I've got 12,294 Cubs cards from 88 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1911 Turkey Red #33 Jake Pfeister With the ugliness that is 2014 Turkey Red, it's nice the the RNG picked an original Turkey Red. Keep in mind, though, that my cards from this era are not originals....the WW Finance Department doesn't allow for that! It's reprints for me! A member of the rotation for the World Champion 1907 and 1908 Cubs, Pfeister was done by the time Turkey Red was issued. The 1911 season was his last and he pitched in only six games. He was 1-4 with an ERA of 4.01. Yes, he was done.
1980s: 1981 Topps Stickers #152 Bill Caudill This sticker is from Topps' reentry into the sticker game in 1981. It looks like we've got a head shot of Caudill in Mesa. Caudill was coming off a decent 1980 season that saw him pitch in 72 games and have a really nice 2.19 ERA. Things blew up in 1981, though and he made only 30 appearance and saw his ERA skyrocket to 5.83. He was traded the next spring and ended up becoming the ace of the Mariners bullpen.
1990s: 1997 Fleer Traded #752 Jeremi Gonzalez Fleer included Gonzalez in their traded set based on the nice rookie season he turned in. He was called up to the Cubs in late May and spent the rest of the season in the starting rotation. He was 11-9 for the year and the 11 wins led the Cubs staff.
2000s: 2004 Topps Chrome #83 Hee Seop Choi He's with the Cubs in the 2004 Chrome set, but Choi was traded to the Marlins in November, 2003 for Derrek Lee. He was not missed.
2010s: 2010 Upper Deck #108 Kevin Gregg Here's a card from Upper Deck's non-MLB license set. This card is a nice example of why UD got themselves in trouble...you can clearly see the Cubs logo on the hat, the Chicago on the jersey, and the walking bear on his sleeve. I still can't figure how Upper Deck thought that they could get away with this. And the way the lawsuit was settled, it is nearly impossible for them to put out any baseball cards, even though they have a license with the Player's Association.