12. Kenny Anderson
No. of kids / No. of baby mamas: 7 / 5
Kenny Anderson had a decent NBA career which spanned 14 seasons with teams like the Clippers, Nets, Celtics, Hawks, Hornets, Blazers, and Pacers. After making about $63 million during his playing days, Anderson still managed to go broke and successfully file for bankruptcy in '05. Over $40K in expenses and child support payments earned him a spot on this list. Life of a Baller 101: $12 for a box of rubbers >>> thousands per month in child support payments.