I've got 9,446 Cubs cards from 59 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1950s / 1960s: 1955 Bowman #229 Jim Brosnan Yea! The TV set! Brosnan pitched in 18 games as a rookie in 1954 and that was good enough for Bowman to include him in the '55 set. But it wasn't good enough for the Cubs to include him on their '55 roster. Instead, he spent the season in the minors and had a great year, going 17-10 with a 2.38 ERA. After the '55 season he would never pitch in the minors again. I never knew Brosnan as a pitcher. Instead, to me he was the author of this book...
...which I got when I was seven or eight and became a favorite of mine. Two Cubs, Ron Santo and Rich Nye, were among the little leaguers who became big leaguers.
1970s: 1976 Topps #334 Mike Garman This is a nasty looking card, with the scowl on Garman's face and a really bad airbrush job. Garman came to the Cubs from the Cardinals for Don Kessinger. With that trade, the final member of the '69 Cubs was gone. Garman had a horrible season in 1976, with a 2-4 record and 4.95 ERA out of the bullpen. After the season he was sent to LA in the trade that brought Bill Buckner to the Cubs.
1980s: 1989 Team Issued #33 Mitch Webster These cards were given away at Wrigley Field on August 10, 1989. The Cubs had just taken over first place three days earlier, on their way to the NL East crown. They lost to the Phillies on Baseball Card Day in a slugfest, falling 16-13. The Cubs blew a 10-3 3rd inning lead that day....oops! Webster went 1-5.
1990s: 1995 Leaf #163 Steve Trachsel The 1995 season was not a good one for Steve Trachsel as he suffered the dreaded Sophomore Slump. His record was 7-13 and his ERA was 5.15. Those are some horrible numbers! He did turn it around the next season, going 13-9 and lowering his ERA to 3.03.
2000s: 2009 T206 #208 Derrek Lee D-Lee had his last hurrah for the 2009 Cubs, putting up his best numbers since his career-best season in 2005. For 2009 he hit 35 HRs and drove in 111 runs while hitting .306. Topps wasn't too impressed with what Lee was doing, because his T206 card is just a recycled...
....2009 Allen and Ginter card.