From Judge to Prison: Jessica O'Brien's Fall and Rise

From the Philippines to the Bench

Jessica O’Brien came to America at 16, speaking English her teacher said would never get her anywhere. “You’re going to America. You have a horrible English. You will never succeed in America. You’ll be nobody,” her teacher told her back in the Philippines. Those words stuck, but they didn’t stop her. Jessica became the first Filipino American judge elected in Cook County, Illinois.

Her path wasn’t straight. Jessica’s mother was a young medical student who came to the U.S. to practice in an underserved community in the Bronx. Jessica stayed behind with her father until high school, when she finally made the move that would change everything. “I knew that I wasn’t going anywhere if I stayed in the Philippines,” Jessica told me. “I sucked it up and I came to America.”

The transition hit hard. Sexual abuse she kept to herself. A mother who didn’t believe her when she tried to speak up. But volleyball became her anchor, and college at Boston University opened her world. She studied abroad in Europe, found her confidence, and started building the life she wanted.

Finding Law Through Customer Service

Jessica’s first career was in hotels and casinos. She worked at Caesars, climbing from entry level to divisional food and beverage trainer, managing thousands of employees. The work was demanding but unfulfilling. “I was making 27,900,” she remembered. “I mean, you think about it. Here I am doing multiple jobs, working literally 50, 55 hours.”

It was meeting the vice president of legal at the casino that sparked something. “I would listen to her and I’d said, I can do that job,” Jessica said. Her mother, a doctor, kept pushing her to get a professional license and do something meaningful with her education.

Law school changed everything. Jessica fell in love with the law and applied for American citizenship during her first or second year. Taking the oath with people from all walks of life gave her a sense of purpose she’d been missing. “I want to give back to this country,” she decided. “And I know that sounds cliche, but it’s this pride, you know, you’re taking on a different citizenship.”

The Hyperactive Attorney

Jessica graduated and landed at the Illinois Department of Revenue as a special assistant attorney general. Her self-described “hyperactive” nature kicked in immediately. Hired to do income tax litigation, she volunteered for sales tax too. When Governor Blagojevich merged agencies and they lost attorneys, Jessica volunteered for three more departments. Racing board, liquor commission, board of appeals. She was covering five different agencies.

“I was so hyper,” she explained. “I was bored with just doing income tax. I volunteered to the sales department. I’m like, I can do that too.”

This period taught her litigation the hard way. At her previous law firm, she’d frozen in court when sent to ask for a simple extension. The judge never looked at her, so she said nothing. “I figured you don’t speak when you’re not spoken to,” she remembered. At Revenue, she got thrown into trials immediately and learned to fight.

But Jessica couldn’t sit still. During maternity leave, she studied for her broker’s license and started a small real estate company. The hyperactive streak that served her well as an attorney would later become part of the prosecution’s case against her.

Running Against the Machine

Becoming a judge wasn’t planned either. Jessica got involved in bar organizations, eventually becoming president of the Asian American Bar Association. She served on judicial evaluation committees, interviewing candidates for judge positions. “It was during that time when we were interviewing all these candidates that I said to myself, I could do that,” she told me.

When her mentor, Judge Sandra Otaka, died and the Illinois Supreme Court quickly appointed a non-Asian replacement, the Asian American community wanted Jessica to condemn the decision. She refused. “There’s no seat. There’s no Asian seat,” she said. “A person should be the person that gets on the merits.”

So she decided to walk the talk and run herself. The first attempt failed when she couldn’t gather enough signatures. Two years later, she tried again. The Democratic Party was still angry about her previous run. “We’re not endorsing you,” they told her. “You ran against us, you know, so you got to wait your turn.”

Jessica ran against the machine anyway. And won.

The Judge Who Viewed It as Customer Service

Wearing the robe felt different than Jessica expected. “I really viewed the bench as the judiciary’s customer service,” she said. “You’re serving the people. And again, I’m coming from the hospitality industry. I figured the judge is the manager of the customer service in my courtroom.”

She remembered that first court appearance where the judge never looked at her, and she made sure to see everyone who came before her bench. The formality felt unnecessary sometimes. “I wasn’t comfortable with people when they people get up because it’s just like so unnecessary,” she said. “I’m just here to settle. I’m a servant. I’m really working for all of you.”

Jessica served as judge from 2012 to 2018, bringing that customer service mindset to criminal and civil cases. She thought she’d found her calling, the place where all her experiences would make sense together. But life had other plans.

From Volleyball Courts to Prison Yards

Jessica’s story doesn’t end with success on the bench. Federal charges brought her world crashing down, and she found herself in the system she’d once presided over. She fought the charges, going to trial when 97% of defendants plea out. She lost.

In prison, volleyball saved her again. The sport that had been her first love in the Philippines became her lifeline behind bars. “Volleyball saved me in prison,” she said. “It almost created this filter that everything’s okay. You’re in heaven. It really wasn’t. But it kept my mind occupied.”

Jessica served a year and a day in federal prison. She’s still fighting to vacate her conviction, still believing in the system even after it crushed her dreams. Her experience gives her a perspective on criminal justice reform that few judges ever get. She lived both sides of the courtroom, and that lived experience drives her passion for making things better.

The teacher who said she’d be nobody in America got it wrong. Jessica became somebody, lost it all, and is becoming somebody again. Her story isn’t finished.