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Could January 6 be the infamous Roger Stone's political swan song?

As part of his Capitol riot plea deal, Oath Keeper Joshua James must cooperate with prosecutors. That could be bad news for longtime Trump associate Stone.

On Wednesday, Joshua James, the leader of the Alabama Chapter of Oath Keepers, pleaded guilty to seditious conspiracy and obstruction of Congress for trying to prevent the peaceful transfer of power after the 2020 election. The Oath Keepers — a group of anti-government extremists — were among those who stormed the Capitol on Jan. 6, 2021. As part of his guilty plea, James agreed to cooperate with prosecutors, including providing testimony to a grand jury.

This could spell trouble for longtime Trump associate Roger Stone, who was linked to James in the hours and days leading up to the insurrection. To be clear, there is no publicly available language directly tying Stone to violence, and we have no way of knowing what James will tell prosecutors. And Stone has a knack for getting out of tight spots — especially when he has friends in the White House. It's been a long, wild ride. But could accountability finally be coming for the ignominious, infamous “dirty trickster”?

Stone has a knack for getting out of tight spots — especially when he has friends in the White House.

The Washington Post recently obtained a video showing that a few hours before the Jan. 6 attack, James was in Stone’s suite at the Willard hotel in Washington. James served as Stone’s bodyguard, according to reporting from Politico and others.

It's never good when one of your associates is cooperating with prosecutors as part of what “has become one of the largest, most complex, and most resource-intensive investigations” in American history, according to Attorney General Merrick Garland. This is particularly true for Stone, who was involved in the efforts to protest and possibly overturn the 2020 election. After Trump’s defeat in November 2020, Stone “moved quickly” to help draw thousands of angry Trump supporters to the nation’s capital, according to the Washington Post, which also reported he privately strategized with former national security adviser Michael Flynn and “stop the steal” rally organizer Ali Alexander and used an encrypted messaging app to communicate with another Oath Keepers leader, Stewart Rhodes, later in January. Rhodes is currently awaiting trial on charges of seditious conspiracy. (He has pleased not guilty.)

Stone also told associates that he remained in contact with Trump during the days and weeks before the insurrection, interesting context for investigators continuing to look into Trump’s own role in January 6. (Stone told the Washington Post: “Any claim, assertion or implication that I knew about, was involved in or condoned the illegal acts at the Capitol on Jan 6 is categorically false and there is no witness or document that proves otherwise.”)

Because of how the Constitution defines treason, seditious conspiracy is the closest approximate charge for prosecutors in cases like James': “Treason against the United States shall consist only in levying War against them, or in adhering to their Enemies, giving them Aid and Comfort.”

Courts have narrowly defined “enemies” to mean countries Congress has declared war against. Seditious conspiracy, on the other hand, includes “conspiring to overthrow, put down, or destroy by force the Government of the United States... or by force to prevent, hinder, or delay the execution of any law of the United States.” What makes the charge of seditious conspiracy so serious is the requirement of force. Indeed, James admitted to conspiring with “others to oppose by force the lawful transfer of presidential power.”

Only recently, with the indictment of Rhodes and others on Jan. 13, has the DOJ begun charging seditious conspiracy. James’s guilty plea is the DOJ’s first seditious conspiracy conviction, but there are of course many other charges that can and have been used during the investigation. Prosecutors have plenty of options when meting out accountability.

It’s important to understand how these investigations work. As Garland explained in a speech in January, prosecutors begin by “laying a foundation.” They “resolve more straightforward cases first because they provide the evidentiary foundation for more complex cases. Overt actors and the evidence they provide can lead us to others who may also have been involved. And that evidence can serve as the foundation for further investigative leads and techniques.”

As part of his plea, James must cooperate with prosecutors. And thus the spotlight could turn to Roger Stone.

This is not Stone’s first — or third — brush with political notoriety. Indeed, his legacy has been built in large part on his willingness to push ethical boundaries with seeming impunity. As a 19-year-old, Stone worked on behalf of Richard Nixon’s Committee to Re-Elect the President to distribute pamphlets from a fake left-wing group bashing a Democratic presidential candidate as insufficiently liberal. Stone also admitted to Congress that he faked a contribution to a socialist party to try to sabotage a rival candidate.

This is not Stone’s first — or third — brush with political notoriety.

More significantly, Stone has taken credit for masterminding the so-called Brooks Brothers Riot of 2000, which bears a striking resemblance to the Jan. 6 insurrection. (The extent of Stone’s exact role in the planning of the Brooks Brothers riot remains a matter of dispute.) In that "riot," a group of Republican protesters descended on a government building in Miami to protest and perhaps stop the recounting of presidential ballots. The protest was disruptive enough to shut down the manual recount. And then the Supreme Court, in Bush v. Gore, put a stop to the recounting altogether.

After the Jan. 6 protest turned into a bloody riot, however, Stone evidently panicked. As a violent mob ransacked the Capitol, he packed his bags and reportedly told an aide, “I really want to get out of here” adding that he thought the riot would be “really bad for the movement.”

After the riot, he lobbied Trump to enact the “Stone Plan” — a blanket pardon to shield himself and Trump’s allies in Congress from prosecution for any efforts to overturn the election more generally. Stone had good reason to think Trump would offer such a pardon. After all, Trump pardoned him after he was indicted (and convicted) on charges of lying to Congress, witness tampering and obstruction of justice. What’s one more pardon between friends?

But according to The Washington Post, White House counsel Pat Cipollone “thwarted” the Stone Plan, prompting Stone to write to an associate: “See you in prison.”

Stone insists that he had nothing to do with the violence. But if Joshua James has a different story to tell, Stone may not be able to wriggle away from prosecutors this time. And meanwhile, the investigation could be moving closer into Trump’s inner circle.