Henderson perfected the art of stealing bases at a time when fans tended to champion power hitters. Speed demon Lou Brock, Henderson's predecessor in record-setting stolen bases, was on the verge of retirement when Henderson's career was beginning. Henderson took it upon himself to keep up the tradition, and the Chicago-born player was soon on the road to eclipsing Brock's career record.
In 1984 Henderson was traded to the New York Yankees, where he was reunited with former A's manager Billy Martin. In one of his best seasons to date, he hit twenty-four home runs and ended with a .314 batting average. Although he did not top his personal best in 1984, he led the league that year in stolen bases (80). His value on the Yankees was second only to champion slugger Don Mattingly.
Unusual for having a left-handed throw and a right-handed batting stance, Henderson excelled as both an outfielder and a hitter. In 1986 he hit a career high of twenty-eight home runs; he also scored 146 runs—more than any other player since Ted Williams. He averaged more than one run per game, a percentage comparable to that of legendary Yankee Lou Gehrig. As an outfielder he proved himself to be versatile, moving from left to center field in 1985 (he later returned to his preferred left field). For his deft-looking catches, Henderson earned the nickname "Style Dog." As a Yankee he continued to prove his base-stealing prowess, logging ninety-three steals in 1988.
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