A matching set of plaid Skyway luggage.
The Chautauqua Industrial Art Desk was made, as far as I can tell, by Lewis E. Meyers & Co. from the late 1800’s into the early 1900’s as a home schooling aid. With interchangeable scrolls on topics ranging from art to Christianity to, apparently, poster making, the desks were sold door to door and are now pretty rare. They featured a map on the outside of the lid:
I didn’t even ask what he wanted for the desk; these can go for hundreds of dollars without the base of the desk intact, and this was in what appeared to be completely unused condition. If you want one to restore, there are a couple for sale right now here, here, or nearly complete here.