The man who led Chicago Police Officer Jason Van Dyke’s defense team found himself back in a courtroom Tuesday, asking a panel of judges to reverse an imprisoned Chicago cop’s conviction.

But this time, lawyer Dan Herbert wasn’t fighting for Van Dyke. Instead, he was working for Marco Proano, who last year became the only Chicago Police officer in recent history to face federal prison time for an on-duty shooting.

Proano, 43, is in a low-security prison in Loretto, Pennsylvania, according to the Bureau of Prisons. U.S. District Judge Gary Feinerman sentenced him to five years behind bars after a jury found him guilty in August 2017 of using unreasonable force when he wounded two teenagers in an on-duty shooting in December 2013.

Even though Proano’s trial preceded Van Dyke’s by roughly a year, it still seemed to play out under the shadow of Van Dyke’s looming prosecution. That’s because the two men share a defense lawyer — Herbert.

Herbert found himself arguing Proano’s case Tuesday before a three-judge panel on the 27th floor of the Dirksen Federal Courthouse. A portion of the hearing was sealed while Herbert and prosecutors argued whether prosecutors were wrongly exposed to legally protected statements made by Proano — so-called Garrity material.

When the courtroom doors opened, Herbert insisted Proano’s conviction should be reversed. He said prosecutors improperly pointed to Proano’s local training — as opposed to nationally or widely used policies — as evidence that he willfully violated the teens’ federal rights.

“It can’t be the sole basis to determine willfulness,” Herbert said.

Judges on the panel said they had trouble following his argument, though. At one point, Appellate Judge David Hamilton told Herbert, “I understand your words. I don’t understand your logic there.”

Assistant U.S. Attorney Georgia Alexakis later said other evidence, beyond Proano’s training, supported the notion that Proano knew what he was doing was “plainly wrong.” In fact, she said, Proano’s behavior violated common sense.

Proano and his partner arrived at 95th and LaSalle on Dec. 22, 2013, to back up fellow officers who had already crossed paths with a stolen Toyota packed with at least six teenagers.

By the time Proano arrived, the driver of the car had fled. A BB gun later fell out of the car, and Proano watched as the car suddenly began to reverse with one teen hanging out of a window. Another teen had lunged forward from the back seat, thrown the car into reverse and pushed the gas pedal with his hands.

No one was in the car’s path.

What happened next was caught on a police dashcam video. Proano can be seen in the video stepping forward, holding his gun sideways. Seconds later, he steps backward as the car reverses into view. Proano then lifts his gun again with both hands, upright, and a flash can be seen as he appears to open fire.

Proano fired 16 times in nine seconds. One teen was wounded in his left hip and right heel. The other suffered a shoulder wound. Proano has said he pulled the trigger to protect the teen hanging out the window.

Unless his appeal is successful, Proano is not expected to emerge from prison until May 2022. It is not clear when the appellate court will rule.

Meanwhile, Herbert’s other high-profile client still faces sentencing. A state court jury found Van Dyke guilty earlier this month of second-degree murder and 16 counts of aggravated battery for the shooting death of Laquan McDonald.

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