UPDATE: The Smithsonian Institute has one of these tokens in their collection as part of their National Museum of American History. According to their website, these tokens were made in the early 20th century by the Scovill Manufacturing Company of Waterbury, Connectictut. Scovill made, among other things, buttons, tokens, coins, and medals... and staplers, as my mother had a Scovill stapler at her desk for many years.
Recently found these two tokens in a group of donations to the Legacy Knights Numismatic Society's YN auction. They are Chicago Transit Authority tokens. At first I thought they were two of the same, but upon closer look, they are two different varieties.
I put them together in an elongate 2x2 to keep them together for comparison. Since I can't tell obverse from reverse on these, I'm calling the side with the staples Side A and the side with the staple legs Side B. If you look at the staple positioning from photo A to photo B, you can figure out the orientation of each. I flipped the 2x2 over like turning a book page (side to side)... so the first variety is on the left in photo A and on the right in photo B and vice versa.
The first one has a different designs on Sides A and B. Side A says "* CHICAGO TRANSIT * AUTHORITY" surrounding the monographic "CTA"; while Side B says "* SURFACE SYSTEM * TOKEN" surrounding the monograph. It has a nearly perfect coin orientation to the strike.
The second one has the same design on both sides: "* CHICAGO TRANSIT * AUTHORITY" surrounding the monographic "CTA". This version has neither a coin orientation or medal orientation (although it is closer to coin orientation).
Some off-the-cuff observations I've made before looking into any sort of reference on these tokens, based on my limited knowledge of coin and token manufacturing:
1. I don't know which of these was minted first; but based on a general principle that as time passes cost-cutting measures based on simplification are employed, it would seem to me that the one with different designs on opposing sides would be an earlier variety, as making two different hubs for dies would have cost more than making duplicate dies from a single hub.
2. Because of the haphazard orientation of the variety with the same design on both sides, I don't know if the coin orientation on the "surface system" variety was intentional or accidental. However, the lack of orientation on the duplicated-design variety might have been part of a cost cutting measure (if it indeed was a later variety).
3. Both sides of the duplicate-design variety appear to be struck with dies from the same hub, unless someone else can spot die differences.
4. The Chicago Transit Authority design differs from one token to the next, indicating their dies were made from different hubs. Note the size of the stars from one variety to the other. The stars on the duplicate-design token look smaller than the bold stars on the other variety. Compare the positioning of the web of squares behind the stars and letters also. There are lettering differences also.
5. At this point I haven't figured out if the slotted holes were put in the blanks before, after, or during the striking process. I haven't seen any known error versions of these tokens or studied how these types of holed tokens are made. Does anyone else know? If so, please tell me in the comments.
As mentioned above, these were donated to our club so they will be going in our annual end-of-the-school-year auction. Some LKNS YN will enjoy them. Maybe they will figure out more of their story. Please post any additional info you may have about them in the comments.