Paul Manafort faces between 19 and 24 years in prison for his conviction on tax and bank fraud charges in Virginia, one of two federal cases against him.

In a memo filed late Friday, Special Counsel Robert Mueller said that his office “does not take a position as to the specific sentence to be imposed here” but a presentence investigation report recommended a prison term of 235 to 293 months. If Manafort receives a sentence within that range, it would mark the harshest punishment received by anyone charged in the Russia investigation.

In the memo, prosecutors argued that the stiff sentence was warranted in the Virginia case because Manafort’s crimes, spanning millions of dollars and “the product of his planning and premeditation over many years,” were not isolated incidents but rather “routine” criminal behavior for him.

Legal experts said it’s unlikely the court will cut Manafort, former chairman of the Trump 2016 presidential campaign, much slack.

“There’s been been no remorse on Manafort’s part,” said Paul Pelletier, a former federal prosecutor. “There are times when the judge can reduce a defendant's sentence if they apologize and for example pay the taxes back. In this case, it looks as though the government has taken the position that he is an unrepentant crook."

A Virginia jury found Manafort guilty of eight federal counts of failing to report more than $16 million worth of income to the IRS from 2010 through 2014, failing to file a foreign bank account report in 2012, and lying on two loan applications.

After that verdict was in, Manafort pleaded guilty to conspiracy and witness-tampering charges in a separate case in federal court in Washington. But the judge in that case voided his plea deal this week after Mueller said Manafort had lied to investigators. T he sentencing memo Mueller issued Friday deals with the Virginia case, which has been ongoing for the last 15 months. However, the memo mentions the crimes in the DC case because “ they demonstrate [Manafort’s] concerted criminality”

Following his Virginia conviction, Trump called it a “very sad thing” that “has nothing to do with Russian collusion” and praised Manafort as a “good man.” As the case against Manafort in Washington has progressed, Trump has refused to rule out a pardon for his former campaign manager, saying he “wouldn’t take it off the table.”

At trial, prosecutors showed Manafort had hid millions in income from his consulting firm in offshore bank accounts in Cyprus and the Caribbean and used wire transfers from shell corporations to pay the tab for luxury goods and services like an ostrich leather jacket, high end audio-visual gear, and landscaping services at a residence in the Hamptons.

But when a revolution in Ukraine swept pro-Russian parties out of power, his consulting clients dried up and Manafort turned to tax and bank fraud to make ends meet. With the help of his accountant, he falsely claimed that nearly a million dollars in income was a loan in order to lower his tax bill. Manafort then lied on a loan application to Citizens Bank about the status of a Soho condo he used, and submitted a forged profit-and-loss statement from his consulting business to the Banc of California. The twin frauds netted Manafort roughly $4.4 million in loans.

Mueller’s office insinuated that Manafort had used his ties to the Trump campaign in order to push through a loan with Chicago’s Federal Savings Bank, flattering bank CEO Steve Calk with talk of a potential future role in the Trump administration. The prosecution produced emails that showed Manafort floated Calk’s name as a cabinet chief in the Army, Treasury Department, and Department of Housing and Urban Development. The jury, however, could not reach a consensus on the bank fraud counts related to Manafort’s loan applications at Federal Savings. Calk was never charged with a crime.

The decision on Manafort’s fate now rests with Judge T.S. Ellis, who delayed sentencing until the Washington court ruled on the plea deal breach.

“The special counsel’s office has given up on Manafort,” said Harry Litman, a former U.S. Attorney. “They are not trying to bring him back to the reservation even if he saw religion anew. I think this signals that the office is done with Manafort and the system is about done with Manafort. And I don’t think he’s made an attractive case for a pardon.”

In other Mueller and Russia-probe related developments, White House Press Secretary Sarah Sanders confirmed that she had met with the special counsel, saying in a statement that “I was happy to voluntarily sit down with them”; a judge issued a gag order for longtime Trump adviser Roger Stone and his attorneys, and a new court filing from the special counsel showed that in documented the self described “dirty trickster” communicated directly with Wikileaks with and Russian cutout Guccifer 2.0; new House Oversight Committee Chair Elijah Cummings said in a letter that two attorneys for President Trump may have lied to business officials about Trump’s formal personal attorney’s hush money to women on the then candidate’s behalf; New Jersey Attorney General Gurbir Grewal reportedly subpoenaed Trump's inauguration fund for “financial records” relate to fundraising in the state, and the Senate Finance Committee requested launched a probe into how the conservative Center for the National Interest think tank worked with confessed Russian agent Maria Butina.