When was the last time a Gracie tapped?
Kazushi Sakuraba .vs. Royce Gracie. PRIDE
After a 90 minute battle of punishing leg kicks, Royce's brother threw in the towel. Gracie could no longer stand and suffered a broken femur from accumulated damage. Sakuraba would go on to defeat other members of the Gracie family including Renzo Gracie and Ryan Gracie earning him the nickname "Gracie Hunter."
From dictionary.com
Throw in the towel definition. To quit in defeat. The phrase comes from boxing, in which a fighter indicates surrender by throwing a towel into the ring.
Gracie returned to PRIDE in 2002 to fight Japanese gold-medalist judoka Hidehiko Yoshida in a Judo vs. Brazilian Jiu-Jitsu limited rules MMA match. Gracie lost that match when the referee stopped the match after Yoshida had sunk in a deep gi-choke. Almost immediately, he contested the loss stating that he was fully conscious when the match was stopped. Later backstage, the Gracies demanded it be turned into a no contest, and an immediate rematch be booked (with different rules for the next time). If not, the Gracie family would pull themselves from PRIDE FC, and never fight for them again. PRIDE, wanting to keep the Gracie family with them, accepted their demands.