Paul Manafort now has two options: Flip or put his “whole life in Trump’s hands”

On the campaign trail, President Trump pledged to hire “the best people.”

Lately, they’ve been “the best” at racking up felony convictions.

Take Trump’s former campaign chairman Paul Manafort. Fresh from guilty verdicts on eight counts of financial crimes in Virginia, Manafort faces seven more in a trial due to kick off September 24 in Washington, D.C., in what legal observers call yet another a powerful case against him.

“When I look at these charges, I see charges that are very easy to prove,” said Renato Mariotti, a former federal prosecutor. “He’s probably going to lose.”

Read: Rick Gates says he did crimes with Paul Manafort and stole his money

If he goes to trial, that is. A report in The Wall Street Journal on Monday said Manafort recently launched a short-lived bid to reach a deal to plead guilty, which eventually sputtered.

Now, with his freedom hanging in the balance, here’s what’s next for Paul Manafort, President Trump’s embattled former campaign chairman.

While some observers took the Journal report as a sign Manafort is preparing to reach a cooperation agreement with special counsel Robert Mueller, whose primary mission is investigating Russian interference in the 2016 election, others argued it’s too soon to say.

The details revealed so far indicate he may just have been trying to nail down a limited deal to plead guilty and avoid his next trial, but without a pledge to cooperate, according to former prosecutor Barbara McQuade.

“You can plead guilty without flipping,” McQuade told VICE News.

Manafort may be hanging tough for a pardon from President Trump, who has expressed sympathy for his old campaign chairman, observers have said.

Read: Mueller’s team paints Manafort as a “wildly successful” political operative twisted by greed in closing argument

But Seth Waxman, a former federal prosecutor in D.C., said that after Manafort’s conviction last week, he’ll likely begin to calculate that working with Mueller may seem like a safer bet than waiting around for a pardon from the ever-unpredictable Trump, who may face political pressure not to issue that pardon later on.

“If you put a gun to my head, I’d say I think he’ll flip,” Waxman said. “Otherwise, he’s putting his whole life in Trump’s hands.”

If he doesn’t restart talks and reach a deal with Mueller’s team soon, however, he’ll soon face a second round of courtroom drama that legal observers told VICE News appears likely to result in yet another conviction.

“The case in DC looks as strong as the case in Virginia,” Waxman said.

This time Manafort’s being charged with:

• Failure to register as an agent of a foreign government
• Filing false registrations as an agent of a foreign government
• Making false statements
• Obstruction of justice
• Conspiracy to launder money
• Conspiracy to defraud the U.S. through a series of financial measures

Manafort’s last trial focused on how he handled tens of millions he earned while working as an political adviser for the former president of Ukraine. Prosecutors said he’d funneled over $60 million through a web of offshore companies, and failed to pay taxes on over $15 million.

His next trial will cover some of that same financial ground for the conspiracy charges, but it will also take aim at the nature of the political work Manafort did to earn all that money.

The charges stem from the years before Manafort signed up to run Trump’s campaign, when he worked as an adviser for former president of Ukraine, Viktor Yanukovych.

Manafort was credited as the architect of Yanukovych’s improbable rise from political oblivion, following accusations he’d tried to steal the country’s 2004 election, to winning Ukraine’s 2010 presidential election.

After his boss won power, Manafort switched from campaign adviser to helping Yanukovych form policy.

“After he helped them win elections, Paul earned so much trust from Yanukovych and the decision-makers in the Party of the Regions that they looked at him as something of a wizard,” Oleg Voloshyn, former spokesman for Yanukovych’s foreign ministry, told VICE News. “Initially, they listened to almost everything he advised.”

And Yanukovych’s regime was embroiled in controversy. The new president faced harsh criticism from Europe and the U.S. over the imprisonment of his main rival in the 2010 election, Yulia Tymoshenko, immediately after the vote.

Manafort swung into action to try to limit the fallout and smooth relations with the West, according to the testimony of Manafort’s ex-right hand man, Rick Gates, during his trial in Virginia.

But according to prosecutors, Manafort’s secretive attempts to improve Ukraine’s image broke the law. He set about organizing a shadowy group of former top European politicians dubbed “The Hapsburg Group,” to influence not only European governments, but also to lobby in Washington DC, according to the charges against him.

Read: Trump Org money man Allen Weisselberg could be the president’s next nightmare

Doing so violated a decades-old rule called the Foreign Agents Registration Act, according to prosecutors.

While that law has been very rarely enforced in the past, Manafort won’t simply be able to argue that he shouldn’t be punished because others got away with breaking the rules, Mariotti said.

“If you get pulled over by a cop, and your argument is, ‘But everyone else was speeding,’ you’re still going to get a ticket,” Mariotti said. “The cop probably won’t buy that.”

The fact that Manafort faces two trials, instead of just one, is a torment of his own devising, legal observers pointed out.

Manafort had the option of pulling the two sets of charges filed in separate jurisdictions (one batch in DC, and the other in his home state of Virginia) together, but opted to allow them proceed separately for reasons that remain unclear.

Whatever his thinking, the resulting twin-trial strategy could end up doubling his legal jeopardy if the judges slap him with two sequential prison sentences, said Charles A. Intriago, a former prosecutor and money laundering expert.

“It didn’t make any sense,” Intriago said. “It makes me wonder what he was thinking.”

Read: Paul Manafort spent decades pushing the envelope of what’s legal. His trial strategy is just as high-risk.

Manafort, who has sought to delay both trials on multiple occasions, may be working a strategy that extends outside the courtroom. Observers have said he may be attempting to position himself in the best possible position for a pardon from Trump.

Opting for two separate trials might have been about trying to delay the courtroom action until after the midterm elections, scheduled for this November, when a pardon might become politically easier for Trump, Mariotti said.

“At this point, I don’t see any advantage for him to continue to fight,” Mariotti said. “I think that he’s clearly angling for a pardon.”

Cover: Paul Manafort arrives for a hearing at US District Court on June 15, 2018 in Washington, DC. (Photo: MANDEL NGAN/AFP/Getty Images)