In the 1969 NBA Playoffs, the 55-win Lakers defeated the Atlanta Hawks and the San Francisco Warriors, setting up the sixth finals series versus Boston in eight years. Before Game 1, West privately complained to Bill Russell of exhaustion, but then the Lakers guard scored 53 points on Boston in a close two-point win. L.A. also took Game 2, with West scoring 41 points. In Game 3, Russell opted to double-team West, and the guard's exhaustion began to show: West twice asked to be subbed for longer periods, and both times the Lakers fell back by double digits and finally lost by six points. Game 4 saw Celtics guard Sam Jones hit an off-balance buzzer beater to tie the series, but in Game 5, the Lakers struck back and won by 13 points; however, they suffered a major blow when West – who scored 39 points and by far led all players in scoring during the entire series – lunged for a meaningless late-game ball and seriously pulled his hamstring: it was immediately visible that the injury would not heal until the end of the series. A limping West scored 26 points in Game 6, but the Celtics won 99–90 with a strong Bill Russell, who held Chamberlain to only eight points in the entire game. In Game 7, Lakers owner Jack Kent Cooke had put up thousands of balloons in the rafters of the Forum in Los Angeles. This display of arrogance motivated the Celtics and angered West. The Lakers trailed the entire game and were behind 91-76 after 3 quarters, but powered by a limping West, the Lakers closed the gap to 103–102 with two minutes to go and had the ball. But West committed costly turnovers and L.A. lost the game 108–106 despite a triple-double of 42 points, 13 rebounds and 12 assists from West, who became the only recipient of the NBA Finals Most Valuable Player Award from the losing team. After the loss West was seen as the ultimate tragic hero: after the game, Bill Russell held his hand, and John Havlicek said: "I love you, Jerry".
West was an all-around combo guard who could take the playmaking roles of a point guard and score like a shooting guard, while being equally strong on offense and defense. He had a jump shot with a release the NBA lauded as "lightning quick", and was known for making baskets late in the game, earning him the nickname "Mr. Clutch". Having played forward early in his career, West was also a capable rebounder, and gifted with long arms, quick hands, and strong defensive instincts, West was also once described as one of the best ballhawks, man-to-man defenders and shot blockers among NBA guards: when the All-Defensive Teams were introduced in 1969, West made every one of them until his career ended in 1974. "He stole more than anybody, although they didn't keep records on it then", said Sharman. However, contemporaries were most impressed by West's work ethic, obsessively practicing and shooting and rarely being satisfied with himself.