1980s: 1982 Topps #508 Jody Davis Jo-Dee...Jo-Dee!! Davis became the Cubs starting catcher in 1982. He hit a respectable .261 with 12 HRs and 52 RBIs. He was also second in the league in assists by catchers
1990s: 1997 Flair #15 Kevin Orie For a couple years now we have been hearing about all the great prospects the Cubs are developing in their farm system. I am guardedly optimistic, but memories of Kevin Orie (and a host of other failed prospects) keep me from getting over-excited. Orie was going to be the third baseman for years to come. He hit .275 in 1997, but the next season was down almost 100 points and never recovered. He was traded away in July 1998.
2000s: 2002 Topps Total #127 Alan Benes Benes pitched in 10 games for the Cubs over the 2002 and 2003 seasons. With limited appearances, the only set that included him both seasons was total. However, even Total wasn't totally impressed....
2010s: 2013 Sega Card Gen #226 Nate Schierholtz Here's one from last year's Card Gen set. The cards were produced by Topps, but obviously there was no photoshopping going on.