I've got 14,493 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: 1964 Topps Stand-up Billy Williams They've got Billy looking like a left-handed second baseman on this.
1980s: 1988 Topps #186 Rafael Palmeiro He was an All-Star with the Cubs during the 1988 season and a Ranger after the season. GM Jim Frey needed a closer and getting one would cost the Cubs Palmeiro or Mark Grace. Grace stayed, Palmeiro went.
1990s: 1997 Score #460 Mel Rojas What a bust of a free-agent signing this was. The Cubs signed him for three years, $13.5 million. They got half a year out of him, an 0-4 record, an ERA of 4.58, and just 13 saves in 54 games. In August he was traded to the Mets.
2000s: 2007 Donruss Elite Green #9 Darwin Barney This makes two straight weeks that he RNG picked a card from the Barney collection. Darwin's card partner Mitch Canham didn't have Darwin's success. He never made it to the majors and had just brief spells in AAA.
2010s: 2104 Donruss Breakout Hitters #18 Anthony Rizzo I created my own version of this card when it came out in 2014. If you're showing brick on a Cubs card...