Lottery

I've only had one sim win while I was playing him. Which was fine, he lived in a shack with only the bare essentials :D

I've seen Judith Ward, Bella Goth, Catarina Lynx, Mayor Whiskers (indeed won at least twice, I adopted him one of those times), and I believe also one of the Behr sisters. The rest have been random townies, who then get a makeover and a nice house.