Michael Flynn, the former national security adviser for President Donald Trump who resigned in disgrace after lying to Vice President Mike Pence about his contacts with Russian officials and later pleaded guilty for lying to FBI agents, has a new legal headache that could well send him to prison: The judge in his case is on the brink of sentencing Flynn to prison for contempt and perjury.

Politico reports:

“A federal judge is signaling that he might pursue perjury or contempt charges against former national security adviser Michael Flynn over his effort to abandon a guilty plea to a charge of lying to the FBI.

“The Justice Department moved last week to drop the prosecution of Flynn launched by special counsel Robert Mueller, but U.S. District Court Judge Emmet Sullivan slammed the brakes on that effort by announcing Wednesday evening that he is appointing a former federal judge to argue against the government’s unusual bid to dismiss the case against an ally of President Donald Trump.”

The appointment of a former judge to provide a counterpoint to the DOJ request that all charges against Flynn be dropped is a direct slap in the face of Attorney General William Barr, who has been trying for months to make sure that Flynn walks free despite his lies.

At question is the timing of the Justice Department’s motion to dismiss, is “virtually unheard of,” according to Jonn Gleeson, the former judge chose by Judge Sullivan. In an op-ed he co-authored for The Washington Post, Gleeson added:

“There has been nothing regular about the department’s effort to dismiss the Flynn case. The record reeks of improper political influence.”

Ironically, Barr’s move to clear Flynn may wind up placing the former Trump official in even greater legal jeopardy.

Flynn has said on more than one occasion under oath and in open court that he did indeed lie to the FBI:

“In December 2018 — at a hearing where Flynn was originally expected to be sentenced by Sullivan — Flynn reaffirmed his guilty plea. He also said he was satisfied with his lawyers from the prestigious firm of Covington & Burling and that he had no concerns that any information relevant to his defense was being withheld.”

At the moment, it appears that the only thing that will possibly save Flynn from time behind bars is a presidential pardon, but such a move carries political risk for Trump this close to an election.