe
But Cohen's admission is still not as important for Mr Mueller as the ruling in the Manafort trial.
Timothy Belevetz, a former federal prosecutor now with the firm Holland & Knight, described the conviction as “an important milestone” for Mr Mueller’s team.
“So far, the office has charged more than 30 individuals and has secured a number of guilty pleas, which is not insignificant,” he told the Washington Post. “This is a big win for the special counsel.”
Mr Trump earlier tried to downplay the significance of the court case.
“This has nothing to do with Russian collusion,” the US President told reporters on Tuesday as he travelled to a campaign rally in West Virginia. “This is a witch hunt, and it’s a disgrace.”
But that apparently wasn't the view of many inside the White House.
“There was political momentum building to wrap up the Mueller probe soon,” a former administration official told Politico.
“At the very least, in the short term, these two developments will pretty significantly bolster the office of the special counsel and people’s perceptions of it.”