1900s - 1970s: 1973 Topps #180 Fergie Jenkins The 1973 season was Fergie's worst, and last, as a Cub. His streak of six straight 20+ win seasons ended as he went 14-16. In August he had a melt down, throwing bats into the Wrigley Field grandstands after being booed for another poor performance. (You can read about it from the Tribune here, and while you're at it, scan through the entire paper from that day.... a fun trip down memory lane) After the season Fergie was shipped off to the Rangers.
1980s: 1985 Leaf #166 Rich Bordi The righty didn't even play for the '85 Cubs. He was traded to the Yankees in December, 1984.
1990s: 1993 Bowman #524 Rick Wilkins The mask flies off as Wilkins makes the throw to second. The 1993 season was the season for him. He had career highs in average (.303), home runs (30), and RBIs (73). He never came close to duplicating those numbers.
2000s: 2008 SP Legendary Cuts #160 Billy Williams A second '69 Cub! The picture on the background of his swinging at Shea Stadium has shown up on many cards. The color portrait seems less used; in fact I couldn't find another card in my collection with the same picture.
2010s: 2012 Gypsy Queen #347 Ernie Banks Mini Straight Back '69 Cub #3...Mr. Cub. Looks like they snapped a shot at Shea. This picture has been used on many cards, including the mini die-cut from 2014.