As a lobbyist, he developed a reputation for representing the unrepresentable, including former Philippine strongman Ferdinand Marcos, who was accused of torturing, abducting and killing thousands of opponents.
"Wow, what a tough sentence for Paul Manafort, who has represented Ronald Reagan, Bob Dole and many other top political people and campaigns", Trump tweeted on June 15. He was in the hot seat when Mr Trump eventually won the Republican nomination, and organised the Republican convention in July 2016.
Yanukovych's ouster in 2014 is relevant, the special counsel says, "because it explains Manafort's work for a different political party (the Opposition Bloc) and why his income later drops dramatically, which is relevant to the bank frauds that he later committed".
Manafort's defense team has filed a flurry of motions - to suppress evidence gathered from a Virginia storage unit, to challenge the mandate of the special counsel and to delay the trial - almost all of which it has lost so far.
Asonye told jurors the evidence would show Manafort hid "tens of millions of overseas income" to avoid paying taxes.
The indictment against Manafort says $75 million flowed through offshore accounts controlled by Manafort and his former business partner Rick Gates. He has since been co-operating with the investigation into Mr Manafort.
While the trial may touch on Manafort's communications during the campaign with his partners in the former Soviet bloc, the trial is not expected to focus on campaign ties to Russian Federation. Mueller is investigating Russian interference in the 2016 election, including potential coordination between the Trump campaign and Russia. Three Russian companies have also been charged.
Trump has repeatedly denounced the special counsel's investigation as a politically motivated "witch hunt" and denied there was any collusion with Moscow to defeat Democratic presidential nominee Hillary Clinton. His investigation is ongoing. And there's always the possibility that Manafort could take a plea deal during the trial if his defense falls apart, opting for a lighter sentence in exchange of telling Mueller's team anything he may know about possible collusion between the Trump campaign and Russian Federation.
Mr Manafort has filed a motion to have details oft hat work excluded from trial.
Legal experts said Manafort may be hoping to be found not guilty - or holding out hopes of a presidential pardon. "He has a right to consider it", Mr Giuliani told Reuters. Manafort has pleaded not guilty to those charges, as well.
Joshua Dressler, a law professor at Ohio State University, said the evidence against Manafort, 69, appeared strong but that he drew a favorable judge in the 78-year old T.S. Ellis, who is known to be tough on prosecutors.
Manafort was in charge of Trump's campaign when the NY real estate developer accepted the party's presidential nomination at the Republican National Convention in 2016.