1900s - 1970s: 1977 TCMA All Time Cubs Charlie Grimm Does Joe Maddon replace Grimm as the All Time Team manager? Grimm won three pennants but no titles. Maddon has the title, one pennant, and two (soon, hopefully three) division titles.
1980s: 1985 O'Connel & Sons Ink #62 Billy Williams This is card #62 in the set but my mind gets messed up every time I see that since Billy wore #26.
1990s: 1998 Circa #122 Mickey Morandini Circa put out some wild looking cards, didn't they!
2000s: 2000 Opening Day #93 Henry Rodriguez And how did Henry Rodriguez do on Opening Day, 2000? He was 0-3 but the Cubs beat the Mets 5-3 in a game played in the Tokyo Dome.
2010s: 2013 Team Issued Season Ticket Holders #80 Rick Sutcliffe This card was printed on tickets for game #80, which was on September 24. On that same date 29 years earlier, Rick Sutcliffe won his 14th consecutive game and the Cubs clinched the Eastern Division title. That was a great night!