Second from the bottom in your “More Medicos and some very cool ones” picture looks like an LHS Sterncrest pipe. Can’t see the logo cleary but it looks right. They were one of the main pipe suppliers for american soldiers in WWII, stopped making pipes in the 60s. Given that yours looks like it says “imported briar” under the logo its probably a post war pipe, but still some cool history in that company.Now some Grabow and Medico pipes he probably bought over the years at drug stores or possibly the Comer's shop that used to be in Iowa City.
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These are interesting; something, Grabow, and Wally Frank:
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More Medicos and some very cool ones:
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