1959s / 1960s: Topps 1960 #27 Dick Drott Bursting onto the scene as a 20-year-old rookie in 1957, Drott posted a 15-11 record for the Cubs. But that was his peak season, and three years later he was 0-6 with a 7.16 ERA.
1970s: Topps 1975 #233 Billy Grabarkewitz This is a nasty airbrushed card, as the Cubs picked Grabarkewitz up from the Phillies midway through the 1974 season. He was the first player to wear #10 after Ron Santo was traded to the Sox, but Grabarkewitz was no Ron Santo. He didn't even make the Cubs team in 1975, being released at the end of spring training. The A's picked him up and he played in only six April games before getting sent to AAA, where he spent the rest of the season.
1980s: Donruss 1989 #513 Jeff Pico Pico spent the 1989 season pitching middle relief and making an occasional start. He had a total of 51 appearances and was 3-1 with a 3.71 ERA. He would last one more season with the Cubs before spending the next couple seasons in AAA.
1990s: Upper Deck 1994 #199 Kevin Roberson He sure looks cocky in this picture. I guess that when you hit .194 in 1993 you're entitled to be cocky. He followed that up with a robust .218 average in 1994.
2000s: Topps Update 2009 #39 Jake Fox He was a classic Cubs prospect, a one tool player. No speed, no glove, but he could hit with power (or strike out). Fox got a decent amount of playing time in 2009, getting into 82 games. But he was a man without a position. He didn't have the speed or glove to play the outfield, and he wasn't going to displace Derrek Lee at first. But when the Cubs played an AL team at their park, Fox was ready to DH. After the season he was traded to the A's for a couple unknown prospects.