1950s / 1960s: 1961 Topps #533 Jack Curtis Whenever I see this card, I think of...
....John Belushi. Curtis made the jump for AA to the majors in 1961, spending the entire year with the Cubs. Mainly a starter, he was 10-13 and finished third in Rookie of the Year voting. He was also named to the All Star team....as the batting practice pitcher. I had never heard of that before.
1970s: 1971 Topps #410 Ken Holtzman The Cubs lefty is striking his tough guy pose at Shea Stadium. The 1971 season would be his last with the Cubs for a while. He slumped to a 9-15 record and his ERA ballooned to 4.48. After the season he was traded to the A's for Rick Monday.
1980s: 1989 Topps #668 Mike Bielecki Bielecki had a career year for the Cubs in 1989. He set career bests in wins (18), innings (212.1), starts (33), and strikeouts (147). In my mind he was the ace of the staff for the division winning Cubs. He made two starts in the NLCS, winning game 2 and taking a tough 3-2 loss in game 5.
1990s: 1994 Pinnacle #262 Brooks Kieschnick This is one of 35 different cards I have of a guy that played in only 64 games for the Cubs. He was one a many touted draft picks that went bust. He's probably best known for becoming a pitcher later in his career but still being used as a pinch hitter too.
2000s: 2008 Topps #365 Derrek Lee The RNG picked good ol' Derrek Lee with the final selection. The 2008 season was probably the final decent season of Lee's career. He hit .291 with 20 HRs and 90 RBIs. He got off to a really good start, belting 8 homers in April. But his power seemed to disappear after that.