Hugh Chisholm, whose father came to the US from Strathglass Carries, Scotland, was a wealthy entrepreneur in the East Coast paper, railroad, power generation, and airline industry. He bought vast land near the Potomac River and built his estate, called Strathglass. He also owned one of the largest yachts on the Potomac and used it to entertain the most powerful men in Washington, including presidents. In 1934 he bought a new Ford chassis and had this unique "Woodie" wagon constructed to shuttle guests to his yacht.
Crucible Steel Company carried out the extension; the 100% oak body was built by Olson Extension Company near Detriot. It seats up to 13 people with room for luggage and what appears to be a custom tailgate ramp for a wheelchair, which is suspected may have been designed to accommodate President Roosevelt.