I've got 9,070 Cubs cards from 54 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1950s / 1960s: 1958 Topps #135 Moe Drabowsky I'm not sure how Topps could mix up "Moe" and "Mike," but they did. The error went uncorrected, though the next season he was "Moe." In 1958, Mr. Drabowsky went 9-11. He had an arm injury that limited his appearances in the second half of the season. Here's how bad the Cubs were at the time: Moe had 24 career NL wins after 1958, which was tops on the Cubs staff. The pitching staff was very young/very bad.
1970s: Topps 1973 # 552 J.C. Martin Martin is on the list of players who played for both the Cubs and the Sox. He was with the Sox at the start of his career, from 1959-1967. By the time he got to the Cubs in 1970, he was a broken-down back-up catcher. The Cubs got him just before the season, and when Randy Hundley went down with a season ending knee injury, he became one of several catchers who tried to fill Hundley's position. By 1972, Martin saw limited action, appearing in only 25 games. He was released by the Cubs at the end of spring training in 1973. He spent about half the season in AAA, but hung them up for good after playing in only 53 games.
1980s: Kenner Starting Lineup 1989 #18 Billy Williams This card came with a dual player action figure set; Billy was paired up with Ernie Banks. Here is what the package looks like:
I've got both the Ernie and Billy cards, but not the figures. Some day.
1990s: Star Nova 1992 #59 Ryne Sandberg This card came from one of the bazillion sets Star put out. Right now, I've got 12 of the 19 different Sandberg sets from Star. Unfortunately I've been stuck on that number for a while too. None of the sets I need have popped up on ebay in the last year. Ryno had a decent year in 1992, hitting .304 with 26 HRs and 87 RBIs. He also led NL second baseman in assists and total chances, but saw his streak of nine straight Gold Gloves come to an end.
2000s: Topps 2004 #514 Todd Hollandsworth As a member of the Marlins, Hollandsworth was 3-3 in the 2003 NLCS against the Cubs. The Cubs figured if you can't beat him, sign him. He came to the Cubs as a free agent, hoping to bolster the 2004 Cubs bench. He was hitting .318, but on June 27 he fouled a ball off of his shin and that injury sidelined him for the rest of the season.