Well, this one kept niggling in the back of my brain. So I spent a little time going thorough the catalogs to find it.
The only listing I could find that came close to a match for this model was from 1935. 1934, no. 1936, no. There are also Atlas DP's offered in 1935. It seems that in 1936 Craftsman had switched completely to Atlas for their DP's.
Here is page 22 & 23 from the 1935 catalog. You'll notice that the DP in the OP's picture has 4 handles, the picture in the ad has only 2 (one handle going though the spindle). It wasn't until 1938 that Atlas used 4 handles on their DP's (IIRC), so I think this handle assembly was added to this DP at a later date.
It seems that this DP was only offered in 1935 and even though it has the Craftsman name cast into the side, it may have only been offed under the Companion brand (the precursor to Dunlap).
Mike - for some reason, the second picture that you posted won't open for me. Could you repost the picture of the opposite side of the DP for posterity ?