I've got 6,894 Cubs cards from 30 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1950's / 1960's - 1952 Bowman #88 Bruce Edwards Edwards came to the Cubs on June 15, 1951 in a trade with the Dodgers. Each team sent four players to the other team. That is something you don't ever see any more. Somehow, he made the NL 1951 All-Star team, though he hit only .237 in 68 games for the entire season. In 1952 he played in only 52 games. He went back to the minors in 1953.
1970's - 1971 Topps #203 Larry Gura This card gives us one of the standard pitchers' poses, taken at Shea. Gura was a second round pick in the 1969 draft and the Cubs rushed his development. He made his big league debut barely a year later, in April, 1970. He spent most of 1971 in AAA, making only six September appearances.
1980's - 1989 Donruss #223 Rick Sutcliffe 1989 would be Sutcliffe's last hurrah with the Cubs. By this time he was no longer the ace of the staff. Greg Maddux and Mike Bielecki had surpassed him. But in 1989, he went 16-11 as the Cubs won the NL East crown. He started game 3 of the NLCS against the Giants and left after 6 innings with the Cubs leading 4-3, but the bullpen couldn't hold the lead and the Cubs lost 5-4.
1990's - 1991 Fleer #709 Ryne Sandberg Home Run Kings That would be Ryno and Prince's dad, a much skinnier man than his son. This picture would have been taken at the 1990 All-Star Game, which was held at Wrigley Field. Fielder led the AL in homers in 1990 with 51, while Sandberg was the NL leader with 40.
2000's - 2005 Upper Deck #293 Mark Prior 2005 was his last full season in the majors, though he spent most of June on the disabled list. A line drive to the elbow landed him there. For the season he was 11-7 with a 3.64 ERA.