It is safe to say that Maureen O’Connor, former San Diego mayor and widow of Jack-in-the-Box founder Robert O. Peterson, was probably more comfortable sitting in front of a casino video-poker machine than a judge in federal court.

O’Connor pleaded guilty to a money laundering charge Thursday after agreeing to a plea deal that lets her try to pay back $2.1 million she took from Peterson’s charitable foundation to cover gambling debts. She has two years to make good on her promise or prosecution could resume.

But according to the Los Angeles Times, papers filed by the prosecutor indicate O’Connor’s declining health “renders it highly improbable—if not impossible—that she could be brought to trial.”

O’Connor, who walks with a cane, is nearly destitute, according to her lawyer. Peterson, 30 years her senior, died in 1994. She reportedly lost $13 million gambling between 2000 and 2009, while placing wagers worth $1 billion. O’Connor’s attorney said she would play video-poker for hours at the Barona Resort & Casino near San Diego. But she was also a regular in Las Vegas, where casinos would send a jet for her.

O’Connor admitted taking money from the R.P. Foundation in 2008 and 2009 while she was one of its trustees. The nonprofit organization contributed money to the City of Hope, San Diego Hospice and the Alzheimer’s Association, but a federal official said it went broke and closed in 2009. A 2011 federal tax filing obtained by the San Diego Reader listed the foundation’s total assets as $2.1 million in “receivables due from officers, directors, trustees and other disqualified people.”

At a press conference after the court appearance yesterday, O’Connor spoke about her difficulties, and about a brain tumor diagnosed in 2011. “There are two Maureens—Maureen No. 1 and Maureen No. 2,” she said. “Maureen No. 2 is the Maureen who did not know she had a tumor growing in her brain.”

The two-time mayor flourished politically in San Diego despite being a Democrat in a decidedly Republican city. She was on the city council by age 25, She was the city’s first woman mayor (1986-1992) and the last Democrat elected to the post until last November.   

–Ken Broder

To Learn More:

O’Connor Had $1 Billion Gambling Habit (by Greg Moran, U-T San Diego)

Foundation at Heart of O'Connor Scandal Was Big Donor to San Diego Police; John Burton Foundation (by Matt Potter, San Diego Reader)

Ex-San Diego Mayor's Gambling Wagers Top $1B (by Elliot Spagat, Associated Press)

San Diego Ex-Mayor Used Charity Funds to Cover Gambling Debts (by Tony Perry, Los Angeles Times)