Paul Manafort has breached the terms of his plea agreement, “intentionally” misleading Robert Mueller and his grand jury since pleading guilty as part of the special counsel’s Russia probe. That’s according to a federal judge, Amy Berman Jackson, who, on Wednesday, found that Donald Trump’s former campaign chair had lied to the special counsel’s office on multiple occasions, including about a meeting with Russian operative Konstantin Kilimnik in 2016 that has seemingly become central to the Mueller investigation. “[Mueller] has established by a preponderance of the evidence that the defendant intentionally made multiple false statements to the F.B.I., the O.S.C., and the grand jury concerning matters that were material to the investigation: his interactions and communications with Kilimnik,” the judge wrote.

As a result, Mueller’s team is “no longer bound by its obligations” under the plea agreement it struck with Manafort last year. And Manafort, who is already serving his jail sentence, cannot change his guilty plea. Manafort’s only hope for leniency, then, lies in his former boss, who still wields pardon power.

Manafort was among the first to be indicted in the Mueller investigation, and was convicted in August on eight counts primarily related to tax- and bank-fraud charges. He cut a cooperation agreement with the special counsel soon after to avoid a second trial, but has evidently violated its terms—most notably in his apparent efforts to mislead investigators about the nature of his relationship with Kilimnik, whose August 2016 meeting with Manafort has emerged as a key episode in the inquiry. According to The Washington Post, prosecutors believe that Manafort—along with his deputy, Rick Gates—may have exchanged information with Kilimnik at the meeting related to Russia and the Trump campaign. Investigators believe the men may have discussed polling data at the shady rendezvous, as well as Ukraine, a key Russian interest and where Manafort had worked for years, the Post reported on Tuesday.

It’s not clear why Manafort would lie about the interaction and other matters after entering his guilty plea with Mueller, but it almost certainly means he’ll face an even stiffer prison sentence—unless, of course, his reticence is rewarded with a pardon. Trump, whose cries of “witch hunt” have devolved to background noise, had previously expressed sympathy for his former campaign chairman, and praised him for refusing to “break” à la Michael Cohen. “Such respect for a brave man!” Trump tweeted after Manafort’s conviction in August.

The president has continued to hint at a potential pardon, including in November, when he told the New York Post that he “wouldn’t take it off the table” after prosecutors first accused Manafort of breaking his plea agreement. Perhaps this was Manafort’s play all along, or perhaps it’s a happy side effect. Either way, after Jackson’s ruling Wednesday, it’s likely his last, best hope.

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