Bijan Kian leaves the FBI Washington Field Office in Washington, Monday, Dec. 17, 2018. A one-time business partner of former National Security Adviser Michael Flynn, he has been indicted on charges including failing to register as a foreign agent.
Alexandria, VA CNN  — 

A federal judge on Thursday questioned whether there was enough evidence to uphold two guilty verdicts in a foreign lobbying case that stemmed from the Russia investigation and ensnarled a business partner of former Trump aide Michael Flynn.

At a procedural hearing in the Eastern District of Virginia, federal Judge Anthony Trenga grilled the prosecutors who successfully took Iranian-American businessman Bijan Kian to trial this summer. Kian was convicted of illegally acting as a foreign agent and conspiring to hide his work from the Justice Department — fallout from pro-Turkey lobbying he did with Flynn in 2016.

The judge repeatedly asked tough questions and pressed prosecutors for details proving that the Turkish government was “directly involved” in Kian’s lobbying campaign and said some evidence presented at trial suggested there was “a lack of direction or control” by Turkey. The judge’s questions got at the core tenets of the foreign agents laws that are in play in this case.

Defense attorney James Tysse said “no reasonable jury could ever conclude” that Kian was directed by Turkey and urged Trenga to toss both convictions or, at the very least, order a new trial. Trenga said he’d make a ruling “as soon as I can.”

Sentencing is scheduled for October 18.

If the judge throws out Kian’s convictions, it would be the second high-profile defeat for the Justice Department’s newly ramped-up effort to crack down on foreign influence, which was spun out from special counsel Robert Mueller’s investigation into Russian meddling. It would also tarnish the legacy of the Mueller probe, which uncovered the pro-Turkey lobbying scheme.

Both Kian and Flynn have ties to President Donald Trump: Flynn was the first national security adviser in the Trump White House and Kian advised the Trump transition team on national security matters.

Flynn pleaded guilty in 2017 to lying to the FBI about his Russian contacts and admitted in his cooperation agreement that the pro-Turkey lobbying violated federal laws for foreign agents. As a cooperator, Flynn was slated to testify against Kian at trial, but those plans fell apart at the last moment after a public and heated falling-out between Flynn’s new lawyers and the prosecutors.

But without Flynn as their star witness, prosecutors presented a slimmed-down version of the case, and the judge previously conceded that some of the evidence was “very speculative” and “very circumstantial.” Nonetheless, it only took jurors five hours to return two guilty verdicts.

It’s common for defendants in criminal cases to ask judges to drop the charges or throw out a jury conviction. It’s rare for a judge to grant this request, especially after the jury weighed in.

“Judges are, rightly, very reluctant to overturn a jury’s verdict,” said CNN legal analyst Elie Honig, a former federal prosecutor, who added that judges consider jury decisions as “sacred.”