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After brief call-ups during the two seasons before, Kelly won the Yankees' centerfield job in 1989 after incumbent Claudell Washington wasn't re-signed. He responded with enthusiasm, hitting a surprising .302 and swiping 35 bags, and stuck with the Yanks for three more years. In 1991 he became the fifth 20-20 Yankee, and the following season he was chosen to the All-Star team.
But despite being heralded as the Yankee star of the future, Kelly's homers and walks actually decreased in 1992 while his strikeout total increased. Additionally, questions about his motivation bubbled up in the Yankee front office and New York tabloids, and Kelly began to yield his spot in the order to a young centerfielder named Bernie Williams.
In November 1992, he was traded to the Cincinnati Reds for a minor-league first baseman and Paul O'Neill, who would go on to fame, fortune, and four World Series rings as the Bombers' right-fielder. Kelly wouldn't get any rings, but he would get a name change the following spring. When he got off to a bad start in 1993, he asked the scoreboard operator and program editor at Riverfront Stadium to change his name to "Bobby." His first time up with the new moniker in place, Kelly hit a triple and subsequently went on a 14-game hitting streak. The nickname stayed until November.
Kelly separated his shoulder in June 1993 and was out for the remainder of the season. After his return to the majors the following season, he would find himself traded three times over a year and a half. Though he hit .302 through the first 47 games for the Redlegs, Cincy shipped him to the Atlanta Braves for Deion Sanders in May 1994. In April 1995, he was traded with Tony Tarasco and Esteban Yan to the Montreal Expos for Marquis Grissom, then again to the Los Angeles Dodgers for Henry Rodriguez and Jeff Treadway in May 1995. The subsequent years saw Kelly shipped and signed with the Minnesota Twins, Seattle Mariners, Texas Rangers, and once again with the Yanks.
Though he rarely got a chance to play every day, when he did he was as potent as his teams could have hoped. Like Stan Javier, Kelly was considered one of the most valuable fourth outfielders in the majors. Clubs entering postseason play could always find use for an fielder who excelled defensively at all three outfield positions, carried a 74% stolen base success rate, and had a .290 career batting average. His consistency off the bench against southpaw pitching was prized as well: from 1995 to 2000, he batted .344 against them for his seven different teams.