Hillman played high school ball at Homewood-Flossmoor in suburban Chicago, and then collegiately at Eastern Illinois University. He pitched his entire 3-year MLB career with the New York Mets (1992–1994). After his MLB career, he pitched in NPB from 1995 to 1998 for the Chiba Lotte Marines and the Yomiuri Giants. Hillman was tied with fellow pitcher Randy Johnson for the tallest player in league history at 6 ft 10 in (2.08 m), before later being passed by 6 ft 11 in (2.11 m) Jon Rauch.
Hillman worked as an analyst for FSN Rocky Mountain's coverage of the Colorado Rockies between 2005 and 2008.
Hillman also played four seasons in Japan. He played first with the Chiba Lotte Marines where Bobby Valentine was manager. In 1995, his first season in Japan, Hillman had 12 wins and 9 losses. In 1996, he logged 14 wins and 9 losses and was voted the best nine. Hillman was also voted MVP of the 1996 All-Star game. In 1997, the Yomiuri Giants purchased his contract, signing him to a $7.5 million, two-year deal. The Giants expected him to be a key player in their quest for a championship.

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