I identified the $1 chip several months ago via the records mentioned below. I had sold many on this board for about $5 each, then kept getting much more in eBay auctions. Your chip even looks like one of mine, what with the "smeared" hot-stamp imprint..

From my auction write-up:

DESCRIPTION: I recently got and identified this chip via the manufacturer records on David Spragg's Preserving Gaming History page. The manufacturer's card and both sides of the chip are shown in the scan above. In 1926 Benny Binion opened his own permanent craps game in room 226 of the Southland Hotel, Dallas TX (the hotel was owned, by the way, by Sam Maceo, the Galveston mob boss). In 1928 he added policy (numbers game) and other games to his operations. The room was headquarters for Binion's gang, called the "Southland Hotel Group" or "Dallas Syndicate." In 1946 Binion expanded his operations to Las Vegas. Return privileges.

Binion's right hand men at the Southland were Ivy Miller and Red Scarborough. Note that Ivy Miller's name and Southland Hotel, Dallas, Texas, make up the shipping address for the chips, on the card -- the same chip sold here -- same harp rim mold, gray color and style of $1.00 and horseshoe imprint. (Binion must have liked the horseshoe design -- his famous casino in Las Vegas is named "Binion's Horseshoe," of course.)

Robert