She crossed $1B through the casinos and still ended up bankrupt after stealing $2M from her charity 💀

Maureen O'Connor was the first female mayor of San Diego, coming from a large working-class family, built a strong reputation, even pretending to be homeless to understand the streets
Later married the founder of Jack in the Box, inherited a huge fortune after his death
From there, things took a turn for the worse, became addicted to video poker and started gambling nonstop, over time betting more than a billion dollars in casinos
Even with big wins, she ended up losing $13 million, sold properties, drained savings, took out loans, by 2008 she was bankrupt
Then things got worse, took about $2.1 million from her private charity to keep gambling, describing it as loans, the charity collapsed because of it
She was federally charged in 2013, but avoided jail through an agreement: repay the money, fix taxes, go to addiction treatment
The case was dropped in 2015 but she lost her money, her reputation, and everything