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1970–71 NBA season: conference finals loss and challenge to Muhammad Ali

In the 1970–71 NBA season, the Lakers signed Gail Goodrich, who had returned from the Suns. Chamberlain averaged 20.7 points, 18.2 rebounds, and 4.3 assists; he once again led the NBA in rebounding and the Lakers won the Pacific Division title. When Hall-of-Fame Detroit Pistons center Bob Lanier, who was 6 ft 11 in (2.11 m) and 250 lb (110 kg) as a rookie, was asked about the most memorable moment of his career, Lanier answered: "When Wilt Chamberlain lifted me up and moved me like a coffee cup so he could get a favorable position".

After losing Baylor to an Achilles tendon rupture that effectively ended his career, and especially after losing West after a knee injury, the Lakers were seen as underdogs in the playoffs against the Milwaukee Bucks of Alcindor—freshly crowned MVP—and the veteran Hall-of-Fame guard Robertson, whom they played in the Western Conference Finals. After winning the regular season with 66 wins, the Bucks were seen as favorites against the depleted Lakers; many pundits were looking forward to the matchup between the 34-year-old Chamberlain and the 24-year-old Alcindor. In Game 1, Alcindor outscored Chamberlain 32–22 and the Bucks won 106–85. In Game 2, the Bucks won again despite Chamberlain scoring 26 points—four more than his Milwaukee counterpart. Prior to Game 3, the Lakers' situation worsened when West's stand-in Erickson underwent an appendectomy and was out for the season. With rookie Jim McMillian easing the scoring pressure, Chamberlain scored 24 points and grabbed 24 rebounds in a 118–107 victory but the Bucks defeated the Lakers 117–94 in Game 4 to take a 3–1 series lead. Milwaukee ended the series at home with a 116–98 victory in Game 5. Although Chamberlain lost, he was lauded for holding his own against MVP Alcindor, who was 10 years younger and healthy.

After the playoffs, Chamberlain challenged heavyweight boxing legend Muhammad Ali to a fight. Chamberlain trained with Cus d'Amato for the 15-round bout, set to take place on July 26, 1971, in the Houston Astrodome. Ali refused to be intimidated, issuing his typical public boasts, this time of "Timber!" and "The tree will fall!". In 1965, Chamberlain consulted his father, who had seen Ali fight, and advised Chamberlain against it. Cooke offered Chamberlain a record-setting contract on the condition he agreed to give up what Cooke termed "this boxing foolishness". Chamberlain ultimately used a contractual escape; Joe Frazier gave Ali his first professional loss, enabling Chamberlain to legally withdraw from the bout. Retired NFL player Jim Brown, who acted as Chamberlain's manager since 1967, got Ali's manager Jabir Herbert Muhammad to mutually withdraw from the match set to take place at Madison Square Garden.