The TStL&W originated with the Toledo, Cincinnati and St. Louis Railroad, a company formed in February 1881 as a consolidation of several smaller, narrow gauge lines connecting the Ohio cities of Toledo and Cincinnati with St. Louis, Missouri. Soon in financial difficulties, the company dropped its Cincinnati arm and reorganized in June 1886 as the Toledo, St. Louis and Kansas City Railroad and over the next two to three years widened its lines to standard gauge.
The following constituent companies formed the Toledo, St. Louis and Kansas City Railroad:
The Toledo, St. Louis and Kansas City was reorganization in 1900 and renamed as the Toledo, St. Louis and Western Railroad. It operated 450.72 miles of line between Toledo and East St. Louis. The Clover Leaf became part of the larger New York, Chicago and St. Louis Railroad (the "Nickel Plate") on December 28, 1922.