Maureen O’Connor was the first female mayor of San Diego, California, from 1986 to 1992. When her husband, Robert O. Paterson, founder of the fast-food chain Jack in the Box, passed away in 1994, she inherited his entire $50 million fortune since the couple had no children.
But O’Conner still ended up in debt. Specifically, it was gambling debt, but her addiction wasn’t something she could control.
Doctors determined that the grief brought on by her husband’s death and a brain tumor had changed her personality, allowing her to get hooked on video poker.
It turns out you can win and lose quite a bit of money by playing poker online. O’Conner’s “grief gambling” did bring her over $1 billion (yes, with a B) worth of good luck and winnings over the course of a decade. However, she lost so much that she wiped out her winnings AND her inherited fortune.
In the end, she was worth negative $13 million.
It was more than she could pay off, so O’Conner turned to money laundering and was convicted of the crime in 2013 after taking money from her late husband’s non-profit to cover the gambling debts.
She was given a deferred sentence and served no jail time under the health circumstances, but she was completely broke after paying court costs and restitution.
If you do the math, she would have needed to wager roughly $300,000 a day, seven days a week, to lose as much money as she did in such as short period of time. And yet she’s far from the biggest loser when it comes to gambling.
According to the New York Times in 2013, “Terry Watanabe, a businessman, lost more than $205 million in Las Vegas, including more than $120 million in 2007 alone. The British media mogul Robert Maxwell once lost £1.5 million, about $2.3 million, in less than three minutes at a London casino.” – WTF fun facts