Jessica Arong O’Brien was the epitome of the Filipino-American success story. Born in Cebu City in 1968, she immigrated to the US at age 16.

Despite facing challenges, including learning English, she excelled academically, earning a bachelor’s degree from Boston University and a highly specialized JD/LLM joint degree in tax law from John Marshall Law School.

Her career was a series of triumphs: she worked as an Assistant Attorney General for the Illinois Department of Revenue for 12 years and was a successful real estate agent.

Her personal life was equally stable, married to Brandon Allen O’Brien, an attorney who would later become a judge.

In 2008, Jessica’s remarkable achievement made history when she was selected to serve on the Illinois State Bar Association’s Board of Governors. In 2012, her ascent continued when she was elected as a Circuit Judge for Cook County, becoming the first Asian American woman to hold that position.

But the pedestal she stood upon concealed a staggering secret. On a Tuesday in April 2017, federal agents arrived at her Chicago home with an arrest warrant. The esteemed Judge O’Brien was arrested, shocking her family and the entire legal community.

The court records, which were later made public, revealed that her indictment was not related to her judicial role but to a complex mortgage fraud scheme orchestrated between 2004 and 2007, long before she became a judge.

The scheme, according to prosecutors, was driven by the O’Briens’ financial needs, leading Jessica to leverage her expertise as both an attorney and a licensed loan officer. She conspired with a loan originator and close friend, Maria Buco, to defraud multiple banks.

The core of the fraud involved repeatedly refinancing and securing loans on investment properties (on 54th and 46th Streets in Chicago). Jessica and Maria allegedly doctored loan application documents, inflating Jessica’s income and manipulating the value of the properties to secure massive refinancing amounts.

After securing the refinanced loans, Jessica used “straw buyers” whose names they paid to use for the mortgage. The buyers, who lacked the income to cover the monthly payments, quickly defaulted, leading the banks to foreclose on the properties.

The prosecution argued that between 2004 and 2007, Jessica successfully bilked banks out of over $1.4 million USD. The money was allegedly pocketed by Jessica and her accomplice.

Jessica’s defense team, led by a high-profile lawyer, argued that the discrepancies were mere “oversight” and clerical errors, denying any intentional deception. They insisted a woman of her intellect and standing would not jeopardize her career for such a crime.

However, the prosecution countered that both Jessica and Maria were sophisticated professionals who understood loan documentation intimately.

The repeated, systematic falsification of figures over several years made the claim of “oversight” impossible to believe.

The trial proceeded, and after a five-day hearing and eight hours of deliberation, the jury found Jessica O’Brien guilty on all counts of fraud.

On December 21, 2018, the judge sentenced her to one year and one day in federal prison, followed by two years of supervised probation.

Her accomplice, Maria Buco, received a lighter sentence in exchange for cooperating and testifying against O’Brien. Jessica served her sentence and was released in 2023.

The ordeal did not end with her release. The millions defrauded had to be repaid. As of 2024, she still reportedly owed over $650,000 USD in restitution to the victimized banks.

Prosecutors moved to seize her judicial pension, valued at over $116,000, to cover the debt, though the final ruling remains pending.

Furthermore, the Illinois Attorney Registration and Disciplinary Commission recommended stripping Jessica of her law license.

Despite her lawyer arguing she was a “model prisoner,” the board cited her lack of remorse and continued claims of innocence, concluding her behavior demonstrated a fundamental lack of fitness for the profession.

The rise of the trailblazing Filipina judge was tragically undone by the calculated greed of a mortgage fraud scheme.