Since his indictment in January 2019, Roger Stone’s path to Thursday’s sentencing hearing has been anything but ordinary. But given his long history as a political dirty trickster, perhaps it should come as no surprise that his legal woes have followed an equally unusual trajectory.

The veteran Republican operative was found guilty in November of obstructing justice, witness tampering and five counts of lying to Congress. His pre-trial proceedings were largely marked by his out-of-court statements, triggering progressively tighter gag orders. His trial featured testimony from a comedian who repeatedly invoked characters from The Godfather: Part II.

But less than two weeks before his sentencing, the most consequential twist: a disagreement between line prosecutors and the Justice Department’s political leadership over Stone’s sentencing recommendation, the fallout from which continues to resonate throughout Washington. And looming over it all? A possible pardon from his longtime friend, President Donald Trump, who on Tuesday again expressed sympathy for Stone.

The two go back decades, and at his trial late last year, prosecutors connected Stone’s crimes with an effort to protect Trump. Stone, 67, has previously taken credit for persuading the president to get into politics and once served as an adviser to Trump’s presidential campaign.

After formally leaving the campaign in late 2015, Stone remained in touch with multiple senior advisers to Trump — and Trump himself. According to testimony and evidence presented at his trial, Stone became the campaign’s informal point-person on all things WikiLeaks — a relationship that underpinned lies he eventually told during sworn testimony before the House Intelligence Committee in September 2017. Stone was convicted of misleading the committee on several key elements of their probe into Russian meddling in the 2016 election, including communications he had with the Trump campaign about discussing WikiLeaks dissemination of damaging documents stolen from Democrats during the campaign.

Stone was arrested in a pre-dawn FBI raid on his Florida home on Jan. 25, 2019. In the 10 months leading to his trial, Stone repeatedly made inflammatory comments about the judge overseeing his case and the prosecutors who brought charges. After posting an image to social media with U.S. Judge Amy Berman Jackson apparently shown in the crosshairs of a firearm scope, she issued a gag order preventing him and his legal team from speaking publicly about the case.

At trial in November, jurors found him guilty on all seven counts. But in the weeks leading up to his sentencing hearing, Stone’s lawyers twice made last-ditch efforts to get a new trial by raising issues with at least two jurors.

Last week, unsealed court documents revealed that Judge Jackson denied a previous sealed motion for a new trial filed by Stone’s defense team earlier this month involving a post-trial objection to one of the jurors. The individual disclosed during the jury selection process that they had a legal background and had worked for the IRS. A second sealed motion for a new trial was filed by Stone’s attorneys last Friday citing alleged jury misconduct. Details of both the request and the Justice Department’s subsequent opposition to their motion are mostly unknown while under seal.

In a conference call with Stone, his defense team and two DOJ prosecutors on Tuesday, Jackson said that she has decided not to delay Stone’s sentencing in light of the defense’s latest bid for a new trial. But, Jackson said on the call, “I will ensure that the execution of sentence and the deadline for the filing of a notice of appeal will be deferred to ensure that the defendant has had the benefit of the ruling on the motion before filing any notice of appeal.”

Since his conviction, the national interest in Stone’s legal fortunes has waned. But that changed earlier this month when Trump unexpectedly weighed in on a sentencing recommendation filed by the four Justice Department prosecutors running Stone’s case. Last week, those prosecutors told the court that Stone’s crimes and his out-of-court conduct warranted a prison term of seven to nine years.

Within hours of their filing that sentencing recommendation, at 1:48 a.m., a message appeared on the president’s Twitter feed: “This is a horrible and very unfair situation. The real crimes were on the other side, as nothing happens to them. Cannot allow this miscarriage of justice.”

The next day, a senior Justice Department official told reporters that “the department was shocked to see the sentencing recommendation,” and that “the department will clarify its position later today at the court.”

That statement prompted all four Justice Department prosecutors who signed onto the sentencing memorandum to withdraw from Stone’s case in protest. One of those prosecutors resigned from the department entirely.

Later that day, a new prosecutor on the case filed an amended memorandum arguing that the previous recommendation of seven to nine years “would not be appropriate” — and instead “defers to the court as to what specific sentence is appropriate,” but implored Jackson to take into consideration Stone’s “advanced age, health, personal circumstances and lack of criminal history in fashioning an appropriate sentence.”

In the aftermath of the sentencing controversy, Attorney General William Barr told ABC News Chief Justice Correspondent Pierre Thomas that Trump “has never asked me to do anything in a criminal case,” but he should stop tweeting about certain Justice Department cases.

“I think it’s time to stop the tweeting about Department of Justice criminal cases,” Barr said, adding that the tweets “make it impossible for me to do my job.”

On Tuesday, ABC News reported that Barr had told people close to Trump that he is considering resigning over the tweets.

Regardless of the sentence Judge Jackson imposes on Stone, a wild-card factor could render the terms inconsequential: a pardon from Trump — which he has not ruled out. On Tuesday, the president expressed sympathy for his longtime confidant and downplayed Stone’s role in his campaign.

“I think Roger Stone’s been treated unfairly,” Trump said.

Asked whether he believes Stone deserves to serve time in prison, Trump replied, “you’re going to see what happens, let’s see what happens.”