I've got 8,917 Cubs cards from 52 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1950s / 1960s: Topps 1968 #235 Ron Santo For some reason I really like the look of the fake fielding pose on this card. In 1968 Santo made the All Star team for the fifth time and also won his fifth consecutive Gold Glove. He set a major league record by leading league third basemen in assists for the seventh consecutive season. Playing in all of the Cubs 162 games, he smashed 26 HRs and tied with Billy Williams for second in the NL in RBIs with 98.
1970s: Topps 1978 #17 Mike Krukow The 1978 set has a special place in my collection because it is the first complete set I bought. So I was familiar with all of the Cubs cards, including this spring training shot of Krukow. He started the season poorly and in May was sent to AAA. This had to be a letdown for a guy who spent all of the previous season with the Cubs. He seemed to turn things around because when he returned to the Cubs in late June he was placed into the rotation and went 9-3 the rest of the way.
1980s: Topps 1988 #593 Bob Tewksbury The Cubs acquired Tewksbury from the Yankees in a 1987 trade for Steve Trout. The righty was 0-4 with a 6.50 ERA with the Cubs. Some trade, huh? He started the season in AAA but was recalled in mid-May. He made only one appearance, giving up five runs in 3.1 innings. A few days later he was placed on the DL. When activated, he was sent back to AAA and spent the rest of the season in Iowa. He became a free agent after the season and was signed by the Cardinals, ending up with some success in St. Louis.
1990s: Stadium Club 1994 #359 Mike Morgan This is the third time the random number generator has picked a Mike Morgan card. The five seasons Morgan spent with the Cubs were the most of any of his stints with the 12 different teams he played for. The high point of his season was Opening Day, which he started. But he was bombed for six runs in four innings. Injured for much of the season, with three different stints on the DL, Morgan made only 14 more starts for the 1994 Cubs. And it wasn't pretty. He was 2-10 with an ERA 6.69 ERA.
2000s: Heritage 2010 #27 Mike Fontenot The 2010 season was Fontenot's last with the Cubs. The team's brass grew weary of the two LSU boys, and both Fontenot and Theriot were moved out of Chicago. Fontenot went to the Giants and even played in a World Series game.