1950s / 1960s: 1960 Fleer #9 Mordecai Brown We begin today with a card from Fleer's 1960 Baseball Greats set. I like the fact that Fleer colorized the picture.
1970s: 1978 SSPC #266 Dave Roberts The journeyman lefty spend a season and a half with the Cubs, including the entire 1978 season. He split he time between the rotation and the pen, starting 20 games and relieving in 15 more. He ended the year with a 6-8 record and a 5.25 ERA. He was eligible for free agency at the end of the season and the Cubs didn't bother offering him a contract.
1980s: 1989 Team Issue #4 Don Zimmer This card is part of a set given away at Wrigley Field on August 10. Zimmer led the surprising '89 team to the NL East title, as they picked up 16 more wins than in '88.
1990s: 1998 Topps #108 Kevin Orie One in a long line of young busts at third base, the Cubs gave up on Orie after two thirds of the season and traded him to the Marlins. He was hitting only .181 at the time of the trade.
2000s: 2011 Pro Debut #292 Nicholas Struck Not very often does a 38th round pick get included in Pro Debut, but here's one, Nick Struck. He split the 2013 season between AAA and AA, going 7-12 between the two. I'd be surprised if he ever makes it to Wrigley.