A grand jury in Manhattan won’t reconvene until Monday (NZT) to discuss the case which could lead to an indictment of former United States President Donald Trump.
It’s over hush money allegedly paid to adult film star Stormy Daniels who says she had an affair with the former president, a claim he denies.
"It's hard for me to say what they're going to charge him with specifically in the strength of the witnesses that they may advance toward him," Brewster said in Thursday's interview.
"But I can tell you that the statements that he's been making in the press don't comport with the facts as I understand them and if he has that defence, I think he's at great risk of being convicted."
Speaking with O'Brien on Friday morning, a former financial prosecutor for the New York district attorney’s office, Catherine Christian, said she doesn't necessarily agree with Brewster that Trump is at greater risk of being convicted. However, she does agree that "every statement a defendant makes publicly" can impact the case.
"It's going to be a difficult case," Christian said.
"What's fortunate for Donald Trump is the main witness he has against him, Michael Cohen, has been convicted of lying.
"His [Trump's] defence attorneys will have a gift because they will be cross-examining Mr Cohen about that conviction and - I was a former prosecutor - if I had a witness who every time I turned on the TV, I saw him speaking about the case, I would be cringing.
"Mr Cohen likes attention and he keeps speaking about the case publicly and he probably should stop that."
Listen to the full interview between Catherine Christian and Tova above.
You can also download the full interview on the Tova podcast, and listen on the go.