I've got 12,729 Cubs cards from 102 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1949 Bowman #52 Johnny Schmitz This card is a reprint; I don't have the actual cards of the early Bowman sets. The 1949 season for Schmitz was a letdown. He posted a record of 11-13 after going 18-13 the previous year. His ERA took a turn for the worse too, going from 2.64 to 4.35.
1980s: 1986 Donruss #311 Shawon Dunston This is one of just a few posed shots of Dunston that doesn't show him with a big, happy grin. He's got more of a pained look on this one. The 1986 season was his first full year in the big leagues and he led NL shortstops with 17 HRs. His 68 RBIs were the most by a Cubs shortstop since Ernie Banks drove in 80 in 1960.
1990s: 1996 Fleer #320 Jose Hernandez The RNG was in the shortstop mood today. Hernandez was the Cubs everyday shortstop after Dunston got hurt and left the team. He's even wearing the big red sweatbands like Dunston used to wear.
2000s: 2002 Upper Deck #312 Tom Gordon Flash spent just half of the 2002 season with the Cubs. He was 1-1 with no saves and an ERA of 3.42 when the Cubs traded him to the Astros on August 22.
2010s: 2013 Heritage #421 Welington Castillo Beef! Castillo became the Cubs full time catcher in 2013 and put up respectable numbers, hitting .274 with 8 HRs and 32 RBIs in 113 games. He had the highest defensive WAR among all major league catchers, 2.8.