Five Random Cubs Cards

 I've got 21,062 Cubs cards from 316 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.

1900s - 1970s: 1909 T206 Pat Moran Moran was a part-time catcher for the Cubs.  He played in no more than 77 games, so it is a bit of a surprise that he was a part of this set.

1980s: 1985 Team Issued Leon Durham This cards in this set were sponsored by 7-Up and given away at Wrigley Field on August 14.  The Expos beat the Cubs that day 8-7.  Durham was 1-4 that day.

1990s: 1990 Donruss #275 Mitch Williams Donruss snapped a shot of Williams in Mesa in 1989. That was the last season the Cubs wore pullover jerseys.

2000s: 2002 Ovation #109 Sammy Sosa The 2002 Ovation set has 120 cards.  The first 89 are common players.  The last 31 cards belong to just six player, so they each have five plus one card that features all five.  Sammy was one of the super six.  This is the last of his five cards.

2010s: 2016 Topps Now Off Season #38 Wade Davis  Davis became a one-year rental, costing the team Jorge Soler.  Davis saved 32 games for the Cubs in 2017, so I think the deal was worth it.