I've got 10,097 Cubs cards from 66 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1950s / 1960s Topps 1965 #402 Joe Amalfitano He saw his playing time sharply curtailed in 1965 as a rookie, Glenn Beckert, became the regular second baseman. In his new role as a utility infielder, he hit .271 in 67 games. By 1967 he was a coach with the Cubs and would manage the team at the end of the '79 season, the second half of the '80 season, and all of 1981. His .363 winning percentage is the worst in team history for any manager with over 50 games.
1970s Topps 1973 #603 Terry Hughes Hughes was a first round pick of the Cubs in 1967 and he is on a 1973 rookie card. That's a long wait, and not usually a good sign. Hughes actually played a few games for the Cubs in 1970, but then it was back to the minors. He was sold to the Cardinals just prior to the start of the 1973 season. Most of the year was spent in AAA Tulsa, though he did spend the last six weeks of the season with the Cardinals.
1980s Fleer 1988 #423 Scott Sanderson The picture on this card was taken in the early part of the season, as Sanderson was working in the Cubs bullpen before a game....that's a BP jersey that he's wearing. He had back surgery in February, 1988, and spent most of the season on the DL. He returned to the team in late August and made 11 relief appearances.
1990s Collectors Choice 1994 #290 Turk Wendell This card shows the flaky Wendell hopping over the foul line, something he did every time back and forth to the mound. He started the season with the Cubs, but after putting up a 7.04 ERA in 16 innings, he was sent to Iowa. He did much better as a starter in AAA, going 11-6 with a 2.95 ERA.
2000s Pro Debut 2010 #23 Ryan Flaherty We started today with a Cubs first round pick and finish with the same. Flaherty was the Cubs #1 in the 2008 draft. In 2010 he split his time between High A and AA. He had decent overall numbers, hitting .280 with 19 HRs and 88 RBIs. Last season was split between AA and AAA.