I have a Old pocketwatch bob medallion that shows an old caterpillar crawler tractor doser shown. Does this have any monetary value?

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If what you mean by medallion as being a watch fob, then there are some listed on the following link as well as prices. Caterpillar, Watch Accessories, Wristwatches items on eBay.com=

The prices range from about $5.00 up to $40.00. There is also one listed for $202.50. But, I don't know what yours looks like.