Born in Bahia, Brazil and famed for his wars against the gracie family, specially Hélio Gracie, this fighter had a humble and deprived childhood. He first started at the Gracie Academy in the 1930´s as a cleaner, training with the rest of the team on occasion. Noticing his athletic abilities from the start, Hélio Gracie – the head teacher of the academy, started introducing him into the more advanced students classes, making him at one point the co-instructor of the classes. He also fought in “Vale Tudo” (no-holds-barred) fights under the Gracie Jiu-Jitsu banner.
This “honey moon” environment between Waldemar Santana and Helio, which lasted five years, came to an end when Waldemar after his daily chores at the Jiu Jitsu academy, forgot a tab on, on a weekend which left the academy soaked when The students arrived on the following Monday. Helio did not measure his tone when reprimanding Waldemar and the pair had a heated exchange of words ending in Helio dismissing Mr Santana from his post at the Jiu Jitsu academy.
Waldemar Santana then joined another Jiu Jitsu Academy, from another dissident of the Gracie Jiu Jitsu Academy, Mr Haroldo Brito.
After a period of hard training at his new home, Waldemar came out and challenged his former mentor, Helio Gracie promptly agreed and the fight was arranged. Waldemar Santana was 26 years of age at the time of the fight, contrasting the 42 years of Helio Gracie and the fight made history for lasting almost 3 hours. It also made history as the underdog Waldemar Santana defeated the all mighty Helio Gracie with a soccer kick to the head.
After the Helio Gracie fight, Waldemar Santana was challenged by Helio’s older brother and leader of the Gracie clan Carlos Gracie to fight his son Carlson Gracie. Carlos even promissed to hand out a huge purse money if his son Carlson didn’t finish him. Unfortunately for Master Carlos Gracie’s pocket, Carlson Gracie didn’t manage to get the tap out he so eagerly fought for and the fight was declared a draw as no point system was in place.
They arranged a second fight to remove all doubt between whose Jiu Jitsu was better, Carlson Gracie’s or Waldemar Santana’s. The fight was arranged for the 21st of July 1956 in Maracanãzinho, a famous Rio de Janeiro venue, and it sold out every one of it’s 40,000 tickets. This second fight went rather differently from their previous encounter and Carlson beat his opponent repeatedly until Waldemar Santana´s corner finally threw in the towel to the ring.
Waldemar Santana pursued his fighting career elsewhere, but never did he fight again in such a high profile fight in the MMA circuit of the 1950’s. Even when the pair fought again a couple of years later, the glamour and hype had passed away and the 3rd fight was a lacklustre draw once again.