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Henderson, was born in Chicago, but grew up in the city of Oakland, California and became friends with Oakland Athletics owner Charles O. Finley as a boy. Henderson, blessed with speed and explosiveness, was eventually drafted by Oakland in the 1976 Major League Baseball draft and worked his way through the minor leagues in just three seasons. He made his big league debut with Oakland on June 24, 1979.
Henderson batted .274 with 33 stolen bases in little more than half a season and was a strong Rookie of the Year candidate in 1979. Finley hired legendary manager Billy Martin in 1980, and his "Billy-Ball" propelled Rickey into stardom, when he became one of the few players to ever steal 100 bases in a season. He was an MVP candidate a year later, when he hit .319, fourth in the American League, and again led the league in steals with 56 in a season shortened by a players' strike. Finishing second to Rollie Fingers, Henderson's flashy fielding that season also earned him his only gold glove.
Henderson set a modern major league record, still standing, with 130 stolen bases in 1982. He also continued to develop as a hitter, and even began to hit for some power. In 1985, he was traded to the New York Yankees, and that year he scored 146 runs in just 142 games, with 24 home runs and 80 steals. He later hit as many as 28 homers in a single season.
He had an off-season, by his standards, in 1989, caused somewhat by restless Yankee fans and media dogging him, but bounced back during the postseason after being traded back to Oakland mid-year. He was MVP of the American League Championship Series and led the A's to their first World Series title since 1974.
A year later, he finished second in the league in batting average with a mark of .325, losing out to George Brett on the final day of the season. Nevertheless, with 119 runs scored, 28 homers, 61 RBI and 65 stolen bases, he won the MVP award and helped Oakland to another pennant.
On May 1, 1991, Henderson broke one of baseball's most famous records when he stole the 939th base of his career, one more than Lou Brock. However, Henderson's achievement was somewhat overshadowed because Nolan Ryan, at age 44, set a record that same night by throwing his seventh no-hitter. It was also overrshadowed by his famous speech afterwards where he famously proclaimed "...today, I am the greatest of all time." Two years earlier, Ryan had also achieved glory at Henderson's expense by making him his 5,000th strikeout victim. As it now stands, however, Henderson has almost one-half more stolen bases than Brock, a record that may prove unbreakable in the near future.
In his prime, Henderson had a virtual monopoly on the stolen base title in the American League. Between 1980 and 1991, he led the league in SB's every season except 1987, when an injury caused him to lose the title to Seattle Mariners second baseman Harold Reynolds.
Henderson went on to have many more good seasons, and earned a second ring with the Toronto Blue Jays, who acquired him in midseason from Oakland, in 1993. He returned to Oakland after the season for two years, and made a 3rd return to Oakland in 1998, where he led the American League in stolen bases for a record 12th time at age 39. During the 2001 season, as a member of the San Diego Padres, Henderson broke 2 major league records and reached a career milestone. He broke Babe Ruth's all-time record for walks, Ty Cobb's all-time record for runs (doing so with a home run), and on the final day of the season, during Padre legend Tony Gwynn's last major league game, Rickey garnered his 3,000th career hit.
Rickey played with the Boston Red Sox in 2002, where he became the oldest player to play centerfield in major league history. It was the 8th organization he played for in his career, having also played with the Anaheim Angels, New York Mets, and Seattle Mariners in his career.
He started 2003 playing in the independent Atlantic League with the Newark Bears, hoping for a chance with another major league organziation. Rickey got that chance (after much big media attention in the meantime) when the Los Angeles Dodgers signed him to their roster over the All-Star break.
So far, Rickey ranks 4th all-time in games played (3,051), 10th in at-bats (10,889), tied for 21st in hits (3,041) and first in runs scored (2,288), walks (2,179), and stolen bases (1,403).
Henderson is very unusual in that he throws left-handed and bats right-handed. Many right-handed throwers bat left-handed, but the opposite is extremely rare, especially among non-pitchers.