1900s - 1970s: 1909 T206 Jimmy Sheckard (no glove) This is one of two cards of Sheckard in the set, hence the "no glove" designation. He was the left fielder for four pennant winning Cubs teams.
1980s: 1984 Fleer #505 Lee Smith That is an odd-looking logoless jacket that Smith is wearing. Smith picked up 33 saves and nine wins as the Cubs closer in 1984.
1990s: 1991 Fleer Ultra #67 Luis Salazar This card comes from Ultra's debut set. It looks like Salazar is swinging with his eyes closed. He played in 103 games for the '91 Cubs and equaled his career high in homers with 14.
2000s: 2002 SP Authentic #141 Francis Beltran This is one of the rookie autograph cards that were part of the base set. Sure looks like Francis could use a little help with his penmanship.
2010s: 2013 Team Issued #14 Ernie Banks No, I didn't cheat... the RNG really pulled this one! Ernie got card #14 in the Cubs massive 163-card set that was given away during the 2013 season. The red box seat dividers in the background tell me this picture was taken at Seals Stadium in San Francisco. The 1959 set has several Cubs players in San Francisco, so I'd guess this was taken at the same time during the 1958 season.