I've got 11,951 Cubs cards from 86 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1977 Topps #395 Manny Trillo Trillo, like the Cubs team, got off to a great start in 1977. He led the league in batting through the first half of the season, just like the Cubs were leading the division. His strong first half earned him a berth on the NL All Star team. Both Manny and the Cubs cooled off in the second half. Manny ended up with a .280 average and the team finished in fourth place.
1980s: 1984 Donruss #41 Joe Carter Donruss gave Carter the rated rookie tag as he was tearing things up in the minors in both '82 and '83. He was having a decent season in AAA in 1984 when the Cubs sent him to the Indians in the Rick Sutcliffe trade. The deal was one of those rare win/win trades for each team.
1990s: 1998 Stadium Club #340 Kerry Wood This card was from Wood's breakout 1998 season. I wasn't collecting much in 1998, so I don't know at what time of year Stadium Club was released. Was Topps lucky for including him in the set or was he a late addition?
2000s: 2005 Donruss Diamond Kings HOF Heroes #81 Ernie Banks This card comes from my Ernie Banks player collection. It is one of 100 in the set. These monochrome type cards are not among my favorites. I want more color!
2010s: 2012 T206 #277 Johnny Evers The 2010 set was Topps' last T206 set...good! There is only so much you can do when ripping off an iconic set like the original T206.