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Reputation as a loser

Although Chamberlain accumulated some of the most-impressive statistics in the history of professional sports, he was often called selfish and a loser because he won only two NBA championships and lost seven out of eight playoff series against Bill Russell's Celtics teams. Frank Deford of ESPN said Chamberlain was caught in a no-win situation: "If you win, everybody says, 'Well, look at him, he's that big'. If you lose, everybody says, 'How could he lose, a guy that size?' " Quoting coach Alex Hannum's explanation of his situation, Chamberlain often said: "Nobody roots for Goliath".

Rick Barry wrote:

I'll say what most players feel, which is that Wilt is a loser... He is terrible in big games. He knows he is going to lose and be blamed for the loss, so he dreads it, and you can see it in his eyes; and anyone who has ever played with him will agree with me, regardless of whether they would admit it publicly... When it comes down to the closing minutes of a tough game, an important game, he doesn't want the ball, he doesn't want any part of the pressure. It is at these times that greatness is determined and Wilt doesn't have it. There is no way you can compare him to a pro like a Bill Russell or a Jerry West... these are clutch competitors.

Chamberlain's main weakness was his poor free-throw shooting, a.511 career average, the third-lowest in NBA history, with a low of.380 over the 1967–68 season. Chamberlain later said he was a "psycho case" in this matter. Much like later center Shaquille O'Neal, Chamberlain would be intentionally fouled and was a target of criticism because of it. Many suggestions were offered; he shot them underhanded, one-handed, two-handed, from the side of the circle, from well behind the line, and banked it in. Coach Hannum once suggested Chamberlain shoot his fadeaway jumper as a free throw but Chamberlain feared drawing more attention to his main failing.

Despite his foul-line problems, Chamberlain set the NBA record, which was later equaled by Adrian Dantley, for the most free throws made (28) using the underhand technique in a regular-season game in his 1962 100-point game. Chamberlain later said he was too embarrassed by the underhand technique to continue using it, although it consistently gave him better results. Chamberlain stated he intentionally missed free throws so a teammate could get the rebound and score two points instead of one.