I've got 19,484 Cubs cards from 285 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1963 Post #175 Don Landrum The Post cards had lots of their Cubs pictures, like this one, taken at Wrigley Field. That wasn't the case with the Topps cards of this era.
1980s: 1989 Team Issued Vance Law You typically think of third base as a power position. Not with Vance Law. He hit 7 homers. The Cubs released him after the season so he could sign with a Japanese team.
1990s: 1996 Bowman #348 Brian Stephenson Bowman really blew it with this one! Stephenson spent the 1996 season in AA and was 5-13 with and ERA of 4.69. Those are not the numbers of a good prospect. He never rose above AA.
2000s: 2000 Bowman #273 Ruben Quevedo Here's another big miss. Quevedo spent the 2000 season with the Cubs and posted a record of 3-10 and a Jumbo Jet ERA of 7.47