In the autumn of 1894, during the heyday of railroad migration through the Indian Territory, Chicago, Rock Island & Pacific Railroad purchased the Choctaw, Oklahoma & Gulf rail lines running through the Seminole Nation. Over the next year, Rock Island Railroad developed the railway into a 120-mile route running from the Indian Territory coal mines of McAlester, to the industrial and commercial centers in the Oklahoma Territory. Situated as it was near the western boundary of the Indian Territory, a portion of the line ran through Wewoka - a sizable trading post and capital of the Seminole Nation.

In the early years of the twentieth century, Rock Island established a new depot in Wewoka and built a switching area. The switching area, or “siding,” extended over a half-mile in each direction from the station. This “switch”, as it was generally called, was the largest such system of Rock Island’s west of the Mississippi. Merchants, traders and businessmen for a radius of thirty-five miles ordered goods and supplies, which were then shipped via railroad to the nearest siding. They drove in wagons to accept delivery of these items. In this geographic area, they were shipped to the Wewoka Switch.

In the 1920s, oil was discovered southeast of Wewoka and virtually overnight, the quiet community became a busy, crowded city, teeming with the hustle and bustle of thousands of new occupants. The local population soared from 2,500 to 20,000 in just a few months. Oil field supplies, parts, pipe, casing, drilling rigs and other equipment flooded the Wewoka Switch. Adding to the confusion was the fact that every merchant's stock orders were doubled, tripled, and even quadrupled to meet the voracious needs of the swelling population.

The Boom was on! Lost freight bills, inadequate telephone service, small railroad facilities and other factors added to the immense congestion. Thousands of freight shipments designated elsewhere, thought to be lost in transit, were found hidden in the Wewoka Switch. Local merchants, upon being questioned about late or lost orders, had a standard and faultless reply of, "Yes, I have it, but it's caught in the Wewoka Switch!" - meaning, of course, that they had been unable to retrieve the delivery and were caught in a "tight spot". So common was this confusing situation, that Rock Island Railroad actually adopted a policy of looking for all "lost in transit" merchandise at the Wewoka Switch before searching elsewhere. To save time, they prepared rubber stamps declaring "Search Wewoka Switch" for all missing shipments. The expression, "I'm caught in a Wewoka Switch" grew to mean and imply that one suddenly found himself in a bind or trying, precarious situation. The expression became standard with oil field workers and promoters alike.

In later years, these same oil men, drillers and roughnecks, moving on to bigger and newer oil discoveries, carried the famed phrase, "I'm caught in a Wewoka Switch", to all parts of the world, where its use became universal. Today, it’s a nod to Wewoka’s storied place in history.