Then, he pleaded guilty to six felonies associated with his personal business dealings -- including tax evasion and making false statements to a bank -- and two felonies for campaign finance violations.
On Friday, his attorneys requested, in a 29-page sentencing filing, that he be sentenced to "time served" citing his ongoing cooperation with prosecutors in multiple investigations, the toll on his family, and the president's personal attacks against him.
“In the context of this raw, full-bore attack by the most powerful person in the United States, Michael, formerly a confidante and adviser to Mr. Trump, resolved to cooperate, and voluntarily took the first steps toward doing so even before he was charged in this District,” Cohen’s attorneys wrote.
The president on Monday blasted Cohen for his request and said he should "serve a full and complete sentence."
“Michael Cohen asks judge for no Prison Time,” Trump complained on Twitter.
"You mean he can do all of the TERRIBLE, unrelated to Trump, things having to do with fraud, big loans, Taxis, etc., and not serve a long prison term? He makes up stories to get a GREAT & ALREADY reduced deal for himself, and get...his wife and father-in-law (who has the money?) off Scott Free [sic]. He lied for this outcome and should, in my opinion, serve a full and complete sentence."
Cohen was a longtime fixer for the president and managed both business and private dealings for Trump ranging from real estate to his alleged extramarital affairs. In his August plea hearing, Cohen directly implicated the president in hush-money deals with the two women who claimed to have had affairs with Trump, telling a court that he facilitated the deals "in coordination with, and at the direction of a candidate for federal office," referring to then-candidate Trump.
In his deal with the special counsel for lying to Congress, Cohen claimed that he continued to brief Trump and his family on the progress of a proposal to build a Trump Tower in Moscow until the deal was abandoned in June 2016 -- when Trump was close to securing the GOP nomination for president.
The president, who famously values loyalty, has taken personal offense to Cohen's cooperation with the special counsel. Before taking off for the G-20 in Buenos Aires, the president stopped on the White House South Lawn to sound off on Cohen as "weak" and a liar.
"He's a weak person. He's lying, very simply to get a reduced sentence," Trump said.
The president praised another longtime adviser, Roger Stone, for saying he would not testify against the president.
"'I will never testify against Trump.' This statement was recently made by Roger Stone, essentially stating that he will not be forced by a rogue and out of control prosecutor to make up lies and stories about “President Trump.” Nice to know that some people still have 'guts!'," the president tweeted.
Stone appeared on ABC's "This Week with George Stephanopoulos" on Sunday and said he would refuse to go against the president.
“There’s no circumstance under which I would testify against the president because I’d have to bear false witness against him. I’d have to make things up and I’m not going to do that," Stone said.
The president has complained extensively about the special counsel's work in recent weeks as the probe appears to be reaching its conclusion.
"Bob Mueller (who is a much different man than people think) and his out of control band of Angry Democrats, don’t want the truth, they only want lies. The truth is very bad for their mission!" Trump tweeted on Monday morning.
White House press secretary Sarah Sanders called the special counsel "the Russian Witch Hunt Hoax" in an official statement while the president was in Argentina and said it is "hopefully now nearing an end."
ABC News' James Hill contributed to this report.