I've got 8,519 Cubs cards from 49 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
Pre-1970s: Turkey Red (reprint) 1911 #32 Orval Overall Overall was a twenty game winner for the 1909 Cubs, but must have been hurt in 1910, starting only 23 games. He was out of baseball in 1911 and 1912. He tried coming back in 1913, but wasn't very effective and his big league career was over.
1970s: SSPC 1978 #261 Ray Burris This card is from the SSPC All Star Gallery team album (I have previous posts on the album here and here). An innings eater, Burris was 44-39 from 1975-1977. He slumped badly in 1978 falling to 7-13 and was banished to the bullpen.
1980s: Topps 1982 #403 Jim Tracy Though featured as a Cub, Tracy was traded to the Astros during the winter of 1981. The #23 he wore was taken over by a newly acquired rookie, Ryne Sandberg. Tracy would never make it back to the major leagues.
1990s: Fleer Ultra 1991 Update #75 Rick Wilkins This is the fourth time a Rick Wilkins card has been selected by the random number generator. That's probably three too many! This card is from his rookie season of 1991. He didn't make the team in the spring, but an injury to Joe Girardi and ineffectiveness by back-up Erik Pappas led the Cubs to turn to Wilkins. After being called to the Cubs on June 4 (which also happened to be his birthday!), he played in a total of 86 games. He hit only .222 but did throw out 40% of those trying to steal.
2000s: Upper Deck 2001 #264 Sammy Sosa Season Highlights If the highlight of the season happens on April 20, then you didn't have a very good season. The 2000 Cubs didn't. They finished at the bottom of the NL Central with a record of 65-97. Sammy led the team with 50 homers, while the next closest on the team was Henry Rodriguez with 18.