1900s - 1970: 1979 Topps #693 Dave Rader A halfway decent catcher with the Giants, by the time the Cubs got him in 1978 he was old and broken down. He hadn't been a full-time player since 1974, but that didn't stop the Cubs from making him their starter in '78. He wasn't very good and after the season he was traded to the Phillies as part of the Manny Trillo trade. He played in only 25 games for the 1979 Phillies.
1980s: 1985 Topps #72 Rick Sutcliffe (Autographed) This comes from my autograph collection. It could actually go with two different decades. The card is a 1985 Topps card, but it was part of the 2004 Signature Series. I put it with the 1985 cards since it is an actual card from that year. Topps just had Sutcliffe sign it, then it was numbered and a sticker was put on the back.
1990s: 1995 Conlon Collection #1409 Cliff Heathcote This card is from the final set of Conlon cards in 1995. Only 110 were issued instead of the 330 that had gone out each of the past several years. The cards featured gold-foil printing and a green border, both firsts for Conlon. The cards look much sharper than the plain black and white versions from previous years. Too bad it was Conlon's last set. The card itself is for baseball's all time highest scoring game. The Cubs beat the Phillies 26-23 on August 25, 1922. Heathcote went five for five and scored five runs, so he gets featured on the card.
2000s: 2001 Victory #334 Todd Hundley Hundley came to the 2001 Cubs with a big contract and high hopes. It was a waste of money and hope. He batted a minuscule .187
2010s: 2011 Topps #115 Kerry Wood Cognac The cognac parallels were one of several put out by Topps in their 60th anniversary year of 2011. I put together the base, platinum, gold, black, and cognac sets that year and haven't bothered with a parallel set since. After a year and a half away from the Cubs, Wood returned after expressing an interest in signing with the team while attending Ron Santo's funeral. The picture on the card is Wood acknowledging the cheers from the fans at the home opener.