Hillman entered the majors in 1955 with the Chicago Cubs, playing for them five years before joining the Boston Red Sox (1960–61), Cincinnati Reds (1962) and New York Mets (1962). In 1956 had a 21–7 record with a 3.38 earned run average while playing most of the season for the PCL Los Angeles Angels. \n', '

His most productive Major League season came in 1959 with the Cubs, when he posted career-numbers in appearances (39), wins (8), starts (24), complete games (4), strikeouts (88), and innings pitched (191). On May 6, 1959, at Forbes Field, he posted his only big-league shutout against Harvey Haddix and the Pittsburgh Pirates, 3–0, giving up two hits, walking one and striking out two. Strictly a reliever for the 1961 Red Sox, he went 3–2 with a 2.77 ERA in 78 innings and 28 games.\n', '

In an eight-season career, Hillman posted a 21–37 record with 296 strikeouts and a 3.87 ERA in 188 games pitched, including 64 starts, eight complete games, one shutout, 42 games finished, three saves, 185 walks, and 624 innings pitched. Along with his Cubs teammate Jim Marshall, Hillman was part of the very first inter-league trade without waivers in MLB history, when he went to the Boston Red Sox in return for Dick Gernert. The November 21, 1959, transaction was the first during a three-week period of trading permitted by a change in both leagues\' rules.\n', '

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