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Melanie, you might be able to get an answer from the American Truck Historical Society.  They are devoted to the history of commercial trucking, and have some very knowledgable folks.

Be sure to send them all the photos, including the Teamsters St. Paul local button.  My hunch is that the cap is from a Minnesota trucking company.  You can email the American Truck Historical Society at:

info@aths.org

Ive been thinking rhe St Paul area might be a better area to look at.

I also looked at some vintage advertising cut art books with no luck so far. But also that the hat or logo would be appropriate for other deliveries such as florists too.  I chose a few with Native Àmerican representation, but don't overlook the the fuzzy Mercury as food for thought.  À red cap or vest definitely implies a service and could even be strictly for RR delivery by company X.   

 These are approved logos for book owner ad creations in 1939.(see"keyline")

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I think Pontiac is closest so far.

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Since my last post, I have gone as far as I can on all of your leads.  My last shot was sending a note to the American Truck Historical Society (Thank you, Tom Number 90).  After that, I shall toss this thing in the Goodwill donation box so it is out of my sight.  So odd that after the tonnage of items we have either listed on eBay, posted on Facebook Marketplace, or handed back to the estate seller to give to his favorite swapmeet seller, this was a thing that I felt needed scrutiny.  Insanity on my part!  If this lead runs dry, it's buy-bye cap!  Thank you so much, every single one of you.  My next posts will be completely amateur train questions which will likely get me snarls, maybe get me tossed out!

Oh JD, (JD2035RR) about liquidating track.  Geewhiz, thus far the track has been the bain of my existance.  There really are hundreds of pounds of it in various sizes and configurations, from many eras (based entirely on the degree of dust and oxidation I see)...some sparkly clean, some that look like I should get a tetanus booster before I dive into it!  I am dipping my toe into it by listing some Gargraves track in original boxes.  The first 3 boxes are pretty straight forward, the next box has me confused.  I am going to post a question about it on a different thread, I'm a bit apprehensive about posting what will certainly be the first of many juvenile questions asked in a group such as this, but Adriatic convinced me to grow thick skin, so I am ready!

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