Following a mid-season trade to Oakland in 1989, Henderson reasserted himself as one of the game's greatest players, with a memorable half-season in which his 52 steals and 72 runs scored led the A's into the postseason; his 126 walks for the year were the most for any AL hitter since 1970. With a record eight steals in five games, he was named MVP of the American League Championship Series; he hit .400 while scoring eight runs and delivering two home runs, five runs batted in (RBI), seven walks and a 1.000 slugging percentage. Leading the A's to a four-game sweep over the San Francisco Giants and the franchise's first World Series title since 1974, Henderson hit .474 with an .895 slugging average (including two triples and a homer), while stealing three more bases. On August 22, 1989, he became Nolan Ryan's 5,000th strikeout victim, but Henderson took an odd delight in the occurrence, saying, "If you haven't been struck out by Nolan Ryan, you're nobody."  A year later, Henderson finished second in the league in batting average with a mark of .325, losing out to the Kansas City Royals' George Brett on the final day of the season. Henderson had a remarkably consistent season, with his batting average falling below .320 for only one game, the third of the year. Reaching safely by a hit or a walk in 125 of his 136 games, he led the league in runs (119), stolen bases (65), on-base percentage (.439) and OPS (1.016) was 2nd in slugging % (.577), 4th in walks (97) and extra base hits (66), 6th in home runs (28) and total bases (282) and had 61 RBI and Henderson won the AL's MVP award and helped Oakland to another pennant. He again performed well in the World Series (.333 batting, .667 slugging, a home run and three steals in four games), but the A's were swept by the underdog Cincinnati Reds.  On May 1, 1991, Henderson broke one of baseball's most noted records when he stole the 939th base of his career, one more than Lou Brock's total compiled from 1962 to 1979, mainly with the St. Louis Cardinals.  In 1993, Henderson was having another outstanding season when he was traded to the Toronto Blue Jays at the trade deadline. In 90 games with Oakland, he was batting .327 (2nd in AL) with 17 home runs and 47 RBIs. He also had scored 77 runs, stolen 31 bases, drew 85 walks, had a .469 on-base percentage and was slugging .553.

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