Ex-Mayor’s $1 Billion Gambling Woes Stun San Diego

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News of O’Connor’s gambling troubles and financial ruin elicited sympathy in her hometown. Magistrate Judge David Bartick told her that she left “a very strong legacy in the city of San Diego.”

The U.S. attorney’s office said O’Connor’s medical condition influenced the decision to strike a deal, saying it may have been impossible to bring the case to trial. The tumor was removed but doctors submitted letters detailing significant ailments.

“Maureen O’Connor was a selfless public official who contributed much to the well-being of San Diego,” said U.S. Attorney Laura Duffy. “However, no figure, regardless of how much good they’ve done or how much they’ve given to charity, can escape criminal liability with impunity.”

O’Connor, the eighth of 13 children whose father was a boxer and nightclub owner and mother was a registered nurse, was elected to the City Council three years after graduating from San Diego State University. She was mayor from 1986 to 1992, San Diego’s only Democratic leader over a four-decade span. She promoted community policing, championed the arts and oversaw completion of a downtown convention center.

O’Connor began gambling around 2001 as she struggled with pain and loneliness from the death of her husband from leukemia in 1994 and the passing of several close friends, said Iredale, who called it “grief gambling” in a court filing. Within four years, she was betting heavily.

O’Connor acknowledged taking $2.1 million from the R.P. Foundation between September 2008 and March 2009 to pay gambling debts, wager more and cover living costs. She was one of three trustees of the foundation, a nonprofit organization that supported the Alzheimer’s Association, City of Hope, San Diego Hospice and other charities.

Her annual gambling winnings peaked at more than $200 million, said Phillip Halpern, an assistant U.S. attorney. Prosecutors said they didn’t know exactly how much she lost but that she also borrowed money from friends and sold property to gamble.

O’Connor sold a home in tony La Jolla for $2.5 million in 2010 that is down the street from former Republican presidential nominee Mitt Romney.

She also sold the Heritage House Hotel in the Northern California coastal town of Mendocino for $7.5 million in 2005 to investors who defaulted, Iredale said. She sued and plans to turn over any damages to repay the foundation.

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