The San Diego mayor who gambled $1 billion at casinos

Maureen O'Connor is garnering some unwelcome headlines for this mother of all betting sprees

"I never meant to hurt the city that I love." — San Diego Mayor Maureen O'Connor
(Image credit: Screen shot)

If you've ever woken up after a night of poker regretting that awful decision to buy back in for another $20, then you may have a microscopic notion of what Maureen O'Connor is going through. The former mayor of San Diego gambled a staggering $1 billion in casinos across the country over the course of a decade, a betting marathon that came to light when she was charged with laundering $2 million from a charity founded by her late husband. O'Connor made an appearance in court this week, where she admitted to having an out-of-control gambling addiction. According to The New York Times:

She walked unsteadily into court, leaning on a cane and appearing wobbly and distraught. She teared up as she told reporters, "Those of you who know me here would know that I never meant to hurt the city that I love."

Ms. O'Connor was not accused of taking money from the city, but the money in her husband's trust would probably have gone to local charities. "I always intended to pay it back and I still intend to pay it back," she said. [The New York Times]

All things considered, O'Connor didn't do too badly at video poker (her poison of choice), suffering a net loss of $13 million between 2000 and 2009. However, to keep fueling her gambling, she was forced to get rid of up to $50 million in assets — savings, belongings, and real estate — much of which had been bequeathed to her by her husband, Robert O. Peterson, who founded the popular Jack-in-the-Box burger chain. She partly blames a brain tumor, which she eventually had excised, for her bad decisions. "There are two Maureens — Maureen number one and Maureen number two," she said. "Maureen number two is the Maureen who did not know she had a tumor growing in her brain."

As part of a deal with prosecutors, O'Connor is expected to undergo treatment and pay back her husband's foundation.

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But that probably won't be the end of O'Connor's ordeal. As the Matt Damon's character says in the poker film Rounders:

In "Confessions of a Winning Poker Player," Jack King said, "Few players recall big pots they have won, strange as it seems, but every player can remember with remarkable accuracy the outstanding tough beats of his career." It seems true to me, cause walking in here, I can hardly remember how I built my bankroll, but I can't stop thinking of how I lost it.

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Ryu Spaeth

Ryu Spaeth is deputy editor at TheWeek.com. Follow him on Twitter.