1900s - 1970s: 1959 Topps #388 Bob Will Topps pulled out a picture from 1957 for this 1959 card and they actually had a good reason: Will played in just six games for the Cubs in 1958. The rest of the year was spent in the minors. That does beg the question though, why was he included in the 1959 set??
1980s: 1986 Fleer Stickers #35 Leon Durham The Bull! By 1986 it was becoming clear that Durham was just an OK major leaguer, not the superstar we'd been hoping for. He topped 20 homers for the third straight season, but just barely (he hit 20). His average was .262 and he had 65 RBIs. Good, but not great.
1990s: 1994 Finest #330 Karl Rhodes Tuffy was Finest on Opening Day 1994, with three home runs, and then not much after that. From May 1 to the end of the season he hit just .201.
2000s: 2005 Topps Total #212 Todd Hollandsworth For most of the 2005 season Hollandsworth was the Cubs starting left fielder. He was pretty unspectacular, hitting ..254 with 5 HRs and 35 RBIs. The Cubs shipped him to the Braves in late August in exchange for two prospects that never made the majors.
2010s: 2014 Topps 1989 Mini Die Cut #98 Ryne Sandberg I'm glad the RNG picked a Sandberg card because he was in the news this week. He reportedly had lunch with Cubs owner Tom Ricketts. The rumor is that he's selling his home in Arizona and planning to move back to Chicago. It will be interesting to see if he ends up with a role in the Cubs organization. I don't see him as a coach (I think he's a bit too old school for Joe Maddon); maybe a front office job?