This was scheduled to run yesterday, but it got bumped by something more important. I've got 14,459 Cubs cards from 109 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1900s - 1970s: 1969 Jewel Ken Holtzman A star from the 1969 team that didn't make it.
1980s: 1987 Donruss #447 Scott Sanderson A star from the 1984 team that didn't make it.
1990s: 1990 Kaybee Toys #8 Andre Dawson A star from the 1989 team that didn't make it.
2000s: 2007 Heritage #66 Matt Murton A member of the 2007 team that didn't make it. Sensing a theme yet? The RNG really like players from team that... well, you know what they did (or didn't do).
2010s: 2013 Topps #299 Darwin Barney Silver Slate Darwin never played on a good Cubs team. The most wins any Cub team had during his time in Chicago was 75. But he was a member of the 2016 Blue Jays, a team that didn't make it.