A series of rapid developments in one of the two cases against President Donald Trump's former campaign manager Paul Manafort indicate he's fighting an uphill battle against the special counsel Robert Mueller.

Over the last month, Manafort lost motions to dismiss the case, dismiss new charges against him, and suppress new evidence.

He was also accused of attempted witness tampering, hit with a new superseding indictment, and sent to jail.

The mounting pressure significantly raises the odds of Manafort's flipping on Trump.

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Paul Manafort, the former chairman and manager of President Donald Trump's campaign, is waging an uphill battle against the special counsel Robert Mueller in the Russia investigation.

Manafort is the defendant in two separate criminal indictments from Mueller's office — one in Virginia and one in Washington. He stands charged with over two dozen counts related to tax and bank fraud, conspiracy, obstruction of justice, making false statements, and failure to register as a foreign agent.

Manafort's lawyers have put up an aggressive defense against Mueller, who's investigating Russian election interference, but a series of developments over the last month in the Washington, DC, case indicate that the outcome for Manafort could be bleak.

First strike

Manafort's lawyers filed two motions to dismiss the Washington, DC, and Virginia cases, respectively.

Manafort's lawyers argued that Mueller had overstepped his authority by charging Manafort with crimes unrelated to Russian collusion, and that the scope of Mueller's mandate was overly broad.

In May, US District Judge Amy Berman Jackson struck down Manafort's motion to dismiss the Washington, DC, case.

Jackson concluded in a 37-page opinion that Manafort is an "obvious person of interest" for Mueller "given the combination of his prominence within the campaign and his ties to Ukrainian officials supported by and operating out of Russia, as well as to Russian oligarchs."

She added that charging him "falls squarely" within Mueller's mandate, pointing to an August 2017 memo that Deputy Attorney General Rod Rosenstein sent to Mueller outlining the scope of his investigative authority.

2nd strike

In early June, prosecutors asked the court to revoke Manafort's bail, accusing him and his longtime associate, the former Russian intelligence operative Konstantin Kilimnik, of attempted witness tampering.

Witness tampering "interferes with the proper functioning of the trial," and for that reason, judges tend to view it as a serious infraction, Jens David Ohlin, a vice dean at Cornell Law School who is an expert in criminal law, said in an earlier interview. "I'd expect the judge to come down hard on Manafort and revoke bail — assuming that Mueller has solid evidence of improper contact between Manafort and the witness."

Ohlin added: "What was he thinking?"

3rd strike

Robert Mueller. Alex Wong/Getty Images

Four days later, Mueller's office hit Manafort and Kilimnik with a new superseding indictment that charged them with conspiracy to obstruct justice and obstruction of justice related to their alleged attempts to influence witness testimony.

Manafort's lawyers fired back in a court filing later that night, arguing that prosecutors were using "heavy-handed tactics" to "corruptly persuade" two witnesses to perjure themselves at Manafort's September trial.

Adding that he didn't ask any witnesses to falsely testify or lie to the court, they asked the judge to toss out the two new charges against Manafort.

They also said Mueller publicly disclosed Manafort's alleged witness-tampering attempts to sabotage his request to be released from home detention.

Jackson refused to dismiss the charges.

4th strike

Less than a week later, Jackson sided with prosecutors on their motion to revoke Manafort's bail. He was subsequently sent to jail.

Legal experts said Manafort is now faced with the same decision as others in the Russia investigation: Should he flip?

"It's one thing to be a stand-up guy and not cooperate with prosecutors when you're out and about," said Jeffrey Cramer, a longtime former federal prosecutor who spent 12 years at the Justice Department. "That dynamic changes once the cell door locks and you spend your first night in prison."

Mueller's team first asked the court in December to revise the terms of Manafort's release after it learned that, while out on bail, he was ghostwriting an op-ed article about his lobbying work for Ukraine. Jackson issued a warning to Manafort at the time and did not penalize him.

"This is not about politics," she said after deciding to revoke his bail this month. "It is not about the conduct of the Office of Special Counsel. It is about the defendant's alleged conduct."

"Manafort did this to himself," Cramer said. "And now he's caught between a rock and a hard place, because he's going to be in jail for months."

5th strike

On Thursday night, Jackson dealt yet another blow to Manafort's case when she concluded that the FBI's search and seizure of a storage unit in Virginia belonging to Manafort's consulting firm was lawful.

Manafort's attorneys filed a motion earlier this year seeking to suppress the evidence that was seized, arguing that it should not be used in court because the initial search was conducted without a warrant.

Jackson wrote that the initial search was lawful because the FBI got permission to conduct it from a person listed as a lessee for the storage locker. She added that even if the initial search was unlawful, the seizure of the storage locker's contents was permitted because the search warrant the FBI obtained was based on an affidavit that spelled out why investigators believed Manafort was engaging in criminal activity.

Another key pillar of Manafort's lawyers' argument to suppress evidence was that the warrant itself was too broad and amounted to a carte blanche in violation of Manafort's Fourth Amendment right against unreasonable search and seizure.

Jackson on Thursday struck down that argument as well, writing that the warrant specifically instructed FBI agents to look for evidence related to the criminal activity related to his Ukraine lobbying work that Manafort is accused of engaging in.

Manafort is incarcerated at Northern Neck Regional Jail, in Virginia. His trial in the Virginia case is scheduled for July 25, and his trial in Washington, DC, is set for September 17.