Paul Manafort, Donald Trump’s former campaign chairman, is set to head back to court this week to be sentenced by Judge Amy Berman Jackson for conspiring against the U.S. and for a conspiracy to obstruct justice connected to his covert lobbying for foreign powers. He could face up to 10 years in prison for those crimes, on top of the 47 months he was given last week for fraud.

Manafort’s ever ballooning legal perils over the past two years have produced one potentially advantageous condition for him: the increasing sympathies of the man who possesses the power to pardon him.

It wasn’t long ago that Trump saw and berated Manafort as a nuisance and another expendable former adviser. In the first year of his presidency, Trump and his top aides went out of their way to downplay the former campaign chairman’s major role in the 2016 effort, with many on Team Trump privately blaming Manafort in part for federal investigators’ interest in the finances of the president’s family, and political and business associates.

According to sources close to the president, Trump never formed a rapport or comfort level of trust with Manafort during the campaign prior to his ouster. Trump viewed Manafort more as an irritating stage manager—one who brought with him a ton of baggage that would lead to President Trump and his White House team essentially disowning Manafort starting in early 2017. ( Manafort “played a very limited role for a very limited amount of time,” White House press secretary Sean Spicer told reporters in March of that year.)

Nowadays, however, Trump’s annoyance towards his onetime aide has been largely replaced with pity and attaboys. “I feel very badly for Paul Manafort and his wonderful family,” the president posted to Twitter in August. “‘Justice’ took a 12 year old tax case, among other things, applied tremendous pressure on him and, unlike Michael Cohen, he refused to ‘break’ - make up stories in order to get a ‘deal.’ Such respect for a brave man!”

The president’s public display of emotional support for Manafort is reflected in private discussions with close associates, who say that Trump has praised “Paul” for not being a “rat” or “coward,” as he views Cohen, and has repeatedly expressed agitation over Manafort’s jailing, sometimes likening him to a political prisoner.

“ The president’s public display of support for Manafort is reflected in private discussions, where Trump has praised ‘Paul’ for not being a ‘rat’ or ‘coward.’ ”

Trump has also encouraged it when his advisers or legal team have made public statements bashing the feds’ treatment of Manafort. “It’s good you got them [in the press] asking questions about Paul,” the president said last year to his lawyer Rudy Giuliani following one of Giuliani’s media appearances, according to two sources familiar with the comment. For instance, the Trump attorney had alleged in November that Mueller and his team were treating “Manafort like he’s a terrorist, incarcerating him before trial, solitary incarceration, and repeated questioning.”

Still, when pressed by reporters, President Trump has consistently dodged on whether or not he would pardon Manafort, the “brave man” he used to dislike and shun. And that potential pardon could be what saves Manafort from facing prison time.

The question now is whether Judge Jackson, a veteran litigator who was appointed by Obama in 2011, will add time to the years Manafort will already spend in prison for bank and tax fraud.

Last week, Judge Ellis in the Eastern District of Virginia, spurred controversy when he sentenced Manafort to just four years for the fraud charges—a significantly lower sentence than the federal guidelines, anywhere between 19 and 24 years in jail. Ellis last week called that “excessive” and instead handed down the drastically reduced sentence for for hiding and evading taxes on millions he made lobbying for Ukrainian political figures.

Manafort may not be so fortunate a second time. Jackson has shown little patience with Manafort’s antics thus far. When Mueller’s team accused Manafort of violating the terms of his bail by texting witnesses in the case, Jackson agreed, revoked his bond, and sent him to jail. And she ruled last month that Manafort intentionally lied to the Special Counsel’s Office and said federal prosecutors were no longer bound by the plea deal they struck with the former Trumpworld associate.

“In sentencing financial crime and corruption defendants, Judge Jackson, a former federal prosecutor, historically has demonstrated a sensitivity to the concern that social status and privilege alone ought not warrant leniency,” said Paul Pelletier, a former U.S. federal prosecutor, adding that Jackson is unlikely to take into consideration Ellis’s opinion in Virginia that Manafort led an “otherwise blameless life.”

“I am sure that [she]… recognizes that most federal defendants can make that same argument and that wealthy defendants shouldn’t be the only people who benefit from it,” Pelletier said.

Jackson, 64, spent six years as a U.S. attorney in Washington prosecuting violent crime before moving on to work as an attorney at Robert P. Trout and Plato B. Cacheris. There, she represented former Louisiana congressman William Jefferson on corruption charges. That case was tried in front of Ellis.

In 2013, Jackson sentenced Illinois congressman Jesse Jackson Jr. to two and half years in prison for misuse of campaign funds. Public prosecutors recommended four years. And recently, in 2017, citing antitrust grounds, she blocked the $48 billion merger of Anthem and Cigna.

Jackson is known in the legal world as a fair judge whose decisions often cross party lines. She is also overseeing the cases of Manafort’s right hand man during the 2016 campaign, Rick Gates, and Roger Stone, a Republican political operative who also worked closely with the Trump campaign.

In addition, Jackson sentenced former Skadden attorney Alexander Van Der Zwaan to 30 days in prison for lying to investigators about his interactions with Manafort’s associates. The sentence came as a surprise given Van Der Zwaan’s plea deal, cooperation with the Special Counsel’s Office, and his attorneys appeal for a simple fine. Jackson warned instead that “foreign interference in the democratic processes fundamental to our freedom”and that Van Der Zwaan’s sentence is “a message that needs to be sent.”

And last month Jackson put a gag order on Stone, preventing him from issuing statements to the media. That decision came after Stone uploaded a photo of Jackson on his Instagram account near crosshairs—a post that suggested she was biased against him.

“I’m not giving you another chance,” Jackson told Stone. “I have serious doubts whether you’ve learned any lesson at all.” Jackson threatened to send him to jail if he violated the order. Stone apologized to Jackson to which she responded: “Thank you, but the apology rings quite hollow,” she said. Based on his subsequent statements and actions, she said, “I don’t find any of the evolving and contradictory explanations credible.”

As Manafort’s case winds down in Washington, the special counsel’s office is expected to file a status report for Manafort’s number two during the 2016 campaign, Rick Gates, on Friday. Jackson is also overseeing this case.

Gates was one of the first Trumpworld associates to be indicted by Mueller. He pleaded guilty a year ago to two criminal charges—conspiracy and lying to the FBI.

Gates has cooperated extensively with the Special Counsel’s Office on various aspects of its investigation, including its interest in Manafort. His testimony contributed significantly to Manafort’s case in Virginia.

In January, Mueller’s team asked that the court postpone his sentencing because he was cooperating in “several ongoing investigations.”

During the campaign, Gates was also heavily involved in the Trump inaugural committee. He said in August during a grand jury testimony that he may have pocketed some of the money. Federal prosecutors are now probing that committee for possible misuse of funds and foreign donations.

The Special Counsel’s Office has also probed Psy Group, an Israeli-intelligence firm, for its connection to various individuals on the Trump campaign. Gates, according to The New York Times, sought online social media manipulation plans from the firm that could help Trump clinch the election.

If the Special Counsel’s Office issues a status report this week that says it is ready to move onto the sentencing phase with Gates, it could signal the winding down not only of the Manafort case, but the investigative phases of the inaugural committee and social media manipulation probes as well.

—with additional reporting by Adam Rawnsley