But then came revelations that his longtime friend, David Pecker, the CEO of National Enquirer publisher American Media Inc., had been granted immunity from prosecution to provide information, followed by news that Trump Organization finance chief Allen Weisselberg, who had once worked for Trump's father, was cooperating as well.
Following previous reports that Weisselberg had testified before a grand jury earlier this year, the Wall Street Journal broke the immunity revelation on Friday.
The Manhattan district attorney's office and the Trump Organization did not immediately reply to CNBC's requests for comment.
Allen Weisselberg's immunity in Michael Cohen's investigation could spell trouble for President Trump. The payment to Daniels was reimbursement to Cohen by the Trump Organization as authorized by Weisselberg, who, the Journal reported, did not know the money was meant to pay Daniels. In April, Trump denied he knew anything about the Daniels payment. It sounds like Weisselberg is the kind of person who might be able to actually help prosecutors get to the truth, in theory, here.
Experts said the deals were a sign Weisselberg, Pecker and Howard faced criminal exposure because the government did not grant immunity lightly. "I think everybody would be very poor", the president said in an interview with Fox News.
"The only reason to do that would be to hide the nature of the payment and to make it tax deductible", Ware said.
Money and loyalty also drove Cohen to enter guilty pleas this past week in a spinoff from the swirling investigations battering the Trump White House.
Trump, who had previously said that Cohen would remain loyal to him and "never flip" mocked his former lawyer, calling his professional competence into question.
The testimony implicated Trump in the crime, legal analysts said, although few believe the sitting president could be indicted.
For years, Cohen was a fixture in Trump's orbit.
CNN recently asked a wide-range of Americans living in northeast Pennsylvania - Republicans, Democrats, and independents - for their opinions on President Donald Trump following the legal developments surrounding Paul Manafort and Michael Cohen, two men deeply tied to the president.
Mr Cohen said on the tape that he had already spoken about the payment with Mr Weisselberg on "how to set the whole thing up". It's the most direct accusation of wrongdoing leveled against Trump to date - the sort of allegation that, if borne out by the evidence, could result in felony charges against any candidate short of a sitting president.
Democratic forces hoping to nail Trump for alleged Russian Federation collusion are now pinning their hopes on Michael Cohen, who was convicted on eight counts tax fraud.
However US intelligence officials have also said that North Korea may have increased production of fuel for nuclear weapons at multiple secret sites, according to an NBC News report in July.