I've got 12,642 Cubs cards from 92 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1953 Bowman #71 Paul Minner As plain as they are, the '53 Bowman cards sure do look nice. This card has Minner is the standard pitcher pose at the Polo Grounds in New York. Minner was a so-so starter on a very so-so Cubs team. He was 12-15 while the team was 65-89.
1980s: 1989 Topps #439 Frank DiPino Though shown as a Cub, DiPino wasn't with the 1989 Cubs. In 1988 he was just 2-3 with a 4.98 ERA. He was a free agent after the season and the Cubs had no interest in re-signing him. It made sense when you see those '88 numbers. He was signed instead by the Cardinals and he had the best year of his career, posting a perfect 9-0 record and an ERA of 2.45.
1990s: 1990 Star Silver #18 Mark Grace Star included three Cubs in the 1990 Silver set. Grace was a big deal in 1990 after hitting .647 in the 1989 NLCS. He played well in 1990, hitting .309 which was good for sixth in the league.
2000s: 2002 Topps #603 Todd Hundley If you are looking for a definition of free agent bust, see Todd Hundley. The Cubs signed him to a four year, $23.5 million deal starting with the 2001 season. He ended up with the team for just two years and had a combined average of .199. The shocking thing was that they were able to trade him after 2002, while he still had $13.5 million left on his deal. The Cubs were nuts for signing him but the Dodgers were even nuttier for making a trade for him.
2010s: 2010 Topps Peak Performance GU Derrek Lee Topps was cranking out GUs for Cubs at a crazy level in 2010. This card is from series two; Lee also had one in the first series. The 2010 season was DLee's last with the Cubs. After hitting .251 in 109 games, he was traded to the Braves for three guys that never got a whiff of major league baseball.