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 he had a 21–7
record with a 3.38
earned run average while playing most of the season for the
PCL Los Angeles Angels. On September 14, 1957, in the second game of a double-header against the
Pittsburgh Pirates, Hillman pitched to Cub catcher
Jim Fanning, playing on their shared 30th birthdays. In 1959 with the Cubs, 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 threw 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. 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 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 unrestricted trading permitted by a change in both leagues' rules. ==Personal life and death==