Downing on Tuesday spent several hours firing questions at Gates to impugn his credibility and paint him as a liar, asking about everything from his extramarital affair in London and funds he embezzled from Manafort, to questions on whether he may have crossed the line by submitting personal expenses when he worked for Trump's inaugural committee.
In October 2016, for instance, Gates sent Manafort DMP's profit and loss statement (P&L) from January 1 through June 30 of that year, emails introduced in court Tuesday show.
As well as being a senior aide on Trump's election campaign, Gates served as the deputy chairman of the U.S. president's inaugural committee.
Downing seized on those admissions to try and cast doubt on whether the jury can trust Gates' claims that he only carried out the fraud alleged by prosecutors at Manafort's behest.
After saying Monday that he committed crimes with Manafort, including concealing offshore accounts to avoid reporting them to the US government at tax time and claiming false income to get loans, Manafort defense attorney Kevin Downing asked the witness, "This jury is just supposed to believe you after all the lies that you've told and the fraud you've committed?"
On Tuesday, the court was shown a series of emails, contracts and what prosecutor Greg Andres referred to as "fake invoices", in which Gates altered the template to show the name of a shell company instead of Manafort's.
Manafort, 69, is the first defendant to go to court to fight charges stemming from Mueller's investigation into Russian interference in the 2016 presidential election.
All three testified that Manafort and Gates failed to tell them about the foreign holdings in Cyprus.
Downing accused Gates of lying on expense reports to make trips to London and around Europe.
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The transfers would usually occur when Manafort made requests for Gates to initiate them-often through a list of to-be-sent wire transfers provided by Manafort to Gates via email.
On Tuesday, Gates was forced to answer questions about past infidelity, his embezzlement and what Manafort had directed him to do while in his employment.
In addition, Gates has admitted to other criminal conduct.
Gates acknowledged that he did for two months and that he took first-class flights and stayed in "fancy hotels" around Europe, but said the money came from bonuses rather than illicit gains.
During the testimony, Manafort did not stare Gates down as he did Monday.
Gates said prosecutors agreed not to pursue charges on those matters, and dropped a second indictment against him accusing him of bank and tax fraud.
Gates, who pleaded guilty in Special Counsel Robert Mueller's investigation in February, has testified that he helped Manafort falsify his tax returns, lie to banks to get loans and hide foreign bank accounts that Manafort used to receive payments from oligarchs for political work he did in Ukraine.
Mr Gates told jurors that he had been "tasked" by his boss "to determine how we could lower the taxes". Oh, and he says he did it all "at the direction of Mr. Manafort".
In other testimony, Gates recounted how he converted a PDF of a profit-and-loss statement to a Microsoft Word document so he could doctor it to inflate the business' income.
Gates also said that he did not report 15 foreign offshore bank accounts to the government. When Gates had prepared the transaction, he would run the final logistics by Manafort. "Mr Manafort had the same path". When the trial broke for lunch, Manafort looked back at his wife, sitting in the front row, smiled and winked at her, followed by a quick shake of his head, seeming to indicate he was unfazed by the morning's testimony.