9. Evelyn Adams ($5.3 million in 1985 and 1986)
Evelyn Adams was living an unbelievable life. She won the lottery not just once but twice! If you look up the word “lucky” in a dictionary, her name would be all over it.
Evelyn’s first win was in 1985, and the second one was a year later. In total, she got $5.3 million out of the New Jersey lottery. She got too cocky with her luck and spent them all on shopping sprees and gambling in Atlantic City.
She was then married to her fiancé, Ed Baseshore, and goes by the name Evelyn Baseshore. Evelyn lost it all and has been living in a trailer park.
In 2012, she told the New York Post that she is still playing the lottery. But today, she cannot be contacted.