I bought this 21 jewel 12s Illinois watch marked "Winner" on ebay for $63.50 last month. The serial number is 5073268 from 1928, and it is a Grade "279". This watch shows up in the serial numbers list in Meggers and Ehrhardt Illinois Watch Co. encyclopedia in only one run of 25 watches (5073251 - 5073275). There is another run of 30 watches annotated with "Ill. Winner", but these are Grade "305" which is 16s. Not only is this a rare PL watch, but I have not seen this damaskeening pattern on an Illinois watch before.
Just imagine the proud owner getting this WINNER watch on "Nov 28, '28" as is inscribed inside the case back. Little did he or she know that only 11 months later, the stock market would crash and the Roaring 20s would be over.