Pride Fighting Championships
In 1997, Gracie signed up to a fight against Yoji Anjo's superior Nobuhiko Takada in the Pride 1 event. Before the Tokyo Dome's 47,860 spectators, Gracie defeated the inexperienced Takada, mounting him and locking an armbar in 4:47.
Now enjoying a growing popularity in Japan, according to Gracie he was proposed to fight Mario Sperry at Pride 3, but the process was stopped due to Carlson Gracie's disavowal. Pride management also offered him to take Royce Gracie's place in his cancelled match with Mark Kerr, but he refused, citing one month to be a too short time to prepare. Fighting Network Rings's chairman Akira Maeda also challenged Gracie and proposed a fight as his own retirement match, but it was rejected. Gracie only agreed to sign up to a rematch against Takada at Pride 4, stating: "I feel Takada is a warrior and deserves the chance to try and redeem himself."
In their rematch, Takada had improved and was able to wrestle Gracie to neutralize his groundwork advantage, but Gracie used a failed leglock attempt from the Japanese to sweep him and mount him. Nonetheless, Takada kept fighting under the jiu-jitsu master, dismounting him and threatening with a heel hook attempt, but Gracie, who was waiting until the end of the round to prevent Takada from capitalizing should he miss his opportunity, applied an armbar and submitted him again.
In May 2000, after Takada understudy Kazushi Sakuraba defeated Royler Gracie in the Pride 8 event, he took the mic and challenged Gracie, who was in the Gracie corner, but nothing came of it. Gracie preferred to face Pancrase's retired ace Masakatsu Funaki at Colosseum event. The event almost got cancelled, as Gracie demanded special rules which banned headbutts, elbow strikes, and strikes to the head both standing or on the ground, but an agreement was reached when the Pancrase management conceded to ban headbutts and elbows.
At the event, held at the Tokyo Dome and broadcast to 30 million TV Tokyo viewers, Gracie and Funaki started the fight clinching to the corner. Masakatsu appeared to have secured a guillotine choke, but the hold was loose and Gracie managed to go to the mat, although receiving a hammerfist that marked his face. They traded kicks to no effect, until some well timed upkicks from Gracie blew out Funaki's gravely injured right knee. They clinched again, but the Japanese's injury rendered him unable to wrestle Gracie correctly, and he was taken down by the Brazilian, who promptly mounted him. Masakatsu looked stunned while Gracie bloodied his face with ground and pound, and finally Gracie forced his way into a rear naked choke. During the post-match interview, Gracie claimed that the hammerfist delivered by Funaki made him lose his eyesight for a few moments.
After the Colosseum event, Gracie expressed interest in fighting judo medalist Naoya Ogawa, who was signed up for the next Colosseum event. He was also proposed by Pride management to fight Kazushi Sakuraba, who had already defeated Royce Gracie as well, but Gracie refused saying that Sakuraba "didn't have the spirit of a warrior". Gracie further said he didn't want to fight a wrestler who was so much smaller than him. Thus, New Japan Pro-Wrestling invited him to face Shinya Hashimoto, Manabu Nakanishi or Kazuyuki Fujita, but they were refused. The fight against Ogawa was set to the next year, with Naoya vacating his NWA World Heavyweight Championship to focus on training for the bout.
However, tragedy struck when Gracie's son Rockson was found dead in January 2001. Affected by the loss, Gracie contemplated retirement, and the fight against Ogawa fell off after some negotiations. Months later, he stated he was willing to fight again and evaluating propositions, but nothing came from it. When the matchup with Sakuraba was brought up again, Gracie expressed disinterest.
