I've got 11,804 Cubs cards from 83 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1950s / 1960s: 1965 Topps #386 Cubs Rookies This is the second consecutive post that the RNG had pulled a rookie card from the '60s. Jaeckel was a converted infielder and he made four appearances at the end of the '64 season, prompting Topps to include him on a rookie card. But he never returned to the majors and this is his only card. Fred Norman was a lefty with a lot of promise but it took him almost ten years to finally become a decent pitcher. It wasn't during his time with the Cubs...or the A's...or the Dodgers...or the Cardinals...or the Padres. Things finally clicked for him when traded to the Reds in 1973.
1970s: 1972 Topps #335 Bill Hands After a subpar 1971 season, Hands bounced back nicely in 1972, going 11-8 with a 3.00 ERA. But wear and tear on his arm was starting to take a toll on him, and the Cubs sold high, trading him after the season to the Twins. Though traded up north to Minnesota, his career went south in a hurry and he was done after the 1975 season.
1980s: 1987 Fleer Glossy #556 Ron Cey Early print dates led to this '87 card of the Penguin with the Cubs, though he was traded to the A's in January, 1987 for Luis Quinones. He hit only .221 in Oakland and was released on July 15, ending his big league career.
1990s: 1995 Bowman #295 Randy Myers For the second time in three years, the Cubs closer lead the NL in saves in 1995, posting 38. The 1995 season was his last of a three year contract with the Cubs, and you would have thought he could have turned the three good years with the Cubs into an even bigger payday. But that's not how it turned out, as he signed a two-year deal with the Orioles that payed him less per season that what the Cubs paid him in 1995.
2000s: 2003 Donruss Team Heroes #118 Billy Williams This card comes from the player collection. It looks to be a picture from early spring in 1966 or 1967. The bleacher are behind him looks much different today. The catwalk is long gone, replaced today by expanded bleacher seating. And notice no basket either--it was just a plain 'ol ivy-covered wall.