From Judge to Prison: Jessica O'Brien's Fall and Rise
When an English teacher in the Philippines told a teenage Jessica O’Brien she would “never succeed in America” because of her accent, she had no idea that girl would one day preside over a Cook County courtroom.
I have been wanting to talk to Jessica O’Brien for over a year. She and I have become friends, bouncing ideas off each other about criminal justice reform and re-entry. I’ve had FBI agents on this podcast. I’ve had a warden. But I had never had a judge. Jessica was not just any judge either. She was the first Filipino-American judge elected in Cook County. Before that, she was a special assistant attorney general for the Illinois Department of Revenue.
And here’s what makes her story stand out: when the federal government came after her, she refused to plead guilty. Only 3% of federal defendants go to trial. Jessica went to trial. She lost. She got a year and a day. And she is still fighting to get that conviction vacated.
From the Philippines to Atlantic City
Jessica came to America at 16 years old. Her mother was a doctor who had immigrated years earlier, doing her residency in the Bronx and working in underserved communities. Jessica’s parents split up. Her sister went to America with their mom. Jessica stayed in the Philippines with her father.
“I was afraid to come to America,” Jessica told me. “My English teacher criticized me and said, ‘You’re going to America. You have horrible English. You will never succeed in America. You’ll be nobody.’ And I still remember that to this day.”
But she also knew staying in the Philippines meant limited options. Her family was not wealthy. She went to Catholic school with rich kids whose families owned hospitals and shipping lines. Her dad had a small business. She knew she had to take the chance.
“I sucked it up and I came to America.”
What she didn’t share publicly for years was that she experienced sexual molestation as a young person after arriving. Her mother didn’t believe her. That trauma became fuel.
“That was the motivation to do well. So that I can be on my own and I don’t have to depend on my mother.”
The Path to the Bench
Jessica’s first career was in the hotel and restaurant industry. She worked at Caesars in Atlantic City, starting as entry-level management and getting promoted to assistant manager. She was doing the work of multiple people, working 55 hours a week, making $27,900 a year.
Her mother kept pushing her. What are you doing? Go back to school. Get a professional license.
One day, Jessica met with the vice president of legal at Caesars. The woman impressed her.
“I said I can do that job.”
So she went to John Marshall Law School in Chicago. She got pregnant in the middle of it. And something clicked.
“After I gave birth to my daughter, literally I was on the dean’s list. I did a JD and an LLM, a master’s in law, and I did it in three years. I was the first student to graduate with both degrees in just three years having a kid in the middle of it.”
While in law school, she finally applied for American citizenship. Taking that oath changed everything.
“When you take the oath with just different people from all walks of life, it’s inspiring. It means so much for those people who are standing there. I said, you know what, I want to give back to this country.”
She worked for the Illinois Department of Revenue as a special assistant attorney general. Did income tax litigation. Then volunteered for sales tax cases. Then the racing board, the liquor commission, the board of appeals. All at once. Because that’s who Jessica is.
When she got involved in bar association leadership and started evaluating judicial candidates, she realized something.
“I said to myself, I could do that. I could do better.”
Her mentor, Judge Sandra Otaka, the first Asian-American appointed and elected judge in Cook County, died during Jessica’s presidency of the Asian-American Bar Association. The Illinois Supreme Court quickly appointed a non-Asian replacement. The community wanted Jessica to condemn the decision publicly.
She refused.
“My position is that there’s no Asian seat. If you want to be considered, then put yourself on the list. We didn’t have anybody on the list.”
The immediate past president led the press conference instead. Jessica got canceled by her own community. But she walked the talk. She ran for judge herself. Against the Democratic Party machine. They told her to wait her turn.
“So I ran against the party and probably I shouldn’t have because you make so many enemies. But I ran and I won."
"I’m Dead”
The FBI called Jessica in her chambers in late 2016 or early 2017. They wanted to talk about two real estate transactions from 2007. Ten years earlier.
A friend who was an attorney told her not to meet with them.
“Jessica, you are not meeting with him. You and your husband are judges. Do you know what they would love to do just to get a name for themselves?”
Jessica pushed back. “I have nothing to hide.”
But she listened. She got an attorney. Her indictment came April 11, 2017, based on transactions that included a 2004 loan application, a 2005 refinance, and a $73,000 home equity line of credit her buyer took out in 2007.
The case hinged on whether certain lenders counted as “financial institutions” under federal law. At the time, mortgage companies were not FDIC-insured and did not meet the statutory definition. Congress changed the law two years later. But two years later doesn’t make it legal to apply that law retroactively.
When her attorney gave his opening statement, Jessica turned to her husband.
“I’m dead.”
His theory was that it was all a “mistake.” Jessica had never approved that approach.
“I didn’t even know what his theory was. I really didn’t know that was what he was going to say.”
By the third or fourth day, she was crying in the defense room.
“I want to represent myself. I don’t want you representing me anymore. You’re terrible. You don’t know what you’re doing. You’re not even objecting.”
Her husband talked her down. The trial continued. She and her attorney stopped speaking. She sat in silence while he, in her view, covered himself by saying “Let me check with my client” without actually checking with her.
“I was telling my husband, my clerk could have done a better job.”
The jury convicted her.
Volleyball Saved Her
Jessica got a year and a day in federal prison. She reported to Alderson, a camp in West Virginia.
When she arrived, prison officials gave her a choice: sign a waiver to be in general population, or be put in protective custody. They warned her that if other inmates found out she was a former judge, they might kill her.
“I’m like, no, no, they’re not. I’m not going to tell anybody.”
In her head: “I’m playing volleyball. If I’m in solitary confinement, I can’t play.”
Volleyball had been her first love in the Philippines. Now it became her salvation.
“It almost created this filter that everything’s okay. You’re in heaven. It really wasn’t, but it kept my mind occupied.”
She walked up the hill at Alderson and something strange happened.
“It was almost like God gave me this filter. It was this peace that just enveloped me. And I heard this voice saying, ‘You wanted to experience this. This is why you’re here.’”
A friend from her past life was already there and had supplies waiting. She introduced Jessica to the volleyball captain. Jessica made the team. Every team she was on won the championship.
“I was so competitive. Big deal? It was a big deal.”
The Fight Continues
Jessica served seven months and ten days. COVID hit while she was inside. Women were cutting each other during lockdowns. Camp life, supposedly for non-violent offenders, got brutal.
She came home in 2020 to uncertainty. Her marriage had nearly collapsed under the weight of the case. She didn’t know if she’d have a family to come back to.
She still has her family. And she’s still fighting her conviction.
Her case is now a pro se effort because she cannot afford an attorney. She’s filed a 2255 motion challenging her conviction based on what she believes is prosecutorial misconduct. She has emails she says prove the prosecutor knew testimony was false. She has what she considers a tampered exhibit.
The judge has not granted her an evidentiary hearing.
“My judge has never granted an evidentiary hearing to any defendant except for one case. And that case? The Department of Justice requested it.”
Jessica’s takeaway from everything she’s been through is blunt:
“Our criminal justice system is broken. There is an enormous and destructive indifference towards justice-impacted individuals. You don’t know until you go through it.”
She wants to unite the re-entry community into a political force. One-third of the country’s population is justice-impacted when you count family members.
“People are running for office, they take us for granted. But what they don’t know is we can actually affect elections. We have to remember our worth and we have to unite.”
And to anyone who won’t hire someone with a conviction:
“The way I look at this is that now that we’ve been through this, we’re really being very careful. The people you’re going to hire, they’re going to work hard because they’ve been through hell. And you can give them heaven and they will give you back heaven.”
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