Extraordinary Aviation Pioneer: Clifton Penn “Ole” Oleson

Have you ever heard of Clifton Penn Oleson, better known by his nickname “Ole?” Unless you are a serious aviation buff or have spent time in the Midwest, particularly in the state of Iowa, it is very unlikely. By any definition, however, “Ole” Oleson was a true early aviation pioneer. His phenomenal aviation career included being a military pilot during both WWI and WWII, barnstorming, flying early mail routes plus a number of other noteworthy general aviation activities. Records maintained by the Iowa Aviation Museum, located in Greenfield, Iowa, confirm that Oleson performed flying feats that equaled or exceeded many of those of his contemporaries.

Some of the material for this article was obtained from Oleson’s nephew, Mr. Earl F. “Spike” Olson (not Oleson). While conducting research for this article, it quickly became apparent that the state of Iowa had spawned a phenomenal number of early aviation pioneers. For anyone motivated to learn more about early Iowa aviation history, the following book is recommended as a starting point: Eastern Iowa’s Aviation Heritage, by Scott M. Fisher.

When I was 12 years old, “Ole” took me for an airplane ride in a Model B Curtiss Robin aircraft, powered by a Curtiss OX-5 engine. Of course, at the time, I had no idea what an aviation celebrity the pilot was. Aviation (including space) pioneers probably receive more public acclaim and accolades than most other professions. It would be nearly impossible to name all the individuals considered pioneers that are interwoven throughout aviation’s long, interesting history; therefore no attempt will be made to do so at this time. Unfortunately, the element of time gradually diminishes all aspects of history, even those related to aviation. It is important to remember that, when “Ole” Oleson and his contemporaries were in their prime, worldwide, real-time communications had not yet become available. The author knew “Ole” Oleson and a few other members of this nearly extinct fraternity of old aviators. For some reason, however, the memory of “Ole” Oleson is etched in the author’s memory more than the other members of this elite group.

Oleson’s story begins in 1900, with his birth in McGregor, Iowa. People who knew him during his childhood stated that even then he expressed interest in anything to do with airplanes. In 1917, at the young age of 17, Oleson graduated from the Curtiss Flying School in Miami, Florida. During the graduation ceremony he was awarded pilot license number 67, making him the youngest licensed pilot in the United States. The following was extracted from an undated newspaper . . .