The son of former Washington Senators shortstop Ron Stillwell, Kurt progressed through the Cincinnati Reds’ system with another promising shortstop, Barry Larkin, both vying to succeed Dave Concepcion. Although Stillwell performed well in 1987, the Reds traded him to the Kansas City Royals, who were desperate for an everyday shortstop, for Danny Jackson.
Stillwell responded in 1988 with his best offensive year, hitting ten home runs, driving in 53, and scoring 63 runs. He was particularly effective in the first half and was rewarded with a trip to the All-Star Game. Only 24 years old, Stillwell seemed destined for a successful major league career, and produced decent numbers in ’89. However, he failed to improve the next few years; his plate discipline suffered and he never walked more than 47 times in a single season.
The Royals elected not to re-sign Stillwell after the 1991 campaign, and he inked with the San Diego Padres on February 21, 1992. Handed the starting second base position, he struggled mightily and eventually lost his position to Tim Teufel.
