The most significant portion of Osteen's career was spent with the Dodgers. A "Bonus Baby" who never really received a season-long chance to start in Cincinnati, he 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 big leagues, albeit with a consistently sub-.500 team. After posting a winning record in 1964, he was in much demand that winter. On December 4, 1964, Osteen was traded by the Senators to the Dodgers in a 7-player deal, with five players going to the Senators. Osteen developed into one of the game's better starters in Los Angeles. After two years with an earned run average under 3.00, Osteen was considered a top-notch starter and a workhorse. In those two years, Osteen and the Dodgers reached two straight World Series. In the 1965 World Series, the Dodgers went on to beat the Minnesota Twins in 7 games, with Osteen pitching 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 had lost their respective games. In the 1966 World Series, the Dodgers were beaten by the Baltimore Orioles in four games. Osteen was charged with the loss, in 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. In, Osteen reached his first All-Star game. His season totals included going 17–17, with a 3.22 ERA, in 288 innings pitched. He hurled 14 complete games, with five shutouts. In, 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, Osteen won 20 games for the first time and set a number of career highs, including 321 innings pitched, 183 strikeouts, 16 complete games, and 7 shutouts. In the 1970s, Osteen was still pitching an average of 260 innings a year. In the 1970 All-Star game, Osteen pitched three shutout innings, notching the win, in a game most remembered for the play in which Pete Rose barreled into Ray Fosse to score the winning run inthe 12th inning. Coincidentally, like Osteen, the pitcher and hitter involved in the walk-off single were also Tennessee natives: Jim Hickman collected the hit off losing pitcherClyde Wright. In, Osteen had a particularly strong year, finishing with 7 complete game victories in his last 9 starts. That year, he was 20–11, with a 2.64 ERA, in 252 innings pitched. Osteen made his 3rd and final All-Star team in 1973, in what would prove to be his last real quality MLB campaign — and his last season with the Dodgers. That year, while pitching for a 2nd-place Dodger team, Osteen went 16–11 and posted a 3.31 ERA, while logging 33 starts, 12 complete games, and 3 shutouts. He had achieved double-figure wins each year, for 10 consecutive seasons. Prior to the season, the Dodgers traded Osteen to the Houston Astros for outfielder Jimmy Wynn. Wynn helped the Dodgers win the 1974 NL pennant The Astros traded Osteen to the St. Louis Cardinals in August of 1974. On September 11, 1974 he pitched 9 innings of relief against the New York Mets in a 25 inning game, won by St. Louis 4-3. He did not figure in the decision. In April 1975, he was release by the Cardinals and was signed by the Chicago White Sox, for whom he played his final game on September 27, 1975. That following spring, when Osteen no longer fit in the ChiSox’ future plans, the team released him. Over the course of an 18-year professional career, Osteen compiled 196 wins, 1,612 strikeouts, and a 3.30 ERA. As a batter, Osteen had a lifetime.188 batting average, with 8 home runs, and 76 runs batted in. He was used as pinch hitter on a number of occasions. Defensively, he recorded a.971 fielding percentage which was 18 points higher than the league average at his position. Beginning in, Osteen became a big league pitching coach for the Cardinals, Philadelphia Phillies, Texas Rangers, and Dodgers. He also coached various minor league teams.
