I've got 10,707 Cubs cards from 71 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1950s / 1960s: 1951 Bowman #211 Hal Jeffcoat At this point in his career, Jeffcoat was a part-time outfielder for the Cubs. He played in 113 games for the 1951 Cubs and hit .273. Three years later he would switch positions and become a pitcher.
1970s: 1976 Topps #617 Darold Knowles For some reason, I've always really liked the look of this card. Its shot at an angle you didn't see used very often, more to the side than straight on. The home whites are a plus and the spring training background is nice, too. Knowles began the 1976 season as the Cubs closer. But by the end of the season, a rookie with a trick pitch named Bruce Sutter took over that role and Knowles was traded the next spring to the Rangers.
1980s: 1988 Star '88 #8 Andre Dawson So who's idea was it to make pink cards? Not a good look! Star was just starting to amp up their production in 1988. Dawson was one of nineteen players included in Star '88. Though his average was up in 1988 compared to his MVP 1987 season (.303/.287), his power and run production dropped. Home runs went from 49 to 24 and RBIs fell from 137 to 79. He did win his eighth Gold Glove and started the All Star game for the second consecutive year.
1990s: 1997 Leaf #82 Mel Rojas The Cubs signed Rojas as a free agent for the 1997 season and were full of optimism. For the Expos in 1996 he recorded a career high 36 saves. He was a bust for the Cubs, though, saving only 13 games in 54 appearances. His record was 0-4 with a 4.42 ERA and he was traded to the Mets in early August.
2000s: 2001 Pacific #86 Kevin Tapani Tapani was tapped out by the 2001 season. He started 29 games, posting a record of 9-14 with an ERA of 4.49. He became a free agent after the season and the Cubs let him go. No other team showed an interest in him, so he hung 'em up.