The most significant portion of his career was with the Dodgers. A "bonus baby" who never really received a season-long chance to start in Cincinnati, Osteen was traded on Sept. 16, 1961, from Cincinnati to the Washington Senators for pitcher Dave Sisler. With the Senators, Osteen finally got a chance to start regularly in the majors, albeit with a consistently sub .500 team. In the winter of 1964, Osteen was traded from the Senators to the Dodgers in a 7-player deal, with four players (two of whom were Frank Howard and Pete Richert) going to the Senators. Osteen developed into one of the game\'s better starters in Los Angeles.\n', '

After two years with an earned run average under 3.00, Osteen was considered a top starter and a workhorse. In those two years, Osteen and the Dodgers reached two straight World Series, the last two Osteen would reach in his career. In the 1965 World Series, the Dodgers would beat the Minnesota Twins in seven games, and Osteen pitched brilliantly. He had a 0.64 ERA in the Series with a 1-1 record including a shutout, which came after teammates Don Drysdale and Sandy Koufax lost their respective games, the first two games of the Series. In the 1966 World Series, the Dodgers would lose to the Baltimore Orioles in four games. Osteen lost a 1-0 pitcher\'s duel with Wally Bunker in Game 3 despite giving up only three hits in seven innings; a home run by Paul Blair accounted for the game\'s only run. Osteen\'s final postseason statistics include a 0.86 ERA with seven strikeouts in 21 innings pitched.\n', '

In 1967, he reached his first All-Star game, going 17-17 with a 3.22 ERA in 288⅓ innings pitched. He also picked up 14 complete games on the year, with five shutouts. In 1968 Osteen was one of the game\'s consistent hard-luck losers. Despite a very respectable 3.08 ERA, he only won 12 of 30 decisions. The 12 victories would be his fewest in a season from 1964–1973; the 18 losses tied him with Ray Sadecki for the major league lead. In 1969, Osteen won 20 games for the first time and set a number of career highs:\n', '

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