1900s - 1970s: 1952 Topps #16 Gene Hermanski From the iconic set that started it all, we have a picture of Gene Hermanski at Ebbets Field. Hermanski was a career part timer. He played in 99 games for the '52 Cubs, hitting .255 with 4 HRs and 34 RBIs.
1980s: 1988 Fleer Exciting Stars #13 Andre Dawson My initial thought was that the picture was taken on opening day in 1987 because of the bunting on the wall. But everyone is in short sleeves and on April 7 that's not very likely. The high temperature along the lake that day was only 49°. Most likely the picture is from July 4, 1987.
1990s: 1996 Topps Finest #316 Brooks Kieschnick Prodigy? Not really. Bust would be more like it. And Kris Bryant ≠ Brooks Kieschnick!
2000s: 2004 Bowman #251 Tony Richie The 2004 season was the peak of his career, as Ritchie hit .314 for Boise in low A ball. He moved through the system in the following years and did make it to AAA for two years. Most of that time was as a backup, and backup AAA catchers usually don't make it to the majors. Richie never did.
2010s: 2013 Team Issued Season Tickets #5 Shawon Dunston This is the season ticket holder version of the cards given out at Wrigley during the 2013 season. Dunston wore #12 and the card was given away on April 12.