I've got 18,633 Cubs cards from 259 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.1900s - 1970s: 1952 Topps #224 Bruce Edwards The RNG starts us out with a card from Topps' first set. In case you are wondering, the patch on his sleeve is for the National League's 75th anniversary, celebrated in 1951.1980s: 1982 Donruss #403 Bill Buckner That's a pretty decent action shot of Billy Buck at the bag.
1990s: 1990 Leaf #25 Greg Maddux Looks like Maddux is on the hill as the Cubs take on the Cardinals. My guess is that the picture is from June 10, 1989. He faced the Cardinals twice at Wrigley. The other game was in April and just 7,000 were at the game. The crowd in the picture looks way too big for that date. The June 10 game was not a good one, as he gave up six runs in 5 1/3 innings and took the loss.
2000s: 2005 Past Time Pennants #RH Randy Hundley I got this for my autograph collection. I'd like a certified autograph of as many of the '69 Cubs as I can get.
2010s: 2012 Bowman Sterling Steve Clevenger Autograph The RNG picks two autographs in a row. This one is for my rule-following collection, since Clevenger was with the Cubs in 2012. What a mess of an autograph he has compared to Randy Hundley's.