Winkler's academic career began as a history fellow at the University of Texas. In 1899, the university acquired the
Bexar Archives, a collection of written artifacts which documented Spanish and Mexican rule in Texas. In the summer of 1900, Lester Bugbee assigned the task of cataloging these documents to Winkler, where he obtained his on-the-job-training on preserving and archiving old papers. He taught history at
Blinn College for the fall term. In 1902, he studied briefly under
Frederick Jackson Turner at the
University of Wisconsin–Madison. He returned to Blinn the next year, while also working for the Texas State Historical Association as a administrator, editor, and writer. During this period, he also expanded his paper on the
Cherokee and prepared a version of it for publication. ==Death==