I've got 13,885 Cubs cards from 105 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1952 Topps #295 Phil Cavarretta We get one from Topps' initial, iconic 1952 set. Cavarretta was a player/manager in 1952 and he led the Cubs to a 77-77 finish...500 right on the nose. It was the Cubs most wins since 1946.
1980s: 1989 Fleer #421 Jody Davis Fleer must have had a very early deadline for their 1989 set because the Cubs had traded Jody to the Braves at the tail end of the 1988 season. Though only 32 in 1989, Jody was worn out and done. He hit just .169 for Atlanta
1990s: 1993 Flair #18 Mike Morgan This comes from Flair's initial release, which was not iconic. The backgound of the card looks odd, as they chopped off half of the ivy-covered wall and replaced it with blue.
2000s: 2002 Big League Heroes #302 Kerry Wood Here's one from my relic collection. The card shows Wood in the home pinstripes and the blue alternate, while the jersey piece comes from the road grays.
2010s: 2011 Topps Chrome Red #207 Darwin Barney I've got fifteen different versions of this card. The red is /25.