Hillman made his MLB debut with the Chicago Cubs on April 30, 1955. During his tenure with the Cubs, he was known for his control and ability to keep hitters off balance. Although he was not a power pitcher, his finesse and strategic approach to pitching allowed him to compete effectively against some of the era's more formidable hitters. Hillman spent the majority of his major league career with the Cubs, playing with them until 1959.
In 1960, Hillman was traded to the Boston Red Sox, where he continued to showcase his pitching abilities. His time with the Red Sox was marked by a solid performance, although he often found himself in the role of a relief pitcher rather than a starter. This transition was indicative of the evolving strategies within baseball during that period, as teams increasingly relied on specialized roles for pitchers.
Hillman's career took another turn when he joined the Cincinnati Reds in 1962. His stint with the Reds was brief, but it provided him with the opportunity to be part of a team that was competitive in the National League. Later that same year, he was acquired by the New York Mets, an expansion team that was in its inaugural season. Hillman's experience was valuable to the fledgling team, although his time with the Mets was short-lived.
Throughout his career, Hillman was known for his professionalism and work ethic. He finished his major league career with a win-loss record of 21-37, an earned run average (ERA) of 3.87, and 296 strikeouts. While these statistics may not place him among the legends of the game, they reflect a solid career spent contributing to the teams he played for.
After retiring from professional baseball, Hillman returned to his roots in Virginia, where he lived a quiet life away from the spotlight of the major leagues.
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