[Joe_G.]

Hello Chad,

Chicago was issued cards in 1887, 1888, 1889, and 1890 as follows.

1887 - NL (Chicago White Stockings)
1888 - NL (Chicago White Stockings) & WA (Chicago Maroons)
1889 - NL (Chicago White Stockings)
1890 - NL (Chicago Colts)

NL = National League
WA = Western Association

In terms of difficulty, there are some extremely scarce cards including the 1890 National League cards, some of the Western Association players as well as the three Chicago players/mascot found in the 1887 short numbered series. McCormick, Williamson w Mascot, and the Mascot card itself (extremely tough) comprise the Chicago players found in the short numbered series. Note that 1887 includes a "short numbered" and "long/leading '0' numbered" series. Outside of the short numbered cards of 1887, most of the White Stockings cards are relatively common other than a few specific poses such as Anson in Uniform.

Perhaps the most collectable sub-series of cards would be the 1887 leading "0" numbered cards for which 12 players are represented among 63 poses. These cards are relatively available but the team's biggest star, Anson, wasn't issued a card until the following year. Obtaining one card of each player in the 1887 "leading '0' numbered series would be very attainable, affordable (wrt other options), and pleasing to the eyes with a common card design.

If you really want to get to know the fascinating Old Judge set, I would recommend the book "The Photographic Baseball Cards of Goodwin & Company (1886-1890)".