Ex-Judge Jessica Arong O’Brien breaks down before getting 1 year in prison

With the looming threat of a prison sentence hanging over her head, the woman who once rose to become Cook County’s first female Filipino-American judge sobbed openly in a federal courtroom Thursday.

Jessica Arong O’Brien called herself “an embarrassment.” She said, repeatedly, that she was “stupid.” And, she exposed personal details behind the transactions more than a decade ago that led to her fraud conviction earlier this year.

When it was over, U.S. District Judge Thomas Durkin told O’Brien, “I still think you have difficulty admitting you did anything wrong.” But he credited O’Brien’s long record of public service before he sentenced her to a year and a day in prison.

The sentence was “not about you having been a judge,” Durkin said. Still, O’Brien worked as a lawyer when she committed her crimes. And Durkin said lawyers “have a special responsibility to follow the law.”

The sentencing on Thursday at the Dirksen Federal Courthouse brought a dramatic close to a case that likely would have gotten little attention had it not kicked off with the rare indictment of a sitting Cook County judge on federal fraud charges.

A jury found O’Brien guilty in February after prosecutors said she pocketed $325,000 in a mortgage fraud scheme that took place more than a decade ago, before she became a judge in 2012. She will now likely spend about nine months behind bars.

Despite her conviction early in the year, O’Brien didn’t leave the bench until September. She was paid $151,200 in 2018, according to a state comptroller database.

Defense attorney Steve Greenberg said O’Brien spent her life pursuing public and charitable endeavors “because she wanted to help others.” He called her life “a rags-to-riches story,” but she has now “fallen more than anyone that I have represented.”

Assistant U.S. Attorney Matthew Madden asked Durkin to send O’Brien to prison for two years, arguing that she abused the public trust when she worked at the state Department of Revenue, “regularly committing fraud while she worked there.”

“She did commit a crime, and it was blatant,” Madden said.

When offered a chance to speak, O’Brien sped up to a courtroom lectern and began to emotionally bare her soul to Durkin, telling him “I need you to know the truth.”

“I’m not innocent,” O’Brien said. “Obviously, the jury found me guilty, so I have to be guilty.”

Greenberg tried to intervene. Eventually, O’Brien broke down in tears. She insisted on pushing forward, but Durkin called a recess.

“It’s my courtroom,” Durkin said. “Just as you were a judge, it’s my courtroom.”

O’Brien’s sobs continued to fill the room during the break. When she regained her composure, Durkin returned to the bench, and O’Brien pressed on.

She called herself “an embarrassment” to people who elected her to the bench. She said her family “is forever marred from this,” and she repeatedly told Durkin, “I should have known better.”

Durkin said, “obviously, you’re in great pain.” But he said, “your family’s not forever marred.” He told the former judge she still has “plenty to contribute” to society. And, he noted a public service record that included mentoring young attorneys and starting scholarships.

“You lived a good life helping others,” Durkin said, “and that has to count for something.”