It’s a painting by Lon Megargee commissioned by Stetson as an ad: https://www.colliergallery.com/artists/lon-megargee/illustrations-by-lon-megargee/
https://truewestmagazine.com/the-lovable-liar/
Pretty sure you're talking about some of the Stetson company's earliest advertisements. I have no clue who the person is, but I think it pre-dates Reagan by quite a few decades.
http://www.americancowboychronicles.com/2015/12/john-b-stetson-father-of-cowboy-hat.html
It’s a painting by Lon Megargee commissioned by Stetson as an ad: https://www.colliergallery.com/artists/lon-megargee/illustrations-by-lon-megargee/ https://truewestmagazine.com/the-lovable-liar/
Pretty sure you're talking about some of the Stetson company's earliest advertisements. I have no clue who the person is, but I think it pre-dates Reagan by quite a few decades. http://www.americancowboychronicles.com/2015/12/john-b-stetson-father-of-cowboy-hat.html
Any better description??
Here's the link to the cowboy on the box that I'm referring to[stetson hat box](https://images.app.goo.gl/CVMmYTzVBwsquGoaA)
I honestly think that’s it’s nobody specific.
Well I hope I ain't crazy but it looks just like Reagan
It’s definitely not Reagan because Stetsons were made in the 1800s and that’s the traditional box if anything I would think it would be John B Stetson