Tim Wakefield through the years
Wakefield was drafted by the Pittsburgh Pirates in the eighth round of the 1988 amateur draft. He made his major league debut in 1992 for the Pirates and finished third in NL Rookie of the Year voting after compiling an 8-1 record with a 2.15 ERA over 92 innings. Wakefield started twice in the 1992 NLCS, once in Game 3 with the Pirates down 2-0 in the series, and again in Game 6 with Pittsburgh down 3-2. The rookie threw two complete games and beat Atlanta's Tom Glavine twice.
Wakefield struggled in his second season with the Pirates, going 6-11 with a 5.61 ERA. Wakefield spent most of 1994 with Triple-A Buffalo. He was released by the Pirates on April 20, 1995 and signed with the Red Sox six days later.