I've got 13,651 Cubs cards from 105 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1956 Topps #227 Russ Meyer The righty went from the Penthouse to the outhouse... he was 6-1 with the World Series champion Dodgers in 1955. Traded to the Cubs over the winter, he was 1-6 and then waived by the Cubs in September.
1980s: 1989 Score #360 Darrin Jackson After hitting just .229 for the 1989 Cubs in 70 games, Jackson was traded to the Padres. He did even worse there, hitting .207. But an even worse fate was ahead for Jackson: years in the White Sox broadcast booth with Ken Harrelson and then Ed Farmer.
1990s: 1991 Star Nova #80 Ryne Sandberg This is one of 175 different Star cards of Ryne Sandberg in my collection. It looks like he's taking some grounders before an early Spring game.
2000s: 2003 Fan Favorites #30 Ernie Banks Why would Topps use such and ugly card for a Fan Favorite?
2010s: 2013 Aunt Millies #5 Back to Back Central Division Championships Remember the good 'ol days when the Cubs were winning? I miss those. I hope they return soon, like this year!