Hélio Gracie
He is famous for fighting his former master Hélio Gracie in 1955. Valdemar fought for the original Gracie Academy for many years but had a falling out with Hélio. Gracie and Santana decided to settle their differences in a Vale Tudo (no holds barred) match. After more than three hours and forty minutes of combat, Santana knocked out Gracie with a soccer kick to the head.