[1] A native of Aurora, Illinois, Kipper, a left-hander, stood 6 feet 2 inches (1.88 m) tall and weighed 200 pounds (91 kg) during his active career.

After graduating from Aurora Central Catholic High School, he was selected by the California Angels with the eighth pick in the first round of the 1982 Major League Baseball Draft.

He made his MLB debut with the Angels in April 1985 at age 20, but was ineffective in two games pitched and was returned to the minor leagues.

[2][3] He would pitch in 247 games for the Pirates over all or parts of seven seasons (1985–91)—initially as a starter, but then as a relief specialist—before finishing his MLB career for the Minnesota Twins in 1992.

[4] Thirteen years later, on August 16, 2015, he was named Boston's interim bullpen coach, part of a chain reaction of moves driven by manager John Farrell's medical leave of absence for treatment of lymphoma.