I've got 6,607 Cubs cards from 23 different brands listed on a spreadsheet. The total has grown with the addition of 470 team-issued cards now on the list. A random number generator picked five cards, one each from the past several decades.
1950's / 1960's Topps 1964 #469 Cubs Rookies Both of these guys did pitch for the 1964 Cubs, though not very well. Norman made eight appearances, including five starts, and was 0-4 with a 6.54 ERA. He stuck around with the Cubs organization until he was traded after the 1967 season. Sterling Slaughter has a great name, though it sounds more like a WWE name than a baseball name. He made 20 less than sterling appearances in 1964, going 2-4 with a 5.75 ERA. He spent the next three seasons in the minors and never made it back to the majors.
1970's Topps 1978 #663 Paul Reuschel Rick's older brother (I've got more about the Reuschel brothers here.) had been with the Cubs since 1975. He was used in middle relief and put up solid, but unspectacular numbers. He pitched in 16 games for the 1978 Cubs and was then traded to the Indians on June 26. With the Tribe he was used in 18 more games including six starts.
1980's Topps 1984 #115T Rick Sutclliffe The Red Barron came to the Cubs from Cleveland just before the trading deadline in 1984, on June 13. He cost the Cubs their #1 prospect, Joe Carter, who would have a very good career. But it was worth the price as Sutcliffe led the Cubs to their first post season appearance since 1945. He was a remarkable 16-1 with the Cubs and won the NL Cy Young Award. His lone Cubs' loss came on June 29 to his former team, the Dodgers. After that, he was 14-0! It was an amazing and exciting run. The Cubs were in a fight for first and you knew that they would get a win at least once every five games. No long losing streaks here!
1990's Fleer Ultra 1994 #461 Derrick May May played in 100 of the Cubs 113 games in the strike-shortened season, mainly as the left fielder and usually hitting in the clean-up spot. He hit .284, but had only 10 HRs and 51 RBI's. That wasn't enough production for the #4 man, and he was cut by the Cubs the next spring.
2000's Upper Deck 2005 Moises Alou Upper Deck gives us a cool shot of Alou shattering his bat. Moises didn't play for the Cubs in 2005; instead he hooked up with his dad and played for the Giants. He had great numbers in 2004, cranking 39 HRs and knocking in 106 runs. But he was also 38 and I don't think the Cubs were willing to spend the big bucks to re-sign him. So all that offense was cut loose. With the Giants, he hit .321, with 19 HRs and 61 RBIs.