I've got 6,607 Cubs cards from 23 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1950's / 1960's Topps 1967 #296 Glenn Beckert The Cubs second baseman had another solid season in 1967. He hit .280 and was the toughest player in the NL to strike out. He also sparkled in the field, leading all NL second baseman in putouts and was second in assists and double plays.
1970's Topps 1972 #556 Ron Santo In Action So is this card Ron Santo In Action or Dick Dietz In Action? Topps was still early in the action photo game, and they still needed a lot of work. In 1972 Santo played in only 133 games, his lowest total since his rookie season of 1960. A fractured right wrist in mid May was the problem. Still, he hit .302 and had 17 HRs and 74 RBIs.
1980's Team Issued 1986 Ryne Sandberg Ryno won his fourth straight Gold Glove and set an NL record for fewest errors in a season (5) and highest fielding average (.9938). He was the starting second baseman in the All-Star game.
1990's Upper Deck 1990 #345 Jerome Walton The 1989 NL Rookie of the Year was hit hard by the Sophomore Jinx in 1990. A broken right hand and an injured wrist cut his game total to only 101. His offense suffered as his average dropped 30 points from the previous season.
2000's Topps 2008 #37 Jason Marquis The righty was in the second year of a three year free agent deal he signed with the Cubs for over $20 million. It was a pretty hefty price for a #3/4 starter. Marquis was 11-9, though his ERA was 4.53. After the season the Cubs dumped his salary on the Rockies, though he had a decent season for Colorado.