I've got 7,696 Cubs cards from 37 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
The 50's / 60's: 1967 Topps #171 Cal Koonce He came to the Cubs as a 21-year-old in 1962 and spent most of the next few seasons working out of the bullpen. He made 34 appearances in 1967, going 2-2 with a 4.59 ERA before being sold to the Mets on August 2.
The '70's: 1971 Topps #280 Fergie Jenkins I never liked that so many Cubs cards had Shea Stadium in the background like this one does. Bad 1969 memories I guess. Well, this card was from Jenkins' pinnacle season with the Cubs. He won the NL Cy Young Award as he led the league in wins with 24 against 13 losses. Here's a stat you won't ever see again, in 39 starts, Jenkins had a league-leading 30 complete games. Yes, 30 complete games, which would be more than the entire Cubs team has had over the last six seasons!
The '80's: 1982 Donruss #126 Randy Martz He spent most of the 1982 season in the Cubs rotation, starting 24 games. Martz was 11-10 and impressed the Cubs brass so much that after the season he was traded to the White Sox in the trade that sent Steve Trout to the north side.
The '90's: 1990 Donruss #137 Mitch Webster Donruss blew it with this one as Webster was traded to the Indians on November 20, 1989. He hit .252 in 128 games for the Tribe.
The 2000's: 2006 Upper Deck #90 Derrek Lee This was the most disappointing season of Lee's career. He was coming off a career year in 2005 as he led the league in hitting (.335), smacked 46 homers and knocked in 107 runs; he was a serious Triple Crown threat for much of the season. But in Los Angeles on April 19, Lee broke his wrist in a first base collision with Rafael Furcal. He came back two months later, but was not the same. He later missed another month when it became obvious that he was still hurting. For the year he played in only 50 games and hit .286 with 8 HRs and 30 RBIs.