A judge on Wednesday voiced serious doubts about former Trump campaign manager Paul Manafort’s lawsuit against special counsel Robert Mueller’s Russia probe. Manafort’s case is widely regarded as a Hail Mary move to avoid criminal charges.

Mueller, who is leading the investigation into Russian meddling in the 2016 election and contacts between Donald Trump’s campaign and Russian operatives, issued criminal indictments against Manafort last year for money laundering and conspiracy, among other charges, which were tied to Manafort’s work in Ukraine.

Trump’s former campaign manager had pleaded not guilty across the board, and started a separate civil lawsuit in January arguing that Mueller didn’t have the authority to bring those criminal charges because they’re not directly tied to Russian meddling in the 2016 election.

But at Manafort’s first case hearing on Wednesday, things didn’t seem to be going too well. “I don’t really understand what is left of your case,” federal Judge Amy Berman Jackson said, pointing to a court filing from Mueller’s team discussing its mandate.

If Manafort doesn’t win his civil suit, he’ll have to face criminal charges, which include a maximum jail time of 305 years combined. Manafort is the only Trump campaign figure charged as part of the Russia probe who hasn’t agreed to cooperate with Mueller.

Manafort looks unlikely to win his civil case

On Monday, Mueller’s team responded to Manafort’s January civil claim with a court filing that included new details about the authorities Deputy Attorney General Rod Rosenstein gave the special counsel in August.

As Vox’s Andrew Prokop wrote, Mueller’s filing said that Rosenstein had laid out the reasons he needed to investigate Manafort. Mueller wanted:

To learn about Manafort’s “ties” to and “interactions” with Russian and Russia-tied figures

To understand his “motives and opportunities to coordinate”

To “expose possible channels for surreptitious communications”

And finally, to “follow the money trail”

At the hearing on Wednesday, Berman Jackson, the judge presiding over the case, repeatedly expressed serious doubts about Manafort’s case in light of the new information that Mueller’s filing revealed.

Manafort’s team responded, saying that they were changing their complaint after the Mueller filing and are now arguing that Rosenstein overstepped his authority by approving Mueller’s mandate.

The legal argument uses the Administrative Procedure Act, which prevents federal agencies from writing or applying rules too broadly. Legal experts have called the argument a “Hail Mary” move.

At one point, Berman Jackson turned to Manafort’s lawyer Kevin Downing and asked, “Do you have one case that supports this?” The law Manafort is using for his lawsuit also expressly bars people from suing federal agencies over its application. “What am I supposed to do about that? Ignore it?” the judge also asked Downing.

Berman Jackson is also overseeing the criminal case against Manafort that includes 12 charges that are not directly connected to the election. Originally Mueller brought the charges against Manafort and his deputy, Rick Gates, but Gates subsequently pleaded guilty to lying to Mueller’s team, who let him off the hook on the other charges.

On Tuesday, Berman Jackson sentenced Manafort associate Alexander van der Zwaan, who was also being investigated by the Mueller probe, to a month in prison.

Wednesday’s hearing ended without the judge issuing a decision on Manafort’s civil case, although her doubts make it highly unlikely that Manafort will be able to avoid the criminal charges he faces.