We're Jet and Craftsman the same product 20 years ago?
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No. Jet never made drill presses for Sears Craftsman.
I agree this appears to be Craftsman DP but I don't think it's 20 years old. I think it's 80s vintage - likely the last of the made in USA drill presses Sears used to sell. I bought one new in 97 and aside from the difference in style, it was made in China.
This one looks really rough. It hasn't been overhauled - it was painted (WHY?!?), nor was it well taken care of. It was ridden hard and put away wet. The seller is either a shyster, or hasn't a clue what they're talking about. I wouldn't pay $50 for that DP.
If you're in need of a DP right away, keep looking on CL, OfferUp, FB Marketplace, etc. If you're anywhere near a large city, drill presses will be readily available for much less money.
Good luck!
Brian