Cohen is not the only former Trump associate to be convicted of a crime - former Trump campaign manager Paul Manafort was found guilty of financial fraud-related crimes on Tuesday, former national security adviser Mike Flynn is awaiting sentencing, and former Trump campaign aide George Papadopoulos has pleaded guilty to lying to the Federal Bureau of Investigation.
Mr Trump lashed out at former longtime lawyer Michael Cohen, saying the campaign finance violations Mr Cohen pleaded guilty to in federal court in NY on Tuesday were "not a crime" - even though prosecutors and Mr Cohen agreed that they were.
The president has repeatedly voiced frustration that Attorney General Jeff Sessions has been unwilling to intervene into investigations into Trump and his allies, including the ongoing special counsel probe into possible collusion between his campaign and Russian Federation.
The guilty plea was a double blow the to President and happened at nearly the same time as former campaign chairman, Paul Manafort, was convicted of financial crimes. But veteran federal prosecutors say the eight convictions for financial crimes validate the special counsel established to investigate ties between Trump's campaign and Russian Federation.
Democratic Senate leader Chuck Schumer, speaking on the Senate floor on Wednesday, labelled Mr Trump a "co-conspirator" and demanded that the confirmation hearing for Supreme Court nominee Brett Kavanaugh, which is scheduled for early September, be delayed in the wake of Mr Cohen's plea.
Giuliani lashed out at Cohen on Tuesday, calling him a "devious little rat" and saying he had a history of lying.
By Wednesday morning, Trump's remarks were nowhere near as supportive.
In addition to pleading guilty to campaign finance violations, Cohen also admitted to tax and bank fraud.
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Cohen's lawyer Davis explained his client's about-face as "Michael fulfilling his promise.to put his family and country first and tell the truth about Donald Trump".
"Later on I knew".
The 2008 Obama campaign paid a $375,000 fine in 2013 to settle violations of a rule that contributions made 20 days before an election had to be reported within 48 hours.
Cohen said Trump directed him to make payments before the 2016 presidential election to women with whom he allegedly had affairs in order to buy their silence. Witch Hunt!' Trump wrote, referring to the counts on which the jury could not reach a unanimous decision.
Visibly crestfallen, the 51-year-old Cohen detailed how he made pre-election hush payments - "with the goal of influencing the election" - to two women alleging affairs with Trump: the porn star Stormy Daniels and Playboy model Karen McDougal.
Trump said that he did not believe that the hush-money payments amounted to a violation of campaign finance law, and suggested he was being unfairly targeted by the Justice Department.
Cohen told Judge William Pauley III that "in coordination with, and at the direction of, a candidate for federal office" he arranged payments to two women for their silence "for the principal objective of influencing the election".