1950s/1960s: 1954 Topps #60 Frank Baumholtz Like so many players from his generation, Baumholtz came to the major leagues at an older age due to military service in World War II. He was a 28 year old rookie for the Reds in 1947. The Cubs picked him up a couple years later, and by 1954 he was an aging part time outfielder. He played in 90 games and hit .297
1980s: 1988 Fleer Glossy #414 Jody Davis This is a nice action shot of Davis tagging out some Cardinal. I can't tell exactly who the Cardinal is, but he is wearing one of those big arm bands with the picture patch. The 1988 season was Jody's last with the Cubs. The wear and tear of being an everyday catcher had caught up with him and his numbers were dropping. He played in only 88 games for the Cubs before he was traded to the Braves at the tail end of the season.
1990s: 1990 Big #109 Mitch Williams I liked these Big cards! Wild Thing was riding high into the 1990 season, having helped pitch the Cubs to the division crown in 1989. But a knee injury limited him to 59 games. He was 1-8 and saved only 16 games.
2000s: 2005 Donruss Elite Turn Of the Century #157 Ernie Banks This card is from my player collection. There's an overused picture of Ernie from 1969, but at least Donruss got the Cubs logo correct, using the one with the small blue circle that was the Cubs primary logo in the late '60s and most of the '70s.