I've got 11,263 Cubs cards from 77 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1950s / 1960s: 1959 Topps #538 Chick King I must confess that this is one Cub that I knew absolutely nothing about. I checked both the '58 and '59 roster books and he wasn't included in either. Baseballreference told me why he was missing...he played in only 8 games for the '58 Cubs and 12 for the team in 1959 before being sent to the Cardinals in a mid-May trade. I wonder why Topps included him in the '59 set after playing in only 8 games for the Cubs the year before?
1970s: 1978 Kelloggs #44 Steve Ontiveros Ontiveros hit a career high .299 in 1977, good enough for Kelloggs to make him one of three Cubs in the '78 set. He got off to a horrible start in 1978, hitting .145 in April and .178 in May. He finally snapped out of it in June, with a .376 average. His season came to an end in July when he dislocated his shoulder for a second time . Surgery put him on the shelf the rest of the campaign.
1980s: 1981 Topps #17 Bill Buckner Billy Buck had a really good year in the strike-shortened 1981 season. He hit .312 (his third .300+ season in four years), led the league in doubles (35), was second in hits (131), third in RBIs (75) , and fifth in average. He was named to the NL All Star team for the only time in his career and was 0-1.
1990s: 1993 Bowman #524 Rick Wilkins Rick Wilkins had one of the best seasons ever by a Cubs catcher in 1993. He hit .303 with 30 homers and 73 RBIs. He became one of only seven catchers in MLB history to hit over .300 with 30+ homers. Not only was he a stud with the bat, but he led NL catchers with a .421 caught-stealing percentage and was second in fielding with a .996 average. He would never again come even close to matching this season.
2000s: 2002 Fleer Tradition #7 Jon Lieber Lieber payed the price for a 20 win season in 2001 by blowing out his elbow in 2002. He was 6-8 before being shut down in early August. Tommy John surgery followed had he missed the entire 2003 season.