1980s: 1989 Topps #262 Jeff Pico Pico spent most of the season working middle relief for the '89 Cubs. He made 53 appearances, all but five from the bullpen. His record was 3-1 with an ERA of 3.77. The Cubs media guide mentions that he allowed 19 of 41 inherited runners to score. When half of your inherited runners score, I'd think you'd like to keep that quiet; it doesn't seem like something to write about.
1990s: 1990 Topps TV #49 Jeff Hearron The 1990 Topps TV Cubs set was a 66 card set that was available only by ordering in off of a TV commerical. To get to 66 cards, the set included several Cubs prospects, and Jeff Hearron was one of them. Hearron was drafted by the Blue Jays in 1983 and had brief stints in Toronto in both 1985 and 1986. By 1990, he was with his third organization in three years. He spent the entire season in AAA and hit just .235. That was his final season in organized ball.
2000s: 2004 Opening Day #111 Kenny Lofton The speedy center fielder didn't play with the Cubs on Opening Day or any day in the 2004 season. He came to the team from the Pirates during the 2003 season and really provided some spark at the top of the lineup. But he was a free agent after the season and the Cubs let him go. He spent the 2004 season with the Yankees.
2010s: 2011 Topps Limited Edition Factory Set #309 Team Card This card came from the factory set that could be earned as a prize in the 2011 Diamond giveaway that Topps ran. I didn't earn the prize but I did buy a Cubs team set.