I've got 12,189 Cubs cards from 87 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1915 Cracker Jack #17 Roger Bresnahan My card is from a reprint set. One of these in poor condition will set you back a hundred bucks. Bresnahan was the Cub's player-manager for the 1915 season, but lost his job when the Federal League folded and Joe Tinker became available.
1980s: 1983 Fleer # 500 Junior Kennedy Obviously Fleer did not give the 100-numbered cards to superstars. Strictly a utility player, with Cey, Bowa, and Sandberg anchoring the infield, Kennedy saw very limited action. He played in only 17 games through July 22 when the Cubs DFA'ed him. No team picked him up, and that was the end of Kennedy's career.
1990s: 1994 Topps #698 Willie Wilson Most people associate Willie Wilson with the Royals. But the final two seasons of his career were spent with the Cubs. Known as a speedy Royal, his legs were gone by the time the Cubs signed him for the 1993 season. He stole only seven bases, a career low. By mid-May of 1994 the Cubs gave up on him and released him, which ended his big league career.
2000s: 2007 Upper Deck #7 Scott Moore Topps has retired card #7 to honor Mickey Mantle. Upper Deck gave card #7 to Scott Moore. Upper Deck is now irrelevant in the hobby. Any connection??
2010s: 2013 Pinnacle #180 Chris Rusin The lefty is having a really nice spring as he competes for the #5 spot in the rotation. Last year he made 13 starts for the Cubs and was 2-6 with a fairly decent ERA of 3.93.