While the second trial would highlight many of the same financial transactions as the first, prosecutors will also seek to prove that Manafort violated the Foreign Agents Registration Act when he conducted a multimillion-dollar lobbying campaign in the U.S. at the direction of Yanukovych. Manafort hired prominent U.S. firms like the Podesta Group and Mercury Public Affairs LLC to help him, as well as several prominent former European politicians.

At a pretrial hearing on Sept. 5, Manafort attorney Kevin Downing foreshadowed a trial defense on the lobbying charge, saying the Justice Department's oversight of the FARA regulations was vague and rarely enforced. Prosecutors, he said, can't prove that Manafort had any intent to violate the law, which is a requirement for conviction for that charge.

Former federal prosecutor Patrick Cotter said defendants often have a hard time grasping that they're running out of legal options.

"Guys who've gotten away with a lot of stuff before they get to prison" often show a lot of bravado, he said. "On the day of conviction they still believe there will be one more inning. It takes awhile before they realize there are no more innings."