Five Random Cubs Cards

 I've got 21,055 Cubs cards from 316 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.

1900s - 1970s: 1955 Bowman #247 Dutch Leonard The RNG gets us off to a great start with the Bowman TV set.  Leonard was the Cubs pitching coach.  The signing war between Bowman and Topps left both companies short of players, so they resorted to making cards for managers, coaches, and umpires to fill the sets.

1980s: 1988 Topps Traded #87 Jeff Pico  His major league debut was a start against the Reds on May 31, 1988.  Pico pitched a complete-game four hit shutout.  It was quite a debut and raised the bar for him quite high.  Maybe too high, because he never really delivered on the promise from that first start.

1990s: 1997 Finest #303 Ryne Sandberg This card is from the Competitors subset.  It is also designated Uncommon, which has the silver trim.  They were a bit scarcer than the common cards, with one in every four packs.

2000s: 2001 Fleer Ultra #28 Joe Girardi I always like a catcher action shot that shows him tossing the mask aside.  Plus there's a cameo by a Hall of Famer.

2010s: 2018 Heritage #171 Javier Baez  I don't know what is more distracting for me, the blond hair on Baez or the font in the circle that is smaller that the font on the original 1969 cards.  Both items look weird and out of place.