I've got 8,476 Cubs cards from 49 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1950s / 1960s: Topps 1958 #201 Jim Bolger Have you ever heard of this guy before? I didn't know too much about him. Bolger broke into the big leagues as an 18 year old for the Reds in 1950 (he played in two games). After brief stints in '51 and '54, the Reds sent his to the Cubs after the 1954 season. He played part-time for the '55 and '57 Cubs, with a career high 112 game in 1957. In 1958 he saw his playing time drop to 84 games because his average dropped to .225, 50 points lower than the season before. He was sent to the Indians over the winter.
1970s: Topps 1977 #639 Jerry Morales Jerry was a pretty hairy guy in 1976, what with the long hair, bushy eyebrows, and mustache. His best big league season was 1977, the only time he made the All Star team. He hit a career high .290 and added 11 HR and 69 RBIs. The Cubs brass was so impressed with his season that they traded him to the Cardinals over the winter.
1980s: Fleer 1983 #490 Doug Bird He didn't even suit up for the 1983 Cubs. After a 1982 season that saw his go 9-14 with a 5.14 ERA, he was traded to the Red Sox. For the 1983 Bosox, he was 1-4 with a 6.65 ERA. That was the last season in his 11 year career. The bird flew off into the sunset.
1990s: Collectors Choice Traded 1997 #7 Terry Mulholland The Cubs signed Mullholand as a free agent after the 1996 season. The Cubs were desperate for a left-handed starter; Mullholand would be their first lefty starter since Greg Hibbard started a game on September 29, 1993. That means no lefty starter from 1994 - 1996, three straight seasons. They should have stuck with all righties, since southpaw Mullholand was 6-12 with an ERA of 4.07 in 25 starts. The Cubs let him leave after the season.
2000s: Donruss 2004 Classics #167 Ernie Banks This beauty is from Donruss' Classics set. Each card in the set is numbered to 1999....did someone forget to tell Donruss that it was now 2004? Mine is #0082.