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Paul Manafort is about to face another sentencing judge: Amy Berman Jackson

Paul Manafort's four-year sentence is infuriating some who call it lenient. But with another sentence underway, he could functionally still face life in prison. (Video: Jenny Starrs/The Washington Post)

The next federal judge to sentence former Trump campaign chairman Paul Manafort has already been thrust onto the national stage during the year-long run of special counsel cases.

U.S. District Judge Amy Berman Jackson, set to decide Wednesday whether she will add prison time for Manafort, is the same judge who was recently in the spotlight for the Roger Stone case.

She comes primed for her role by three decades as an attorney and judge dissecting sensitive political corruption and white-collar criminal cases in the nation’s capital.

Jackson brings to her position a veteran litigator’s patience, restraint and deep appetite for facts — and an unsparing ability to take apart attorneys or parties who test her intellect or betray her trust, said several lawyers who have practiced with, against and before her.

“She is smart, fair, always prepared, and tough,” said Reid ­Weingarten, who represented former Democratic congressman Jesse L. Jackson Jr. (D-Ill.), whom she sentenced to 30 months in prison in August 2013 for spending $750,000 in campaign funds on personal items. Weingarten praised the judge’s restraint in his and other cases and for “bending over backwards” to maintain ­order without being harsh.

The looming question Wednesday is whether any prison time Jackson might impose will overlap or be tacked on to the 47-month term Manafort received last week from U.S. District Judge T.S. Ellis III in Alexandria.

Ellis fueled controversy with the sentence, which fell far below federal advisory guidelines of up to 24 years that Ellis called “excessive” for Manafort’s bank and tax fraud convictions. The order came after Ellis’s brusque courtroom demeanor toward prosecutors and frequent interjections during Manafort’s summer trial moved the case briskly and also drew some criticism of the judge, who was appointed in 1987 by President Ronald Reagan.

Under the terms of Manafort’s plea agreement with prosecutors for special counsel Robert S. Mueller III, the 69-year-old faces up to a 10-year sentence from Jackson after admitting to conspiring to hiding millions he earned as an unregistered lobbyist for Ukrainian politicians over a decade and attempting to tamper with witnesses after he was charged.

Jackson, a 2011 Obama appointee, also has found that Manafort breached his plea deal by lying to prosecutors, including about contacts with a Russian aide, freeing prosecutors from their promise to consider recommending leniency in exchange for substantial help.

Federal judge finds Paul Manafort lied to prosecutors

In overseeing the Manafort case and the separate case of GOP operative and Trump adviser Roger Stone, who is accused of lying about his efforts to gather information concerning hacked Democratic Party emails, Jackson has given a master class in how to try high-profile cases, some colleagues on the bench said, by relying on preparation, discretion and a refusal to get drawn into side disputes.

During a tense February hearing in Stone’s case, Jackson kept lead defense attorney Bruce S. Rogow standing as she asked razor-edged questions about a photo of the judge on a Stone Instagram account that seemed to violate a limited gag order she had imposed on Stone to tamp down pretrial publicity.

“I’m not done with you,” Jackson said more than once to the men as she asked about an image that court security officials said appeared to place a gun sight’s crosshairs next to a photo of Jackson’s face. Stone, 66, said he wasn’t sure who had posted the image to his account but said he viewed it as a Celtic cross and apologized. Rogow proposed terms of a fuller gag order, which Jackson accepted.

“She doesn’t have any trouble with clarity,” said William D. Dolan III of Arlington, a former Jackson law partner and president of the Virginia State Bar, adding, “She will give both sides full opportunity to explain their position — but she isn’t going to give them the opportunity twice.

Jackson also showed that patience early in Manafort’s case before his plea, allowing a bail dispute to drag on for months while he was under house detention on unsecured bond. She also gave him a second chance after prosecutors complained that he violated a gag order by ghostwriting an op-ed in a Ukrainian newspaper.

The judge hammered Manafort only in June, after his indictment for attempted witness tampering — a bail violation that led to his jailing pending sentencing.

Manafort sentenced to 47 months in Virginia

Dolan recalled winning the first felony conviction of a Virginia sitting state judge as a special prosecutor with Jackson. It was the early 1990s, and many jurors in Norfolk had not seen a female trial lawyer, he said. “They went quite quickly from, ‘Who is this little woman’ to ‘Who is this sharp lawyer?’ ” Dolan said.

The Baltimore-born daughter of a U.S. Army-trained physician, Jackson, 64, earned bachelor’s and law degrees from Harvard University. She prosecuted violent and sex crimes at the U.S. attorney’s office in the District for six years, then in 1986 joined a law firm that became part of Venable.

Switching from aggressive prosecutor to aggressive white-collar defender came easily. In 2000, Jackson joined the law firm led by Robert P. Trout, which shared space with and would later add Plato Cacheris, whose national security or scandal-scarred clients included John Mitchell, attorney general under President Richard M. Nixon; Monica Lewinsky, the White House intern involved with President Bill Clinton; and U.S. spies Aldrich Ames and Robert Hanssen.

Jackson became a protege of Trout, who keeps a photograph of her 2011 investiture as judge on his wall, and whose current clients include former Trump communications director Hope Hicks and former congressman turned lobbyist Vin Weber (R-Minn.).

“Everything she does is very, very efficient,” Trout said in an oral history for the Historical Society for the District of Columbia Circuit, calling Jackson a “superb writer” who “pretty much” worked part-time 11 years for him while raising two children “although you wouldn’t know it from the amount of work that she would crank out.”

Jackson achieved her greatest prominence as a defense lawyer with Trout representing former Louisiana congressman William J. Jefferson on corruption charges in a complex, heavily litigated case — tried before Ellis — that is best known for the $90,000 in cash bribes found stuffed in the Democrat’s freezer and for a precedent-setting, separation-of-powers battle triggered by the 2006 FBI raid of his congressional office.

President George W. Bush himself stepped in at one point, ordering the Justice Department to seal all materials taken and stop reviewing them for 45 days.

“It’s not every day that a lawyer gets his motion granted by the president of the United States,” Trout said at the time — later confessing he was fed the line by Jackson.

Jackson’s rulings have cut across partisan or ideological lines. She blocked a $48 billion merger between health insurers Anthem and Cigna on antitrust grounds in 2017 and ruled for the mining industry in 2012 in halting an Environmental Protection Agency effort to revoke a permit for a “mountaintop-removal” coal mine in a closely watched regulatory case.

Jon B. Jacobs, a government attorney who prevailed in the Anthem fight before Jackson, called her meticulous and undaunted by complexity.

Having tried cases before judges “where there almost seemed to be some amount of resentment at the amount of paper pushed at the court,” said Jacobs, a Perkins Coie partner, he was impressed that “[Jackson] welcomed it because she knew she would have to learn it.”

Jackson also ruled against the Obama administration in some politically charged cases, finding that it had to turn over to House Republicans documents about the Justice Department’s botched “Fast and Furious” gun-tracking operation and make public records of whether the IRS improperly targeted conservative groups.

Before joining the bench, while on leave caring for her family in the late 1990s, Jackson commented on CNN and elsewhere on television on the O.J. Simpson murder trial, the Clinton Whitewater land-deal investigation and other cases.

In 2004, she co-wrote an op-ed in the Legal Times, arguing that Democratic presidential nominee Sen. John F. Kerry (Mass.) was the answer to the headline “Who’s Better for Lawyers?” over Bush.

Jackson walked back some of the article in answers during her Senate confirmation process to written questions from future Trump attorney general and then-Sen. Jeff Sessions (R-Ala.).

Sessions asked what she meant when she said the Bush administration had no commitment to the law, “view[ed] the legal system with contempt,” and secured office “through the legal process rather than the political process” after the disputed 2000 election.

Jackson conceded the language of the article was “too harsh” and the product of joint authorship on the eve of a closely contested election and said it “stands out among my 30 years’ worth of writings and public statements not only because of its tone, but because it was the only political piece that I played any role in writing.”

The Senate confirmed her appointment to the federal court on a 97-to-0 vote.

Clinical and shrewd in court, Jackson also shows a sociable side at the courthouse, as she did by donning a cowboy hat and singing a self-written parody of Frank Sinatra’s “My Way” in a packed federal courthouse ceremony in 2013 honoring a jurist known for his directness: former chief judge Royce C. Lamberth of the U.S. District Court for the District of Columbia.

She was formerly married to Darryl Jackson, a Washington lawyer and senior Republican appointee who served in Bush’s Commerce Department, after the two met as young prosecutors. One of their two sons credited them for his eclectic upbringing during an appearance on a national trivia television show, saying, “My mom is white, liberal and Jewish, and my dad is black, Christian and conservative.”

At her Judiciary Committee hearing, Jackson called herself the granddaughter of four immigrants and wore a necklace honoring her grandmother, a suffragist who became a citizen, raised three daughters and ran a business. On her Senate questionnaire, Jackson included her summer job between college and law school in 1976 working as a counter server at BIC’s Ice Cream in Cambridge, Mass.

“Of all the many things that can be said about me,” Jackson said, she hoped it would be “that I am a real person and I relate to other people from all walks of life.”

She added, “I think people are waiting for your rulings, and to rule clearly, because I think people need to understand them.”

Correction: A previous version of this article erroneously said that earlier in her career, now-Judge Amy Berman Jackson joined a law firm led by Robert P. Trout and Plato Cacheris in 2000. Trout shared space with Cacheris at the time, but Cacheris joined the firm in 2005. The article also erroneously described Jackson as the daughter, instead of the granddaughter, of four immigrants.

Alice Crites contributed to this report.

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