I've got 8,448 Cubs cards from 48 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1950s / 1960s - Topps 1959 #520 Don Elston: Elston was the Cubs workhorse out of the bullpen. In both 1958 and 1959 he led the National League in appearances. The best season of his career was probably 1959, a year which saw him make the All Star team. He pitched in 65 games, all in relief and finished 49 of those games. He was 10-8 with a 3.32 ERA. His 18 decisions seems like a lot compared to a reliever today.
1970s - SSPC 1976 #293 Mike Garman: SSPC didn't go for the airbrush thing. They did nothing to the front, but on the back of the card, Garman is listed as a Cub. He was acquired after the 1975 season in exchange for Don Kessinger (who was the last of the '69 Cubs to be traded). Garman was a reliever and in 1976 he stunk. His record was 2-4 with an ERA of 4.95. After the season he was traded to the Dodgers as a part of the Rick Monday / Bill Buckner trade.
1980s - Score 1988 #551 Jody Davis By the time this card came out, Jody Davis' career was just about finished. He played in only 88 games for the Cubs and lost his starting job to Damon Berryhill. He was traded to the Braves on the final weekend of the season. That seemed like a very strange time to make a trade. I wonder why they didn't wait until after the season? It's not like the Braves needed him for a pennant drive; they finished the season 54-106.
1990s - Bowman 1993 #648 Jeff Hartsock Who is Jeff Hartsock? That's a good question, because until I started working on this post, I had no idea! He had four September appearances for the Cubs in 1992, giving up seven runs in nine innings. After the season he was outrighted back to Iowa and wasn't even given an invite to the major league camp in the spring of 1993. He split time in AA and AAA before the Cubs let him go. The Giants picked him up and he finished the season with their AAA team.
2000s: Topps Traded 2008 #60 Jim Edmonds Starting the 2008 season with the Padres, Edmonds hit only .178 and was released on May 9. The Cubs signed him five days later and he spent the rest of the season as the Cubs regular center fielder. He showed decent power, hitting 19 homers in 85 games and hit .256.