1900s - 1970s: 1969 Milton Bradley Ron Santo I've got a post on the complete set of teh 1969 MB game here. This picture of Santo is a headshot from the Cubs PR department. The same picture (with the logo on the hat) is in the 1969 roster book.
1980s: 1988 Fleer #430 Wade Rowdon The Cubs brought Rowdon up in September, 1987 after he had a monster season in AAA (.337, 18 HR, 113 RBI). He played in 11 games and that was good enough for Fleer to included him as a Cub in the 1988 set. The Cubs weren't as impressed as Fleer and traded him to the Orioles at the end of spring trainning, 1988. He spent the first three months of the season with Baltimore, hit an even .100, and finished the rest of the year in AAA. The Orioles released him after the season, ending his professional career.
1990s: 1992 Leaf #72 Joe Girardi Leaf has the position letter awfully close to his last name. It looks like his name is Joe Girardic.
2000s: 2006 Turkey Red #458 Aramis Ramirez His career was peaking when this card came out. In 2006 Ramirez had career highs in home runs (38) and RBIs (119). He also hit a very productive .291.
2010s: 2014 Heritage #220 Junior Lake Lake seemed to turn up in just about every set last year. He had a semi-decent rookie season in 2013 (though he really tailed off at the end of the season) and Topps went all-in on Junior Lake. The Lake level dropped significantly last year and he's not a sure bet to even make the team in 2015.