I've got 12,850 Cubs cards from 98 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1978 Kelloggs #48 Bruce Sutter Looks like the picture was taken at Candlestick in 1977...I'm pretty sure the orange seats are Candlestick and I'm 100% sure that the black band on his left arm was worn in 1977 after owner P.K. Wrigley died. Sutter was 8-10 in 1978. Hard to imagine a reliever today having 18 decisions.
1980s: 1989 Upper Deck #494 Al Nipper Upper Deck gave him a card in the set, but Nipper didn't pitch for the Cubs or any other MLB team in 1989. The Cubs released him in late March, '89. He spent the entire season out of baseball but returned for a brief fling in 1990.
1990s: 1994 Pinnacle #254 Turk Wendell Pinnacle gives us a nice look at the quirky Wendell jumping over the foul line on his way back to the dugout. He spent most of the 1994 season jumping lines in Iowa and other AAA cities. His stay with the Cubs was just six games in May and June. His 11.93 ERA didn't have any of the Cubs brass jumping for joy.
2000s: 2009 SP Legendary Cuts #38 Carlos Zambrano I just realized that the card number matches Zambrano's uniform number. The 2009 season was a mediocre one for the pitcher that was being paid to be the ace of the staff. For a mere $18.75 million, the Cubs got a 9-7 record. $2 million per win....pretty expensive.
2010s: 2012 Topps #494 Darwin Barney Gold This is one of the eleven Flyin' Barneys in my rainbow. The gold cards came in the update set and are /2012.